Singledom

It's about 10AM on a Sunday, and I am sitting on my balcony, scanning the dating sites.  "You have a new Match!" pops up on Match.com. I take a look. I'm pretty sure I have not seen or "liked" this woman, so I am not sure how we are a "Match". Maybe I liked her after a few too many Manhattans. "Swiping" or "Liking" seems very mood dependent. Some are a no-brainer, but others I could be on the fence about. If I'm feeling pretty good at that moment, I will pass on them; if I'm not, I might just take a shot.

With the exception of Bumble, either party can initiate an in-app chat. Bumble gives that power exclusively to the women, which I originally thought was a good idea. But some women have told me that there is no way they are going to initiate. Regardless of the app, guys have to do more work. We have to do all of the clicking, swiping and liking, and women get to sit back and react... or not. It's not that guys don't get the occasional ping from the other side of the wall, but it's rare, so we swipe and like.

"Hi Vanessa! I see we are both into cycling :)" I initiate. Bing! "You matched with Vanessa!" "Hi Steve, yes I loooove cycling!" she replies. "Awesome! Where do you like to ride?" I send. No reply... ever. It used to annoy me, back when I first started, but I now realize it is just the nature of the ecosystem. Each of us in this world have our own lives, and we are all at different stages of interest around dating. More often than men, women may have a few bad experiences and then drop off. They usually pop back up later... a little more jaded than they were before.

Communication seems to suddenly end, for no apparent reason, at all stages. Was it something I said? No, I would never say anything that would cause a woman to stop talking to me. I know many men do... probably because many are just fishing for sex. I think Tinder probably lowered the conversation level, even though it has since been homogenized to be like all the other apps.

I find myself adopting the communication etiquette of women, which seems to be primary based on not wanting to look too eager, or desperate. For example, if you were the last one to send a message.. you should not be the next one to. If it goes unreplied to... you probably have your answer. The exception is the machine-gun texter, which is me.  I am the opposite of what I call the cannon texter. I was chatting with a woman once, who would send single texts that were four pages long. She obviously took her time to think about a lot of things to say at once. Maybe she did not want to be interrupted, or sidetracked. I'm the opposite, I click send at the end of each thought, then realize I had another thought, usually about four times in a row. It's always fun when you have two machine-gun texters going at it, the conversations tend to get jumbled up. "Darn, my flight is delayed! :(" she texts. "But, I get to see my daughter when I get home :)" she texts. "Well that sucks :(" I reply. "Why did you say that?" she texts, "I was responding to your previous text." I reply. So you see how that goes.

Conversations abruptly ending is part of the natural order of dating. I'm not really complaining, if none of them ended, I would be on my phone non-stop. You ultimately learn that you need to have a certain number of them going on, knowing that most will stop, but enough won't, that you can actually meet people. But abrupt endings don't stop once you meet people. Nothing really matters until that first meeting, everything else is just bullshit leading up to it. That first meeting can go well, or end in a "He/She is just not that into you". While I have heard about it happening, I have not yet been on any date that ended in the middle of it. I will take that as a good sign. But I have been "ghosted" a couple of times afterwards. I'm a gentleman, if I did not feel any spark, I don't just ghost, I will more likely send a message like, "Hey, thanks for meeting last night. I think we can both agree that neither of us felt the spark we had hoped for. I wish you luck in your search." Regardless of how she may have been feeling about me, I want to let her save face as well.

Match keeps all your chats until you delete them, and I was looking back at some of my first initial messages from 3 months ago, when I started. I have clearly improved on my initial message skills since then. But still, lots of unanswered messages. The funny thing is, those women are all still here...

 

 

My ex and I remained friends after our split... well.. not immediately, but a short while after the dust had settled. We had bought a ShiTzu puppy together about a year ago. She kept him, he was "her" dog". She had asked me if I would be interested in taking him for a few days, one time when she was going out of town. I said I would in the future, but could not this time. So he went to a kennel. I felt bad for him.

"Hey, can you watch Jax next week?" she texted. "Umm, sure how long?" I replied. "Only 8 days." she texted. Eight days! I'm in full-time dating mode! I definitely recall him being a lot of work, but the alternative would be eight days in a kennel. "Sure." I replied. This will be interesting, my apartment building is full of dogs, and he always goes nuts around dogs. My apartment is also on the 20th floor.. could he make it without relieving himself in the hallway to the elevator? I guess we will see... besides, chicks love cute dogs... right?

I had recently taken up cycling again. I used to really enjoy it, but then did not have time. Well, I have time again, so I pulled the bike out of storage. It's a pretty bad-ass bike. I can't do the official bike shorts, because I don't like my nuts ending up behind me, so I just wear mid-length black running shorts. Together with black Nikes, a black long-sleeved Underarmour shirt, and my reflective blue Costa's on the front of my bald, tanned head.... I look pretty bad-ass also. I had been riding up and down the Tampa Riverwalk and Bayshore Blvd, and getting my share of looks from the females I whizzed past. Maybe it was the bike... or my almost clipping their elbows as I passed.

It was in the back of the closet. A basket I had bought for the front of my bike, to carry crap when my ex and I used to ride. It does not belong anywhere near a bad-ass bike, but if I wanted to ride this week, I would need to take the puppy. So the basket goes on. Maybe it's good, chicks love cute puppies, and bad-ass looking guys on bad-ass bikes.

Sunday afternoon, the Riverwalk is always packed with people. Ordinarily, I would continue my game of seeing how fast I could ride through crowds of people, without hitting one. But today, I will put Jax in the basket up front, and go slow. Not only might he jump out, but I also want to be able to stop quickly for any women that want to pet him. As expected, we are stopped many times... he really is a super cute puppy. One time we stopped, so a woman could pet him, in front of a large window. I looked over, and saw in the reflection... the gayest looking motherfucker I had ever seen. A German Shepard, Doberman or Labrador running along next to me would have been fine. But this little fru-fru puppy, super cute though he is, killed my entire persona.

Dating with a dog is... unconventional. He's still a puppy, so leaving him alone in my apartment is not an option... he would bark nonstop. I have him until Sunday, but I don't want to wait that long. "Any plans for tomorrow night?" I text. "Not yet." she replies. "You do now!" I text. "Great! When/where?" she replies. "Somewhere pet-friendly." I text. Long pause. "You never mentioned that you had a dog?" she replies. "Only for this week." I text. Long pause. "Do you have to bring it?" she replies. At this point, I am not sure what she is thinking the dog is, but she clearly does not seem crazy about the idea. "Unfortunately, I do, he's a puppy. Small and super cute!" I text. I am hoping she does not want to put it off until after Sunday. "Sure, why not." she replies.

 

I had been seeing this 40-year-old nurse for a short time. I'll call her Rochelle. It felt like things were going well. She had a sarcastic personality, that I found myself liking. Sarcasm in text is complicated. You have to really know a person, and I didn't know her, so I often took her quips wrong.

I would pick her up at the hospital after work, between 7:30 PM and 8:00 PM, and we would go grab dinner as we got to know each other. She was not an easy person to talk to... lots of one-word answers. I was starting to get the sense that maybe we were not clicking, because I know what clicking looks like. Our conversations often felt like a test of my mind-reading capabilities. I have been around a while, and been in relationships before, long enough to know that my mind-reading skills are shit, even when I know the person very well. For some reason, women seem to have this undying hope that we will "Get them". Eventually we get better, but we never reach the level most women expect.

In spite of the stilted, and sometimes confusing, conversations... I still liked her. One evening, instead of going out after work, we came back to my apartment. I knew she had to work the next day, so it would not be a long visit, but things needed to either progress, or stop. One thing led to another, and we're making out on the sofa. It was good... it was progress... I was keeping an eye on the clock. At about 10:30, I figured we needed to stop our fun so I could drive her home... about a 30 minute drive. She did not disagree, but walking to the elevator down the hallway, she started making comments about me kicking her out early. Some clarity on when she really needed to leave, would have been nice to have had earlier.

The next day I get a text saying something like, "Hey I was not feeling the spark, etc.". I was okay with that, I was not feeling like we were in sync either. I still liked her, but it was time to move on. I setup two first dates for later in the week with two women that were around 50-years-old. Maybe my mindset is changing. A dinner with one on Friday, and a Lunch with the other on Saturday.

"What are you doing?" Rochelle texts me. "Moving forward!" I reply. "With other women?" she texts. "Two dates this week with 50-year-olds." I reply. Some time goes by. "We both know that you don't want a 50-year-old, you want a 40-year-old." she texts. "And we know that how?" I reply. "We know that, because you are going to cancel those dates, and take me out instead." she texts.

Hmm, I have to think about this. I have two dates setup with lovely seeming women, but I can't help but think Rochelle and I have unfinished business. She can see me Friday, and I think about keeping my Saturday lunch date, but then decide that would be unfair to that woman. So I reluctantly cancel them both. I was honest about it, telling them that there was some unfinished business with another person. Neither of them had met me yet, so it was fine... ish.

I pick up Rochelle after work and we head straight back to my apartment. Uber Eats brings us some food, and we start making out again, but this time it keeps going on into the bedroom. It seems we did have some unfinished business after all. I thought it was pretty awesome, and it seemed like she did as well. So much for missing sparks. I drove her home. On my ride back, I was thinking about how this had completely turned around. She suddenly occupied the front of my brain. The next morning I put myself on invisible mode on the dating apps, and sent flowers to her at work.

Rochelle has a busy work schedule, along with an 8-year-old, that she seems to have custody of most of the time. Our next in-person meeting opportunity was vague. I can live with gaps between seeing someone. Especially if we are communicating... but she is not much of a communicator. Unable to answer texts at work is completely understandable, but when you are not? I was starting to think, even though we had an awesome night, that something was missing. It felt as if I was "parked" in a box, that she would open when she felt like it. She was not opening it nearly often enough.

For all of our tough "We don't really give a shit" attitudes, like plants, men need watering. Also, like plants we can be over-watered... but no water is worse. Women are more vocal about their need for attention, but ours is just as strong. I am sure that if left alone, she would eventually open the box and let me out. Maybe she assumed I would just sit there, parked, until she had time, but life is just too short for that. I don't have any issues with a woman who has kids at home, provided they are able to make time for a relationship. "Emotionally available" is not enough... a woman needs to be "Physically available" also. I wonder what those other two women are up to...

 

Every single person over 15 years old has an ex. Maybe an ex-girl/boyfriend, ex-wife/husband, ex-2nd wife/husband, etc. Most of the time, exes are bad memories, sometimes they are not.

When there are kids involved, as there usually are, exes can be a sore spot. Thankfully, my kids are grown from my first marriage, and we did not have any in my second. The split with my second wife was "technically" painless, but there is always some pain in a split. Well, maybe not always, according to some women I have dated. I am feeling that I got lucky.

My ex and I are friends now, we chat almost every day. We started as friends, and 12 years later, we came back to where we were at our best... friends. She and I are in similar situations, we are both dating, and we are both hopeful that the other finds happiness. I tell her about all of my dates, and she does the same. We kind of compare notes. She will frequently send me screenshots of some chat she is having, to ask "What did he mean by this?" She is a smart, kind, beautiful woman, and eventually she will find another guy that appreciates that, and she'll be fine.

19-1/2 years was our age difference. I did not set out to be a cliche, it just sort of happened. I remember seeing other older men with younger women before I met her, and thinking "there's Sugar Daddy", what a creep. But when we first got together, I was broke. I literally had to ask her for gas money, and she was living paycheck to paycheck. Fortunately, my broke spell did not last long. It was a rocket ride after that, apartment - to house - to bigger house - to even bigger house, etc. From driving a shitbox old Honda Accord when we met, she was driving a brand new Mercedes coupe when our run ended. From her having never been out of Hillsborough County before, we traveled everywhere. Our time together was very... productive. It was a great run, I don't regret a minute of it, nor do I regret it ending. It had run it's course.

There was a time when marriage was meant to last forever "Till death do us part" and all. It was how I was brought up, and my parents reached that goal; 62 years together before my Dad passed. I don't think it works like that anymore, that is a bygone era. I stayed in my first marriage, for probably the last ten years of it, because of this hard-wired thinking. If I could do it over, we would have skipped that last ten years together, neither of us were happy. Instead, I could have spent that decade with someone else, and been happy, as I ultimately was, a wasted decade later.

"You should find someone your own age." said my Mom, to my newly single self, as you would expect your Mom to say. I looked. It is not so much a physical thing, there are plenty of beautiful women in their 50's. I think it's the mental age difference that I struggle with more. 12 years with someone a generation younger, can alter your thought patterns, probably not permanently, but I am still in that mode. Sorry Mom... not gonna happen, but I am not "targeting" 4o-year-old women either; while my dating app range does go down to there, it goes up to 55. Some of my friends say I am wasting my time, that women that young would never go for me.... but they have, and they do. They don't seem to grasp that... usually... women fall for the person you are.

It does not bother me when a woman talks about her ex on a date... to a point. Our exes, good or bad, are a significant part of our lives and history. Some women seem to struggle with the idea, that my ex and I are still good friends, probably assuming there are "benefits" involved. But that is not the case, nor is that the kind of relationship either of us wants from the other... if it was, we would still be together. No, we are both excited for the future, the next chapter, hoping it will be at least as a good as the last... but new.

There is no better time in a relationship than the beginning. I'm not saying it goes downhill from there. But the discovery and passion, will eventually give way to stability and security. It takes work to keep the passion alive, from both sides. If you are not focused on that as a priority, you will look up one day and think, "too much effort". Once that fire is allowed to go out, it is difficult to re-light. The the idea of a brand new fire, starts looking better.

As I am writing this, how old is the woman I am seeing at this moment? 40.

Regardless of how amicable the split may be, relationships ending are tough. The toughest part is usually less about the ex, and more about suddenly being alone. It may not necessarily be her that you are missing, so much as just a human being in her old spot. Attached to your hand, laughing at your jokes, or yelling at you for talking over The Batchelor.

Single for less than a week, I got pinged by a 40 year old Brazilian girl, with broken English. We moved to text and chatted for a while, before I, probably too eagerly, suggested that we meet. While still chatting, she ended one conversation with "Good night, my love". I guess that should have been a flag. I did little bit of research on Brazilian women, and it seems that terms like "Love", are not what we Americans think when we hear them. It is more the equivalent of "You're okay so far."

We meet, she is cute, very petite, missing the infamous Brazilian ass, but I'll survive. She can't speak a word of English, and had apparently been using a translation app to chat with me. Second flag? What the hell, she is nice, and filling a void in my life. She lives in Town and Country and has no car. Turns out she lives in an apartment with a girlfriend from Brazil. Thank you Uber!

We quickly get into a pattern, weekends we are going out, and many weeknights she is Ubering over. We mastered the translation app for live conversations. It did not take long for people in restaurants to realize how we were speaking to each other. I did not mind, it was kind of a novelty... our "thing". This would later get old, but for now it was kind of fun.

There was no watching TV, because she could not understand the dialogue. So our relationship was pretty much just non-stop sex... which seems to be a universal language. I could tell she was falling for me, maybe too hard and too fast. This made me nervous, but I let it go, since the alternative was sitting home alone. Yes, in hindsight, I am aware that this was a totally selfish, dick move. I realized she was not the one for me, because the entire month we were seeing each other, I remained on the dating sites, chatting with others.

Eventually non-stop sex gets boring. I know, hard to believe a man saying that, but it seems that it's true. Blew my mind also. Suddenly, I am feeling really shitty about myself. I allowed this girl to continue to fall, knowing she was not going to be my "person". I went through my "What if" thought process again, and still saw nothing.

I had planned to let her down easy on a Friday. I had another date lined up for Friday. I know, I know. It gets worse. My date cancelled. I swear I was going to text the Brazilian to say, "Hey, this is not working out, etc.", instead I texted "Uber?" This had become our code word for me dispatching an Uber to bring her to me. I was, you will be glad to hear, wracked with guilt when she arrived. I was not reaching for the phone to translate as often as I had before. She knew something was up. Her instinct was to have sex, to pull me back from wherever my mind seemed to be going. We did... my mind did not change. Yes, I feel bad about that too.

Her response to my text the next day. saying something like " Hey, It ain't working for me" was the equivalent of my drowning her baby in a bathtub. It was bad. She begged me to bring her here so we could talk about it. I'm a guy, we prefer having our fingernails pulled out, to "Talking" about shit like this. But she was unrelenting, and I caved, and sent an Uber. Maybe part of me was feeling like I deserved this "Talk".

I am downstairs as the Uber arrives, she gets out and it is obvious she has been crying. As men, we know we make women cry, but we really don't like to see it. Maybe because we have no idea how to make it stop. We go up to the apartment, and pull out the translator app. She goes on about how awesome we are together, etc., really making a full sales pitch. I toughen up and said "Sorry, no." I was expecting an avalanche of tears, but instead she said "Can we at least be friends?" My final dick move is coming now. "What kind of friends?" That's it, I'm a bonafide scumbag.

She reaches her hand up the leg of my shorts and grabs my dick. Part of me is thinking, she is still trying to make this work, but as my dick hardens, I decide that we are on the record as just being friends now, obviously she is okay with that! After the blowjob, I offer to drive my new "friend" home, as I often did. Uber can get sketchy later at night.

It's quiet in the car. I have my phone in the handhold on my car door, out of reach. I hear her start sniffling, and she grabs my hand and squeezes it real tight. She knows it's over. I'm driving as fast as I can, wishing now I had called her an Uber for this ride. I park in front of her apartment. As I always did, I came around to open her door, and she threw herself at me. Crying and holding on for dear life. I let her get some of it out, and finally pried her loose. She stood on the sidewalk, sobbing. I could see her in my rear-view mirror, until I turned the corner. That was tough.

My first thought, as I pulled out of her complex on Sheldon Road, for my 25 minute drive back, was relief. Thankful "that" was over. I drove on, thinking about what I had done to this woman. She did not deserve that. I was a truly shitty person, who probably deserved to be alone. Even though she was obviously my rebound girl, I still vowed to myself on that drive home, that I would never do that to another person again.

Ashley popped up on Match one Sunday morning. I was on my balcony, drinking a coffee, and looking at downtown from 20 floors up. It is a good time to scan the dating sites... quiet.

We had chatted, moved to text, had a short, but good, first meeting and then when out to dinner a few days later, and had a nice time. I had put Ashley in the "strong prospect" category. As far as I am concerned, if things are not moving forward, they are moving backward, so I decide to try to setup a third date with Ashley.

"What are you doing this weekend?" I text. "You!" she replies. Yup, that was Ashley, a little bit of a jokester. But I like it. "Friday night?" I text. "Any night!" she replies. It seems our second date must have gone even better than I remember. "Lol, How about Malio's at 7?" I text. "Perfect, this time I will take an Uber, see you then 😘." she replies.

Uber is awesome. It has probably prevented untold numbers of DUIs, and most likely some deaths as a result. As a guy, what I hear, when a girls says "I'm Ubering to you.", is that she won't have a car to deal with. It is the ultimate in flexibility. If a woman is going to drive her car to meet you downtown, it creates a several challenges. First she has to park, or valet it somewhere. At the end of dinner, her car is hanging out there like a boat anchor. If we decide to maybe go back to my apartment, it's even more work. "You can ride with me." The valet brings her car up, she gets in and reaches over to unlock the passenger door for me, realizing her car is a shithole. "Sorry, my car is dirty" says every woman whose car any man ever got into, because they are always shitholes. My apartment is in one of the three high-rises on Harbour Island, a short drive from anywhere in downtown, Ybor or South Tampa. I'll direct her to the garage in my building, where visitors can park, some kind of empty food bag crunching on the floorboard under my feet.

I'm sitting at the bar at Malio's sipping my Manhattan at 6:45, considering whether I should wait for Ashley to come in here, or if I should go meet her at the valet stand, where Uber will drop her. As much as I really enjoy watching a woman enter a place scanning for me, this is our third date. I'll slug the drink, and walk out to meet her.

As I approach the Valet stand, I see an Uber pulling away, and Ashley is standing there... 5 minutes early. She looks stunning. She's wearing a much slinkier dress than our first two meetings, and I take that as a good sign. I reach her and go to give her a hug. I guess she was expecting a kiss, as I felt her lips graze my cheek as my head moved to the side of hers. I pull my head back quickly and give her a quick kiss. Damn, now I remember giving her a kiss goodbye on our second date, which should clearly be the proper "Hello" on the next one... but she seems fine.

I grab her hand and we start walking up the walkway back to Malio's which is at the back of the "Beer Can" building. "How was the ride?" I asked. "Well, the guy adjusted his mirror to be looking at me the whole way, but it was fine." she replied. Ashley has one of those bodies that looks like it was combined from two slightly different sized women. From her head to her waist, and her feet to her thighs, she's a size four, but her hips and butt are a size 6. I let go of her hand, and motion for her to keep walking. She smiles over her shoulder and complies, knowing exactly what I am looking at. We reach the door to the office building lobby, and when I pull it open a gush of wind from pressure blows her hair and her dress. Damn she looks hot.

"Reservation for Steve." I say to the hostess. "Yes, right this way." says the hostess, who turns and starts walking. We follow her as she goes through the lower lever, and up to the upper deck, and starts moving towards a table opposite of the view. "I think we'll sit here." I said, motioning to a four-top with an great view. I detect a slight annoyance, but I don't give a shit. "Of course sir." the hostess says as she collects the menus off the shitty table she was trying to put us at. I never understood this effort to seat people at the worst available tables first. Why is the person behind me going to be any better? We take our seats facing out to the river, with our backs to the restaurant. Not normally a position I like, but it somehow works, and feels almost like we are alone.

"Can I start you guys with some drinks?" says the waitress, interrupting the beginning of our conversation. "You go first." says Ashley. "I'll have a Woodford Manhattan." I tell the waitress. Ashley looks at me and says to the waitress "Same." without looking away from me. She is pretty fucking awesome.

Ashley is beautiful and sexy, but she's no dummy... far from it. If that was all she was, we would not be on a third date. I've had sex with beautiful, but vapid, women before... it is not very satisfying. I have not slept with Ashley yet, and may not this evening either... but I'm in no hurry. The dinner conversation is stimulating, and even though she is showing a fair bit of cleavage, my eyes stay on hers as we talk. Dinner is wonderful.

After signing the check, I say "Shall I call you an Uber?" I'm thinking, Please don't say yes! "What do I look like? Cinderella?" she says... and I am thinking she kind of does. "Okay, how about we walk off that dinner on the Riverwalk?" I suggest. "Perfect" she says. How nice is it that neither of us has a car to deal with. We get up from the table and turn, and the restaurant is packed, and suddenly it seems very loud. I had not noticed the noise level before. We head out.

"Right or Left?" I say as we reach the Riverwalk. "Your place is left right?" she says. I'm thinking... so it is.. and grab her hand and we make a left. The Riverwalk in Tampa is really a jewel of the city in my book, especially at night. We are walking silently for quite a while, I am wondering what she is thinking, as we reach the Sail Pavilion. "Do you want another drink, or water?" I ask. "Is that Jackson's?" she says, looking across the channel at Harbour Island. I lean in close to her and point my outstretched arm down her line of sight "That's Jackson's there, and that's America Social next to it." "Let's go that way." she says, and starts walking, pulling me by my hand.

A few minutes later, we are at the peak of the Harbour Island bridge, we can already hear the people sounds from the clubs, and she stops "Which building is yours?" "That one." I say, again pointing like you might, if you where showing a kid a particular star in the sky. "Do you have drinks there?" she says, smiling. "As a matter of fact..." I reply, and she grabs my hand and starts pulling me to walk again. We go right past the crowded clubs, and continue the few blocks to my building.

"Welcome back Mr. Steve." says Carlos, from his desk in the lobby as we enter. "Thanks Carlos, this is Ashley." I say, as I slowly continue past him towards the elevator bank. "Nice to meet you Miss Ashley." he says. She smiles at him, possibly wondering how many women Carlos has been introduced to. The middle elevator opens, a woman with two small yipping dogs comes out, and we replace her. I press "20".

My apartment is very nice. As we enter I say, "Alexa, I'm home!" Alexa runs my pre-programmed routine in the dark, turning on certain lights to certain levels and starts playing smooth jazz. Ashley looks at me, her brow slightly furrowed, and says "Really?" "Hey, I'm kind of a tech nerd." I say. I give her the quick tour, my 2nd bedroom that is an office, the master bedroom, and end with the balcony. This night, Tampa did not disappoint, the view of downtown is spectacular. "What would you like to drink?" I ask, as she sits in one of my Adirondack chairs on the balcony. "Can you make a Manhattan as good as Malio's?" she asks. "Better" I say and head to my bar.

Five minutes later, which felt like a very long time, I was pushing the balcony door open with my hip, as I brought out two Manhattans in Martini glasses. She took a sip, and smiled. I asked "Better?" She responded, "Yup, I'm thinking maybe we call Uber in the morning." "Yup." I smile.

I had been eager to see Susanna again. Our first "meeting" was after work on a Tuesday, at Boca in Brandon. She works downtown, and offered to go home, "freshen up" and come back to downtown, and tempting as it was to not have to drive to Brandon, accepting that seemed like a dick move. So I picked Boca, because it was near her. That first meeting went very well, so I asked for a second "date" and she agreed to dinner on the upcoming Friday.

I'm a fan of Ocean Prime at International Mall. The food and cocktails are great. If you just show up at the bar, you would be lucky to get a table, and probably have to wait for a high top. I prefer the bar, because it has a piano player. The trick is to make the reservation on Open Table a few days in advance. The restaurant always calls to confirm, and that's when I say I want a booth in the bar. So far ,they have always accommodated. The booths are fairly large, semi-circular facing the bar, which makes for fun people-watching. Even though they can probably fit six people, I have never had an issue getting one for two. All set for Friday at 7:00 PM.

Friday, 5:00 PM "We still good?" I text her. "Absolutely, on my way home to get ready, I'm looking forward to seeing you again ☺️ ☺️ ☺️ ." she replies. I always like to arrive early for my solo Manhattan, so I shower up and start to get ready myself. She will drive herself there. It's our first "real" date, we don't know each other yet. If I were a woman, I would never get in a car with a man, until at least the fourth or fifth date, so I do not offer to pick her up.

Friday, 5:45 PM "Hey, I hate to do this last minute, but I am feeling depressed and I won't be going out tonight." she texts. Umm...weird, she was three smileys happy 45 minutes ago. But whatever, "Okay, some other time then?" I reply, as though I am not annoyed at all. I get no response.

Friday, 6:00 PM. Now what? All I was missing was the spritz of YSL, and I was going to be heading out the door! I think for a second, remembering how I hated the bar scene by myself. How much worse would that be, sitting by myself in a six person booth? Fuck it, I'll just walk down the block to Cafe Dufrain. It has a decent vibe, mostly locals; Melissa the bartender is nice, and she can make a decent Manhattan.

Saturday Noonish. "I am soooo sorry, I just had some issues last night, and I would not have been good company." she texts. I'm still a little confused, but our first meeting seemed to go so well... "No worries... I understand." I reply, even though I don't understand at all. "Try again?" she texts. Hmm, well I am not chancing another Friday night with this one, until I figure out what is going on. "How about lunch downtown Monday?" I respond, knowing she works downtown, and it would only require a scooter ride on my part to get there. "Perfect" she texts. I reply "Say 11:45, you pick a place near you?" No reply.

Monday, 9:00 AM. "Are we still on for lunch?" I text. She responds, "Absolutely, see you there!". Umm, "Where?" I reply. "Lol, how about Freshen, it's easy?" she responds. "Okay, see you at 11:45" I text. "Let me know when you're almost there, and I'll come down." she says. I'm thinking, I will fucking be there at 11:45, but I reply, "Okay 👍"

Monday, 11:35 AM. "Hey I'm almost there." I text, even though I was already there, because I am always early. "Okay, I just have to finish a couple of more papers and I'll be right there." She responds. Huh?

Monday, Noon. "I'm on my way" she texts. No explanation or apology for knowing I have been standing there, for what she thinks is 15 minutes, but was actually 25.

I see her walking down the street towards me and she waves. I wave back, and a minute later she is saying, "I was trying to get a few things done before the holiday." "Oh cool, so you are off now?" I say. "I will probably go back after lunch, I don't really have anything pressing." she says. I'm thinking, but getting some papers done while I was waiting was urgent?

I am noticing that she is not as pretty as I remember... I obviously did not get my Manhattan. I think I am just annoyed with the whole thing. She clearly has some issues, or loose screws. I suspected that, before I came to lunch. So I am now seeing her without my rose colored glasses. Getting through lunch felt like a chore, but I'm not the guy who is just going to walk out, and leave her sitting there. However, it's obvious that this path has come to an end.

Lunch concludes. I can't remember now, what she even talked about. "So, we should do this again." she says with a smile. I say, "Yes...maybe..." as I give her a real-life thumbs-up, and start looking for a scooter to ride back to my apartment. It starts to rain.

"You make a great Manhattan." I say to the bartender, when he stops back by to ask how it is.

I recently started drinking Manhattans. It is a classic drink from way back. I discovered them this past Thanksgiving. Single now, I was asked to join my brother at my parents townhouse for dinner. My brother has been single his whole life, and has never had anything to do, other than to dote on my parents. I have always had to "fit" them into my otherwise busy family schedules, but not him... and he's a martyr about it. When I asked what I could bring, he said "nothing, I have it all covered". What a dick. But I'm not going empty-handed, and I recall my parents enjoying those classic cocktails. For Mom it was the Sidecar, and for dad... always the Manhattan. So I hit the liquor store, with my internet found recipes, to buy the necessary ingredients. Not to be completely overshadowed by my brother, I drop about $250 on high quality stuff and head over.

Dad is in rough shape, glued to a recliner, with an oxygen tank and a TV remote. He asked me once if there was something other than Netflix... because he had seen all of it. Mom looks at my armload of liquor with surprise, and my brother shakes his head and frowns. "He can't drink Steve." he says, trying to take any wind out of my sails. From the other room my Dad says, "Sure I can, it can't do any more damage." I give my brother a grin, and start following the recipes. 30 minutes later, I hand my Mom her Sidecar, and bring my Dad his Manhattan, partially blocking his view of the TV. He takes a sip, and let's out a huge smile. I have not seen him smile in a long time. I'm thinking to myself, "Fuck you brother". Then Dad hands it back to me "That was great, thanks" — Great! You took one sip. — "You can finish it" he says. So I do, and now it is my favorite drink. Dad died a week later.

It's 7:30, Thursday night at CW's Gin Joint in Downtown Tampa. This place is always crowded. I am sitting at the bar with my foot on the stool next to me, as if to say, "Don't even think about taking this chair." We were supposed to meet at 8, but I always arrive early. I enjoy my solitary Manhattan time, but just one. Drunk on a first meeting seems like a bad plan. I always find a spot where I can clearly see the front door. There is something about watching a woman, dressed to the nines, first walking in. Her face a combination of nervousness and hope, as she scans for a man who she has only seen in photos.

We are meeting for "Drinks", but of course I have a dinner reservation for 8:30 setup, in case things go well. The clock ticks 8, and as if she had been waiting outside for that exact moment, the door opens and she enters. Wow... she's the opposite of a catfish... she looks even better than her photos. I am nervous for a second that she might be out of my league... but I've never lacked confidence, and the concern passes, as I wave from my seat. Both of our profiles listed us a 5'-8", but she is wearing 4" heels, which becomes obvious when she reaches me at the bar. I don't mind a bit.

"Steve?" she says, a slight questioning in her voice. I look exactly like my profile, so I am not sure if I am detecting disappointment... but I mirror the motion, "Sarah?" "Yes!" she says, and moves in to give me a hug as I stand. I'm not sure why, but a hug seems so much more optimistic than a handshake.

"Have you been waiting long?" she says, as she drapes a sweater over her stool and slides onto it. Not wanting to seem too eager I say, "I got here just before you". She eyes my almost empty Manhattan, and obviously knows better.

We had been chatting for a few days prior, so we had already covered some of the basics. I wave the bartender over, "What can I get you miss?" he says to her. She replies, "I'll have what he's having." It does not make any sense, but for some reason, I am extremely pleased with this answer. She does not even know what it is. I'm not sure if it was the Manhattan I already had, or not, but it suddenly feels warmer in here.

First meetings are kind of like dancing with someone the first time. You step on each other's toes as you find the rhythm. When things are clicking, it does not take long to get in sync, when they are not, that sync never happens. She is wearing the perfect dress for this. Not too short or tight, but enough for you to see what her body may look like. It is not the most important thing to me, I am pretty open to different body types... within limits. Still, I take the opportunity to look her over, as she is looking the place over facing away from me. I am a man after all. Her drink arrives.

"Cheers!" — she says holding her glass up towards me. I pick mine up to move it towards her's and she stops me, — "It is bad luck to cheers without looking into each other's eyes". I look up, above the rim of our almost touching glasses, and meet her gaze. "Cheers!" I say, and we clink glasses. I am not sure how long I should hold this gaze, but I decide I will let her break it first. Several seconds go by, then she smiles and takes a sip, still not breaking the gaze. I turn my head back towards the bar, losing this round. I am a little flummoxed, this is feeling a lot more intense than a first meeting normally does ten minutes in.

I don't want to lower the heat, but I don't want to assume the heat is elevated either. I don't even know her yet, and could easily be misreading things. "So, where did you go on your last vacation?" I say, knowing that question usually leads to some conversation.

"Bahamas" — she says — "with my ex." I am hoping this is not the start of hearing about her ex from now on. I get it... it was the last person you cared about. Mentioning them here and there is fine, but too much... says you may not be over them. I have already had my "rebound" girl, and I prefer not to be someone else's "rebound" guy. It's a shitty spot to be in.

It's a little awkward now, I don't want to extend that line of conversation, because I obviously don't want to have the ex become the focus. "But I don't want to talk about that." she says, and I'm relieved.

You can't help yourself. If things are going well, even on a first meeting, you kind of let your mind wander with what-ifs. You start picturing what life might look like, if she became a part of it. I'm picturing Sarah now, with me, in the Bahamas. It's not a bad picture, but I don't even know her yet. She has a professional job, and seems to have her shit together, and my mind starts assembling the pieces of who I think she is, when she interrupts "Are you hungry?"

"I'm starving!" I say, as I give a thumbs up to the hostess from behind her back. "Me too!" she says, as the hostess arrives and says "I can take you to your table now." Sarah looks at me, with one eyebrow raised "Just drinks huh?" I smile and shrug, as we make our way to the table I had previously requested in the corner. I slide into the seat in the corner facing out, as she takes the seat to my right. It is a little trick I learned. Nobody wants to sit with their back to the restaurant, and by taking the corner seat, she will naturally sit next to me, on one side or the other, instead of across from me. But I get the feeling she would have either way.

"Here's the menu, specials are on the first page insert, can I freshen your drinks?" says the waitress. I look up... damn she waited on me for my last "first meeting" here. I hope she doesn't say... right as she says "Welcome back sir." crap. "Come here often?", Sarah says, and I act like I did not hear her, "Yes, two more of these I say, looking at her for approval" She nods, and the waitress turns towards the bar and scurries off.

Appetizers can be an interesting test, "Do you like Escargot... or Calamari?" I ask. "Either, or both." she says, clearly not intimidated by them. I look around the restaurant and notice a few guys checking her out. I smile at one, who is looking a little too long, and he moves his gaze upwards, as though he was just looking around. It does not bother me. What would bother me, would be if she was looking around at others, but she's not. I bring my eyes back around to hers, and she is looking into them. I am wondering if she is also processing some "what-if" thoughts.

"We'll have the Calamari and the Escargot to start." I say to the waitress who has returned with our Manhattan refills. Manhattans are strong... I know that two is my limit, and I wonder what her limit is. We gaze into each other's eyes, and clink again, "Cheers!" we both say in unison.

We devoured the appetizers, she was not even pretending to not be hungry. I ordered a big steak, and she ordered some fish thing that was on the specials page. Conversation was easy, we found a rhythm pretty quick. Not content to wait for me, she motions to the waitress, waves a finger over our glasses, and signals for two more. This is about to get interesting. Ordinarily I would be switching to beer now, and I have no idea what her limit is. She is clearly feeling it, as am I, she got quite giggly over the last hour.

The food arrives to our table of gigglers, and I'm not even hungry. I do that all the time... order a big meal, and then have two bites of it. Maybe it was the appetizers, or maybe it was the Manhattans, who knows. She seems to be in the same boat, but eats a little more than I do. The alcohol is kicking in and we are mellowing out now, giggles replaced with sultry looks. I am not trying to give a sultry look, it's just how I look when I've had too much to drink... not sure about her though. "Are we done?" the waitress breaks the sultry silence. "Ummm,", I look at Sarah, who nods. "Want any boxes?" the waitress asks, looking at the mostly full plates. I look at Sarah again, she shakes her head, the table is cleared, and the waitress vaporizes.

I am looking at our almost empty "third" Manhattans. I definitely don't want another one, as I am sure I will embarrass myself. "Care to see our dessert cart?" — the waitress is back — "or a refill on your drinks?" Please, please, please.. "No" Sarah says, we're good. Whew, I ask for the check.

It's almost 11 PM, the night has flown by, as I realize I am sitting with a woman who has had too much to drink and drive. Hell, so have I. It's not that far a walk to our individual places, but I would have to escort her to her's first, so that would be a long walk for me. "What do you want to do now?" she asks. I was already thinking that this first meeting, had turned into something a lot longer than I had anticipated. I like her, and I am buzzed, so I don't want to screw it up now.

"We should probably call it a night," — I say — "we both have work tomorrow." hoping logic would kick in. "You can come over to my place," — she says with a hint of a slur — "or we can go to yours... they're same distance." Okay, I'm a guy, and like all guys, I am hard-wired for sex at the drop of a hat. I'm looking at her, knowing it would probably be pretty awesome too. But... I'm not that guy. It's not that I have never had sex on a first meeting, but not when she is clearly buzzed. I'm pretty sure that's called rape, even if she does not regret it the next morning.

I feel a hand on my leg, moving upwards under the table. I don't know, or even care if anyone can see. I'm also buzzed. She reaches my dick, and gives it a squeeze. I look at her, and see her tongue pushed slightly out of the corner of her smiling mouth. "Let me call you an Uber." I very reluctantly say.

I'm flipping through channels on a quiet Tuesday evening. "Hi Steve, it's Me! 😀" appears on my phone's text notifications. I open the app. Who the fuck is "Me". I don't want to be rude, but the last time I thought I could deduce who was texting me I said, "Back from your trip already?", and she said "What trip?". I am thinking that I will just stay neutral... chat about weather or something to see if she gives me a clue. But then, how awkward would it be to still not know after like two days... and then have to ask...

"Hi! Who is this?" [sent] Better not to risk it.

"It's me silly. You suggested we move to text a couple of days ago..." [received] Not helpful, a couple of days in the dating apps, is like a week in real time.

"Sorry, I have a short memory 😀 Give me a hint?" [sent] I'm hoping I don't annoy her, but I really need to know who she is.

"From Bumble..." [received] Great, now I have to go into that App and try to figure out who this is. I open Bumble and jump to the conversations tab... I see that she could be one of two. Ugh. I decide I will have to take a risk.

"Play any racquetball 🎾 this weekend?" [sent] Fingers crossed.

"No" [received] Did that mean she did not play, or she did not know what I was talking about?

"I have not done that in a while ☹️" [received] Whew, okay now I know who this is. I edit her name to "Tonya from Bumble", and go back to look at her photos again. Damn, she deleted her account, I just looked at it a minute ago, but I remember her being cute.

"What part of town are you in? I'm downtown" [sent] When I first started, I found myself in a great conversation with a girl who lived in Atlanta. I was thinking about flying up there to meet her, but then thought, how is this going to work? So I tightened up my radius to at least women I could get to... ideally in less than 20 minutes.

"I told you silly... I live on Davis Island 🤷‍♀️" [received] I am wondering if it is unusual to be having multiple conversations going on, I assumed women did also... or are they just that much better at remembering details?

"Cool! I am actually on the next island, Harbour Island" [sent]

"I know, we had this discussion... how many women are you talking to?" [received] Uhoh, this is probably not a good question.

"A few. I see you deleted your Bumble account" [sent] Maybe I can divert the conversation, because if asked specifically, I would have to tell the truth, which means I would have to go and actually count them.

"Yes, I usually only pop on there for a day or two at a time. I met you, and decided to give it a rest." [received] I am wondering how much should I read into that... but it sounds positive.

"I went back to look at your profile again, but it was gone 😦" [sent]

[incoming photo] Ah yes..... I remember her now.

"Oh yes, the cute one 😉. Since we are so close, we should meet for coffee one morning ☕" [sent] I have been down the road of a few long text conversations. Everything can seem great, then you meet, and it's just not there. I hate even thinking that having a nice conversation could end up being a "waste of our time", but the reality is, that it could well be.

"Or drinks 🍸 LOL" [received] First meetings are a critical pivot. Some women like to play it very safe, like coffee with a fixed end time since they have to go to work. I get it. I mean if things are not sparking, it sucks to have committed to a whole evening. "Drinks" is a little more aggressive than coffee, and I read that as a sign of higher interest... or she could just be an alcoholic.

"Great! How about Thursday?" [sent]

"Do you have plans for Friday yet?" [received] I usually avoid have a first meeting (I don't even call those dates) on weekends. Even if I don't have plans, it just feels like more of a commitment than "Drinks on Thursday".

"Nope, no plans. How about Jackson's?" [sent] I am not crazy about Jackson's, but it's close to both of us. Plus, if things are going well, it's easy to roll right into dinner.

"What time?" [received] Let me see. It's a Friday, which means she works, and may not get home before 6, and I am sure she will want time to put herself together. But it's close by.

"How about 7:30?" [sent] That should give her enough time.

"How about 6:30?" [received] Why ask me if you already have a time you want?

"Sounds good! I'll meet you at the outside bar at Jackson's this Friday at 6:30 😀" [sent] I learned to be very clear on the details. I won't tell her, but I will get a dinner reservation for 7:30... just in case.

"Perfect, I'll see you then. And BTW, I am kidfree all weekend 💋" [received] WTF?

I have not been out here very long; the dating scene that is. Obviously, being a rookie, I signed up for all the dating apps. I was remembering my grandfathers' motto about prescription pills... "If one is good, then three are better". He died young.

Across the dating apps, you see many of the same women, who are also exploring their app options. My friends warned me not to sign up for Tinder, so of course, I immediately signed up for it. It's definitely shady around the edges, but they are all pretty much the same... photos and limited information.

I'm not sure what you can tell about a woman from a few photos and bullet points. But you do start to learn how the "system" functions. Step one, I start "liking" a few profiles. A couple of days go by... nothing is happening. Maybe I am not doing it right, and my "likes" are not going through. I mean, I know I am a good catch. I try "liking" a few more... nothing... not even any views. This is starting to feel like a waste of time. Maybe "likes" are not enough, I add a message, "Hi!". There we go, now I am getting a few views... but no replies. I actually read the complete profile, or at least what is provided, which sometimes is not much. I decide to send a longer message, "Hi Claire, I also enjoy bike riding!" Bingo. "Hi Steve, where do you ride?"

Someone should write a tutorial for women on how to create their profiles. A single profile photo consisting of a flower, may have some important meaning, but as a guy, the meaning is lost on me. Photos of you lying in bed, or in skimpy outfits will probably get you a lot of attention, we all know men are visual beings, but I don't think most women are seeking the kind of guy who only responds to that. It feels... desperate. There is also some irony in posting a suggestive photo, and then saying "No Hook-ups". We are but men, and just not that smart.

Bullshit! Profiles are mostly bullshit. Photos from high school, weird angles, filters on every photo or no pictures of you standing. The only people who like photos of women with cutesy filters... are other women. As a guy, I don't need 20 photos either. If I see 20 photos, there is going to be one you wanted to share, maybe because it was taken at a hip place, but where you just don't look your best. I will assume you probably look no better than your worst photo. I'm not bothered by photos where your ex is cut off, it shows how you looked when you were happy with a man. Four photos is plenty, provided they are recent. Neither of us benefits from seeing how you used to look.... it's not like that is coming back.

Women seem to be more honest in their words, than their photos. Still, turnoffs for me, and I assume for most men, are statements like: "Trying this again", "My friend put me up to this", "Don't waste my time", "No Hookups", "Seeking marriage minded only", "I'll fill this in later", "Seeking that special someone (puke)". I also don't really need a detailed breakdown of who you are looking for, my profiles' job is to provide a start on that. What your detailed description of your ideal man does give us, are things we can say to you, that we know you want to hear, true or not. I would prefer to read about who you are, rather than who I should be.

Women also tend to be very specific. Height 5'-10 to 6'. Really? 2" is your full acceptable range? At the end of the day, tall/short, skinny/heavy, old/young, etc. will all be eclipsed in significance by "real" chemistry. I recently learned a new term, "sapiosexual" which is a person who finds intelligence sexually attractive or arousing.

Back to "Hi Steve!". Am I the only one who is tiring of the monotonous first dance steps?

Her, Morning: "Hi Steve!" Me, Late Afternoon: "Hi Alexis, how are you today?" Her, Midnight: "Great, how was your day?" Me, Next Afternoon: "Not bad. You got any fun plans for the weekend?" Her, 1 AM: "I might go to the beach with friends." Me, Next Morning: "Sounds like fun." Her, Next Morning: "Yes." Me, Mid-Afternoon: "I hear it may rain this weekend." Her, Midnight: "Noooo :(" Me, Early Afternoon: "We have been talking for four days now, do you mind if we move this fascinating conversation to text?"