Dear Steve and Shirley, my roommate has ruined his relationship and mine. I’m in my late 20s and I have been roommates with my best friend since college. We both have steady girlfriends that are sorority sisters and we started dating them around the same time. I’m way more serious about my relationship than he is and I plan to propose to my girl soon. Marriage has not entered his mind and he still acts like he’s in college, messing with lots of other women on the side..............

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Dear Steve and Shirley, I am a young woman in my early 30s and I have been dating at 44 year old man for 10 years. We have had a great relationship until recently, when his mother moved to the city we live in. Since then, we’ve been fussing more and I’m really starting to dislike him. His true colors are showing, all because of his mother! We cannot move on with our lives because his mother is stuck on her son not being with her whenever he has extra time in his schedule...............

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Dear Steve and Shirley, I’m a 33 year old entrepreneur and I need your advice because Labor Day is coming soon. I live in a nice big neighborhood and I’m friends with everyone on my block. We’re a close-knit community and each year, we have a community outing for Labor Day at the neighborhood clubhouse. Last year, I took 2 big watermelons, ice and 2 cases of soda. Since I’m a bachelor, I’m not expected to do much more than that. We send around a checklist annually so we’ll know who’s bringing what, to the party.....................

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Dear Steve and Shirley, I’m a 40 something single female and my boyfriend is 69 years old. When we first started dating, he was my sugar daddy and he paid my mortgage, my car note, and sent me on vacation several times a year. But it wasn’t all of the money or the gifts that got me so hooked on him… it was the sex. This man is the best I’ve ever had and he does not need any enhancements to get aroused. We’ve been together for 5 years so I was shocked when he carelessly left his phone at home recently.............

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Dear Steve and Shirley, I’m a 35 year old man with 2 kids and a stepdaughter by my wife. I love my family, but I have come to a breaking point with my wife. For the second time in 4 years she has left the home and cut off all contact with me and the kids. The first time she left, she ran off with a man that she met online. She bought a bus ticket and rode out west and didn’t contact us for a month. Eventually, the guy dumped her and she reached out to me.............

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Dear Steve and Shirley, this isn’t a typical letter about cheating. I am in my mid 30s and I’ve been single for too long. I’m a nurse and I meet a lot of great men at work, but I'm not having any luck in love. When I meet a guy, I’m optimistic and not expecting him to play games just to have sex with me. I’m the type to text right back, return calls and show up early for a date. My girlfriends say I catch feelings too quick and I’m a hopeless romantic...............

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Dear Steve and Shirley, I’m a 37 year old single lady and I work with a married couple that gets on my last nerve. They’re the most happy couple in the world and they love to rub their relationship in everyone’s faces. We’ve all recently returned to the office and our boss let them share an office. They love to announce to everyone that they’re going to lunch and they walk around holding hands at all times and making flirty gestures when they’re around us...................

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Dear Steve and Shirley, I am best friends with the stupidest guy in the world. He’s been dating a woman for one year and he’s ready to give her the keys to the kingdom. He’s a successful realtor and he has a nice home and 2 cars. She has access to both cars and a key to the house. Before you think I’m jealous, I am married and this is my husband best friend that’s like family to us...........

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Dear Steve and Shirley, I’m married to a wonderful man that is 13 years older than I am. He is my everything and in the beginning of our marriage, we were very active and traveled a lot. Now it’s like he’s settled into being old and boring and I can barely get him to take a walk with me. I asked him if he was depressed and advised him to see a doctor. He went to the doctor and got a clean bill of health. We used to enjoy a martini in the evening to unwind and reconnect, but lately he’s turned to drinking brown liquor and I’ve noticed a change in him.................

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Dear Steve and Shirley, I need your advice because my daughter is in love with a country bumpkin. She is 24 years old and she got engaged recently and she brought her fiancé to town to meet my husband and I. As soon as they got out of the pickup truck, I thought WTH is this? He is a true country bumpkin. He has his GED because he dropped out of high school to work on his family’s farm. My daughter has a Master’s Degree and a promising career...............

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