Dating Intentionally

What if the secret to better dates isn’t saying the “right” thing, but worrying less about how you’re coming across and getting more curious about the person in front of you? In this episode, I’m talking with experimental social psychologist and author Vanessa Bohns about the science of what we say, what we hold back, and how other people actually respond to us.

Vanessa breaks down why we often underestimate how much people like us, why vulnerability tends to go over better than we expect, and how asking the right kinds of questions can create more intimacy without making a date feel like an interview.

We’re getting into how to...

• Decide when to share something vulnerable or sensitive in early dating
• Tell the difference between healthy vulnerability and trauma dumping
• Figure out why you feel the urge to disclose something
• Talk about your accomplishments without sounding like you’re bragging
• Understand the “liking gap” and why your dates may like you more than you think
• Ask questions that actually build connection instead of slipping into interview mode
• Use follow-up questions to naturally get into deeper conversations
• Handle dates where you’re doing all the asking and they aren’t asking anything back
• Decide whether you should give someone feedback after a date
• Be honest without saying something unnecessarily hurtful
• Stop focusing so much on impressing someone and start paying attention to whether you actually like them

Plus, Vanessa and I answer a dating dilemma from a listener who is four dates in with someone she likes and wondering whether she should proactively tell him she’s still dating other people.

MENTIONED

Vanessa's book: Should I Say Something?: The Science of What to Share―and What to Keep to Yourself

Vanessa's Instagram

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How do you actually know if you’re in a healthy relationship? In this episode, I’m breaking down the four pillars I believe healthy relationships are built on: responsiveness, safety, freedom, and connection. We’ll talk about what each one actually looks like, where we tend to get it wrong, and how you can start building these qualities from the very beginning of dating.

I'm getting into...

• What it really means to feel understood and cared for by your partner
• Why validation doesn’t mean agreeing with everything your partner says
• How to tell the difference between relationship safety and simply avoiding conflict
• Why calm and steadiness aren’t signs that something is missing
• How independence and freedom can actually strengthen your relationship
• Why your partner shouldn’t have to be your entire support system
• How small everyday “bids for connection” build intimacy over time
• What to look for in early dating if you want to build a healthy long-term relationship
• Four questions you can ask yourself to assess the health of your relationship

Plus, I answer a Dating Dilemma from a listener wondering whether she should give a promising connection more time or whether she’s already trying too hard to manage her way into compatibility.

MENTIONED:

Episode 244 on building inner security

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What if jealousy wasn’t a sign that something is wrong with you or your relationship, but an emotion you could actually learn from? In this episode, I’m talking with relationship coach Ally Iseman about why jealousy gets such a bad reputation, what it’s actually trying to tell us, and how to work through it without blaming your partner or shaming yourself.

Ally breaks down the different types of jealousy, including insecurity, comparison, fear of abandonment, distrust, and retroactive jealousy, and explains why learning to tolerate discomfort is one of the most important relationship skills you can build.

We’re getting into how to...

• The difference between jealousy and envy
• Figure out whether your jealousy is about you, your relationship, or something from your past
• What to do when jealousy comes up
• Work through retroactive jealousy
• Ask your partner for reassurance without making them responsible for your emotions
• Handle it when your partner is jealous of your past
• Understand the difference between boundaries, rules, and relationship agreements
• Stop trying to force certainty or commitment before you actually know someone
• Build the relationship skills that help you navigate uncomfortable conversations
• Decide what to do when the person you’re dating handles a situation in a way that completely turns you off

Plus, Ally and I answer a dating dilemma from a listener who showed up to a museum and caught the guy she was seeing on a date with another woman after he told her he was sick.

CONNECT WITH ALLY

on Instagram

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Dating comes with a lot of frustrating uncertainty. You can’t know if attraction will grow, whether someone will choose the relationship, or how another person will react when you tell them the truth. In this special 300th episode of Dating Intentionally, I’m answering your dating dilemmas about what happens when you want certainty, but the situation simply can’t give it to you yet.

We’re getting into four dating dilemmas:

1. How long should you give someone to warm up physically when you’re tired of making the first move?
2. What do you do when you’ve been telling little lies to make someone like you and now the relationship is getting more serious?
3. Should you give a longtime friend a romantic chance when you’re not sure the attraction is there?
4. How long do you wait when your partner says they need to “figure things out”?

I’m talking about...

• Why trying to control the outcome can actually make dating harder
• How to tell the difference between accepting someone’s pace and ignoring your own needs
• Why self-worth can affect how honestly you show up when you really like someone
• What to do when you’re curious about someone but don’t feel an immediate spark
• Why you don’t need to play out an entire relationship in your head before you’ve even gone on one date
• What “figuring things out” should actually look like inside a relationship
• How to make dating decisions when you have no idea how the story will end

And because this is episode 300, I’m ending with a rapid-fire Q&A covering questions like: What’s the most underrated green flag? How do you stop obsessing over someone after it ends? Should you give up if they cancel twice without rescheduling? How do you tell someone you don’t want to text all day? And how do you stay unbothered when you know the person you’re dating is seeing other people too?

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What if dating felt less like a stressful search for your person and more like an experience you could actually enjoy? In this episode, I’m talking with Serena Kerrigan, creator and author of Let’s Fucking Date, about lowering the stakes in dating, stopping the need to control the outcome, and staying open to connections that don’t look exactly how you expected.

Serena shares how meeting her boyfriend challenged her assumptions about age, success, and what the “right” partner should look like, plus the mindset shifts that helped her stop overmanaging her dating life and actually enjoy it.

We’re getting into how to...

• Use Serena’s “potential, practice, or plot” framework to make every date feel worthwhile
• Stop putting so much pressure on every first date to become something
• Stay open to people who don’t fit the picture you had in your head
• Tell the difference between showing interest and doing too much
• Give someone enough space to actually reveal how interested they are
• Let go of control when dating feels uncertain
• Get out of your comfort zone when your dating life feels stagnant
• Stop treating self-improvement like a formula that guarantees you a relationship
• Know when an “ick” is meaningful and when you might need to get a grip
• Date with a more abundant mindset when age and timelines are stressing you out

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Feel like you're done wasting time on the wrong connections? I get it! In this episode, I'm breaking down seven of the most common mistakes I see people make in early dating, from dating someone's potential and staying in situationships to taking constant dating breaks, avoiding uncomfortable conversations, and being pen pals. I'm also sharing what to do differently so you can protect your time and energy and get closer to the relationship you actually want.

In this episode, you'll learn:

• Why dating someone's potential can keep you invested way too long
• How staying in a situationship can delay you from finding your person
• Why constantly taking breaks from dating may be slowing you down and what to work on instead
• How speaking up about small issues early can reveal someone's ability to handle conflict
• What it means to date from your "back foot" and why it's a time waster
• Why texting for weeks before meeting can create false intimacy
• How to recognize red flags without confusing them with preferences
• Why getting curious about someone's behavior can help you make better decisions sooner
• How to stay grounded in who someone is today instead of who you hope they'll become

Plus, I answer a dating dilemma from a 40-year-old man who just learned that his new girlfriend occasionally smokes cigarettes and he's not sure what to do.

Ready to date with intention? Start your 7-day free trial of Date Tracker at thedatetracker.com! (iOS link)

MENTIONED IN THIS EPISODE

Ep 260 - How to end a situationship

Ep 186 - Tips for taking a dating break

Ep 286 - Balancing effort in early dating

Ep 192 - Sneaky red flags in early dating

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How much is your self-worth affecting the way you date? In this episode, I’m talking with psychologist and author Dr. Marisa G. Franco about how our past experiences can shape what we believe we deserve, how we interpret rejection, and even our ability to accept love from someone who genuinely likes us. We’ll also explore what it means to build self-worth and how to stop dating from a place of fear and start going after what you want.

We’re getting into how to...

• Understand the difference between self-esteem and self-worth
• Recognize when you’re dating to avoid rejection instead of pursuing what you want
• Understand why rejection hits some people so much harder than others
• Identify old experiences that may still be shaping how you see yourself
• Stop assuming someone doesn’t like you when there’s no evidence they don’t
• Build self-worth by paying attention and responding to your emotions
• Know when you’re seeking healthy reassurance versus outsourcing your worth to a partner
• Navigate dating when you don’t feel completely confident or worthy yet

MENTIONED IN THIS EPISODE

Worth: The New Science of Self-Esteem and Secure Attachment by Dr. Marisa G. Franco

Marisa's website

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MORE FROM DATING INTENTIONALLY

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There's a reason you keep dating the same people in different fonts: it's your dating patterns.

In this episode, I'm sharing the three patterns I discovered while tracking my own dating life, how they were getting in the way of the relationship I actually wanted, and what I did differently once I could finally see them. I'm also walking you through a simple way to identify your own patterns and turn them into experiments so you can start getting different dating results.

In this episode, you'll learn:

• What dating patterns actually are and how they can quietly influence who you choose and how you behave
• Common patterns like getting attached too quickly, chasing unavailable people, staying too long, or writing people off too soon
• The three dating patterns I discovered in my own dating life
• Why I stopped rushing physical intimacy and started approaching sex differently
• How I realized I was trying to earn affection instead of evaluating whether someone was right for me
• Why consistency can feel less exciting when you're used to chasing someone's attention
• How tracking my dates helped me spot behaviors I couldn't see in the moment
• How to turn your own dating patterns into small experiments that help you make different choices

Plus, I answer a dating dilemma from a 41-year-old man figuring out how to start dating again after a 13-year marriage—and how to avoid falling back into old people-pleasing habits.

Ready to date with more confidence? Start your 7-day free trial of Date Tracker! (iOS link)

MENTIONED IN THIS EPISODE

Episode 277 on IRL dating

What my date tracking note looked like & the emoji key

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How do you stay open-minded in dating without settling for less than what you want? And what happens when someone treats you well, checks a lot of the important boxes, but something still feels… off?

In this episode, I’m joined by licensed therapist Jordanne Sculler to talk about the messy, nuanced parts of dating that don’t fit neatly into a set of rules. We unpack why familiar relationship dynamics can feel more attractive than healthy ones, why self-awareness alone doesn’t always break old patterns, and how to tell when you’re honoring your needs versus shrinking yourself to keep someone around.

Listen for...

• How to be open in dating without lowering your standards
• Why dating checklists can get in the way of real connection
• The difference between self-soothing and suppressing a legitimate need
• Why someone healthy might initially feel uncomfortable or unfamiliar
• How to stop focusing so much on whether someone likes you and ask whether you like them
• What dating disappointment can bring up about your self-worth
• How social media can reinforce negative stories about dating
• Grieving the relationship or life timeline you thought you’d have by now
• Why processing disappointment is different from simply “getting over it”
• How Jordanne met her husband after initially writing him off

And at the end, we answer a dating dilemma from a woman wondering if she made a huge mistake by ending things with a great guy who didn’t feel like her person.

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MORE FROM DATING INTENTIONALLY

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In this episode, I'm sharing 5 tiny habits that can help you get better dating results, feel more confident and in control, and make dating a little more enjoyable. We’ll talk about how to make decisions without endlessly second-guessing yourself, learn from your dates, show interest without playing games, protect your mindset from dating negativity, and get clear on intentions early.

In this episode, we cover:

• How being more decisive can build confidence and self-trust
• Why tracking and reflecting on your dates can help you spot patterns and learn what actually works for you
• How to show interest when you're interested without playing it cool or worrying about “double texting”
• Why opting out of negative dating narratives can help you stay open and hopeful
• How bringing up your intentions early can help you avoid confusion, situationships, and wasted time
• Dating habits from the Dating Intentionally community that helped people stay grounded and keep going
• A dating dilemma about bad timing, competing connections, and whether being direct after two dates was “too much”

Ready to date with more confidence? Start your 7-day free trial of Date Tracker! (iOS link)

MENTIONED IN THIS EPISODE

Episode 286 - If they wanted to they would? The truth about effort in dating

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MORE FROM DATING INTENTIONALLY

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