Dating Intentionally

What if building a lasting relationship has less to do with falling in love and more to do with knowing yourself, choosing the right person, and learning how to love someone who is different from you? In this episode, I’m talking with relationship expert Kristy Scher about why we can’t rely on chemistry and the excitement of falling in love alone to build a lasting relationship, and how developing self-awareness and taking responsibility for our own behavior can change the way we show up in relationships.

Kristy breaks down the difference between falling in love and mature love, why disillusionment is a necessary part of building intimacy, and how learning to tolerate discomfort and embrace our differences can help us create deeper, more connected relationships.

We’re getting into how to...

• Find the right fit instead of getting swept up in the intensity of falling in love
• Understand the three essentials of a lasting partnership: love, lust, and like
• Move through disillusionment and build mature love
• Stay true to yourself while making room for your partner to be different
• Recognize how social media shapes our views of relationships and gender
• Understand how childhood experiences and personal wounds affect our relationships
• Take responsibility for your own behavior instead of focusing only on your partner’s flaws
• Appreciate your partner’s efforts while giving grace without dropping your standards
• Get comfortable with silence and stop feeling responsible for carrying every conversation
• Stop imagining a future with someone before you know them and learn to tolerate uncertainty in dating

Plus, Kristy and I answer a dating dilemma from a 26-year-old man who wants a serious relationship but finds himself imagining a future with women before he even knows them. We talk about why the desire for connection can make us rush ahead, how to get curious about our own unmet needs, and why taking the time to discover whether someone is actually right for you matters more than simply finding someone who’s available.

MENTIONED

Kristy’s year-long program: The Way of the Adored Woman™

Kristy’s Instagram

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Have you ever gone on what felt like a really good date, only to get the dreaded “I had a great time, but I didn’t feel a romantic connection” text afterward?

In this episode, I’m breaking down what actually creates romantic connection in early dating and 10 ways to make it easier for that connection to develop without forcing chemistry, performing, or trying to convince someone to like you.

I’m getting into...

• What a romantic connection actually feels like in the first few dates
• Why a great conversation doesn’t always translate into romantic chemistry
• Why first dates can feel more like performances than real connection
• The interview, audition, and evaluation date traps that keep dates feeling platonic
• Why playing it cool and waiting for the other person to make every move can kill momentum
• How compliments, vulnerability, and follow-up questions create more connection
• Why showing more of your personality makes you more attractive to the right people
• The role texting and between-date communication plays in building momentum
• Why physical touch and flirting matter and how to do both without making things overly sexual
• How being honest about your interest can make dating feel less confusing
• Why talking about your goals and dreams can create surprising intimacy
• How to give someone more access to the real you without oversharing
• Why your job isn’t to make someone like you, but to make it possible for them to actually get to know you

Plus, I answer a Dating Dilemma from a listener wondering how to embrace a slow burn when the person she’s dating is still seeing other people, including how to think about exclusivity, sex, and boundaries in early dating.

MENTIONED IN THIS EP

Ep 211 on flirting w/ Francesca Hogi

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What if getting divorced wasn’t the end of your love story, but a chance to rebuild your life and learn to date in a completely different way? In this episode, I’m talking with dating-after-divorce creator Alex Daly about dating after divorce, rebuilding your life from scratch, and how approaching dating with curiosity and an experimental mindset can help you figure out what you actually want.

Alex shares her experience of getting divorced in her late 30s, moving to a new city, and re-entering the dating world after a long break. We’re talking about her Hoe era, why dating doesn’t have to be so serious, and how letting go of the pressure to find a relationship can actually create space for a connection to develop naturally. We’re getting into how to...

• Rebuild your life and approach dating after divorce
• Use dating as an opportunity to explore what you actually want
• Have a "Hoe era" without shame, guilt, or putting pressure on yourself to find a relationship
• Date safely and have conversations about sexual health
• Handle ghosting and other disappointing parts of dating without taking them personally
• Let go of arbitrary dating rules and take an experimental approach instead
• Know when it’s time to try dating outside of your usual “type”
• Transition from enjoying your single life into a relationship without rushing it
• Have check-in conversations with a new partner without turning them into pressure-filled “what are we?” conversations
• Look at your own patterns and take responsibility for how you show up in relationships
• Talk about divorce in early dating without oversharing or bad-mouthing your ex
• Build a relationship differently after learning from what didn’t work in the past
• Trust that it’s never too late to start over, date, explore, or find love

Plus, Alex and I answer a dating dilemma from a listener who has spent years repeating a cycle with her ex-husband and continues to find herself attracted to men who don’t choose her.

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How fast should a relationship actually move? In this episode, I’m breaking down one of the trickiest parts of early dating: what to do when you and the person you’re dating aren’t moving at the same pace. We’ll talk about why pacing mismatches are so normal, how to tell when a relationship is simply moving slowly versus going nowhere, and how to navigate it when one person is ready for the next step before the other.

I'm getting into...

• Why there’s no universal timeline for becoming official, having sex, saying “I love you,” or hitting other relationship milestones
• The difference between a pacing mismatch and a pacing problem
• Why wanting the same relationship but moving at different speeds can still work
• How to talk about pacing without turning every date into a relationship check-in
• What to say when you need more time or when you’re the one waiting
• Why someone moving slowly doesn’t necessarily mean they’re less interested in you
• How to know when “slow” has become stagnant
• The five areas of a relationship where you should still see some forward motion
• Why catching feelings makes pacing feel so much more stressful
• How to stay present and keep vetting someone instead of obsessing over the next milestone

Plus, I answer a Dating Dilemma from a listener whose two past connections unexpectedly came back into her life.

MENTIONED:

The Slow Burn Masterclass: How To Stop Rushing Connections - live on 10/19!

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Why do so many couples who believe in equality still end up falling into traditional gender roles? I’m joined by Stefanie O’Connell Rodriguez, author of The Ambition Penalty, to talk about what happens when money, ambition, power, and gender collide in dating and relationships.

We get into why women’s success can create unexpected tension in heterosexual relationships, what happens when a woman earns more than her male partner, and why saying you want an equal relationship is very different from building one in practice. We also talk about dating when you’re financially successful, expanding what it means to “provide,” when to start talking about money, and how to think about a partner who isn’t where you want them to be financially.

In this episode...

• Why modern couples still fall into traditional gender roles
• What can happen when a woman earns more than her male partner
• Why believing in equality doesn’t automatically create an equal relationship
• What real support for an ambitious partner looks like in practice
• Why “providing” in a relationship should mean much more than money
• When and how to start talking about salary, debt, savings, and finances while dating
• How to date someone who is financially behind without dating their potential
• Why having a full life and strong community outside your relationship matters

MENTIONED

Stefanie’s Substack, Too Ambitious

Fair Play by Eve Rodsky

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Texting can create SO much unnecessary anxiety in early dating. You’re wondering if you’re texting too much, if you should text first, why they suddenly seem less responsive, or whether someone who’s great in person but terrible over text is actually worth pursuing.

In this episode, I’m breaking down what texting should actually look like before, after and between dates so you can stop analyzing every message and focus more on the connection happening in real life.

This episode originally aired in December 2023.

You’ll learn:

• Why texting too much before a first date can create false intimacy
• Why you don’t need to wait for someone else to text first after a good date
• The texting mistake that can turn a promising connection into a pen-pal situation
• What realistic communication between dates can look like
• What to do when you notice someone’s texting suddenly slow down or change
• How to handle dating someone who texts much less than you’d prefer
• Why double texting isn’t the dating crime people make it out to be
• What to do when texting turns sexual earlier than you’re comfortable with

Plus, I answer a new Dating Dilemma from a listener who's worried she accidentally gave her date the impression that she only wants something physical.

MENTIONED

Speaking in Thumbs by Mimi Winsberg

Free Texting Templates!

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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?

Submit a dating dilemma

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