Dating Intentionally

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!
MORE FROM DATING INTENTIONALLY
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Take the quiz: What's holding you back in dating?
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Book a 1:1 with me
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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
MORE FROM DATING INTENTIONALLY
Date Tracker: Start your 7-day free trial! (iOS link)
Take the quiz: What's holding you back in dating?
Say hi on Instagram
Book a 1:1 with me
Submit a dating dilemma
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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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MORE FROM DATING INTENTIONALLY
Date Tracker: Start your 7-day free trial! (iOS link)
Take the quiz: What's holding you back in dating?
Say hi on Instagram
Book a 1:1 with me
Submit a dating dilemma
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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
THANKS TO OUR SPONSORS
😎 Zenni: Get 15% off your first order and free shipping on orders over $65
MORE FROM DATING INTENTIONALLY
Date Tracker: Start your 7-day free trial! (iOS link)
Take the quiz: What's holding you back in dating?
Say hi on Instagram
Submit a dating dilemma
Book a 1:1 with me
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.