Dating Intentionally

What if dating apps aren’t the problem, but the expectations we bring to them? In this episode, I’m talking with sociologist and dating expert Dr. Jess Carbino about how dating apps have changed the way we meet people, why we put so much pressure on finding an instant connection, and how to approach dating with more intention.

Jess shares what she learned from her time as Tinder’s 25th employee, why the spark isn’t the only thing that matters when choosing a partner, and how romantic relationships can help us understand ourselves and change the patterns we bring into our relationships.

We’re getting into how to...

• Use dating apps as a way to meet people instead of treating every match like a promise of a relationship
• Let go of the pressure to find a magical meet-cute or experience love at first sight
• Balance chemistry and attraction with compatibility and long-term potential
• Understand how our early relationships shape the patterns we repeat in adulthood
• Think critically about how AI can help with dating and where it can get in the way of genuine connection
• Decide what matters most to you before you start swiping
• Know what you can and can’t learn about someone from a dating profile
• Create a dating profile that reflects who you really are instead of who you think you should be
• Stop trying to present an idealized version of yourself to attract a partner
• Approach dating with more confidence and trust that not meeting someone yet doesn’t mean you never will

Plus, Jess and I answer a dating dilemma from a 46-year-old single dad who has started dating a woman again after their first attempt ended because she didn’t feel the spark. We talk about how long to give the connection to develop, what might be holding her back, and what he should consider before continuing to invest in the relationship.

MENTIONED

Jess’s upcoming book: Better Love — available to preorder through her website

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What do you do when someone’s words say one thing, but their actions tell a different story?

In this episode, I’m answering four Dating Dilemmas about confusing behavior, mixed signals, and figuring out whether a connection is actually right for you. We’re talking about someone who keeps dating you but won't define the relationship, someone who says they’re ready to date but isn’t available, a long-distance connection that goes nowhere, and a relationship that starts intensely and then ends abruptly.

The common thread? Instead of trying to figure out exactly how someone feels about you, pay attention to how their behavior makes you feel and whether the relationship they’re offering is one you actually want.

Submit a dating dilemma: https://forms.gle/qNimkXbWPwM4euW47

In this episode:

• How to ask for clarity when someone avoids commitment
• What to do when someone isn’t ready to date
• How to navigate a confusing long-distance connection
• Why intense beginnings don’t guarantee lasting interest
• How to recognize unhealthy communication patterns
• Why you don’t have to match someone else’s pace
• How to move on without waiting for an apology
• When to stop playing detective and trust what you see

MENTIONED:

Episode 306 on pacing mismatch

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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 Playby 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:

• How long should you give someone to warm up physically when you’re tired of making the first move?
• What do you do when you’ve been telling little lies to make someone like you and now the relationship is getting more serious?
• Should you give a longtime friend a romantic chance when you’re not sure the attraction is there?
• 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. Francoabout 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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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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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”

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MENTIONED IN THIS EPISODE

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

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What can you learn from a first date that was just okay? And why does what happens after the date sometimes tell you more than the date itself? This is another episode of First Date Vibe Check, where I bring on a listener to walk me through a recent first date, from matching and messaging to the date itself, the post-date feelings, and what happened next.

This time, I’m talking to Katelyn (39), a single mom looking for a long-term relationship. She met “Trey” on Facebook Dating, moved the conversation over to Instagram, and eventually went on a two-hour dinner date.

We’re getting into:

• Why she prefers active first dates over dinner
• How she uses Instagram in her dating life
• The green flags she looks for in dating app conversations
• How she realized she wasn’t actually that excited about him
• Why feeling safe and having a “good enough” time doesn’t automatically mean you should go on a second date
• The post-date interaction that gave her a whole new data point
• Her firm boundary around second dates at home
• How she decides whether to give someone another chance
• And how to spend less time on the apps while getting to the date faster

Plus, Katelyn shares her best advice for staying positive when dating feels like a never-ending series of almosts.

MENTIONED IN THIS EPISODE:

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Whether you’re newly single, coming out of a long-term relationship, or you’ve simply been out of the dating world for years, getting back into dating can feel overwhelming. The apps have changed, the dating culture has changed, and you may have changed, too. In this episode, I’m breaking down how to get back into the dating scene with less pressure, more confidence, and a whole lot more perspective. Think of this as your dating bestie’s guide to getting your feet wet again without expecting yourself to immediately find your future spouse.

Listen for:

• How to know if you’re actually ready to date
• Why your first goal should simply be going on a date, not finding a relationship
• How to lower the stakes
• Why awkward, boring, or unsuccessful dates are actually part of the process
• The different ways to meet people to date
• How to manage fears around rejection, inexperience, being judged, or someone changing their mind
• Why you need to stop getting ahead of yourself
• How journaling, setting intentions, and finding ways to feel confident can make the process feel more manageable
• The biggest lessons I learned when I jumped back into dating after a six-year relationship

And I'm sharing a new dating dilemma at the end about trying to figure out whether someone wants kids before you date them.

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! https://www.bboutique.co/vibe/datingintentionally-pod

😎 Zenni: Get 15% off your first order and free shipping on orders over $65

🛏️ Boll & Branch: Get 15% off your first order

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