Dating Intentionally

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:

Want to break down a first date with me on the pod? Apply here.

Get the Date Tracker app (iOS only for now) so you can do your own vibe checks!

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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! bboutique.co/vibe/datingintentionally-pod

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MORE FROM DATING INTENTIONALLY

Start tracking dates with Date Tracker (iOS)

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

If someone doesn't have any red flags, is that a green flag? This is the third episode of First Date Vibe Check, where I bring on listeners who are actively dating to walk through a recent first date with me, from how they met and planned the date to what actually happened and how they felt afterward.

This time, I'm talking to Jenny, a 27-year-old in the UK who is relatively new to dating and using it to build confidence, meet people, and figure out what she actually wants. She met "Steve" on Breeze, an app that skips the messaging and gets you straight to the date. We're getting into her unconventional first-date setup, the venue that had absolutely no vibe, the spontaneous bar-hopping that followed, and the green flags and amber flags she noticed along the way.

MENTIONED IN THIS EPISODE:

Want to break down a first date with me on the pod? Apply here.

Get the Date Tracker app so you can do your own vibe checks!

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

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.

How much information do you actually need before you make a decision in your dating life? In this episode, I’m answering four real dating dilemmas that all come down to that one question.

We’re talking about dating two people and not knowing who to choose, deciding whether a sexual-health disclosure is a deal breaker, trying to figure out whether a struggling relationship is still worth fighting for, and realizing in hindsight that someone wasn’t quite who you thought they were.

The common thread? You’re rarely going to get 100% certainty in early dating. Instead, you have to learn how to gather information, stay connected to your values, and make decisions based on what you actually know, not what you wish you knew.

Submit a dating dilemma

In this episode:

• How to choose between two people without turning dating into a competition
• What to do when someone discloses an STI and you’re unsure how you feel about it
• How to tell when someone is overwhelmed by life versus no longer prioritizing the relationship
• What to make of someone who seems great at first but gradually reveals a very different side of themselves
• Why you should evaluate people against your own needs, not against each other
• How to make good dating decisions without waiting for perfect certainty

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

Book a 1:1 with me

Slide into my DMs on IG

Watch the pod on YouTube

Reveal your dating blindspot (quiz)

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What if a first date is too easy and comfortable? This is the second episode of First Date Vibe Check, where I bring on listeners who are actively dating to walk through a recent first date with me, from how they met and planned the date to what actually happened and how they felt afterward.

This time, I'm talking to Carol Ann, a 47-year-old single mom in the Midwest who met Zach on Hinge after taking a several-month break from dating. We're getting into her dating-app approach, the messaging that led to this first date, and how she's learned to trust her body. Carol Ann also shares her thoughts on the spark, the green flags she noticed along the way, and what happened after. Stay tuned for her update at the end.

MENTIONED IN THIS EPISODE:

Want to break down a first date with me on the pod? Apply here.

Get the Date Tracker app so you can do your own vibe checks!

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

Submit a dating dilemma

Book a 1:1 with me

Slide into my DMs on IG

Watch the pod on YouTube

Reveal your dating blindspot (quiz)

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Why do so many relationships seem to fall apart at around three months? You finally feel like things are going somewhere, and then suddenly, something shifts. In this episode, I'm breaking down the “three-month cliff” and what’s really happening when a promising relationship suddenly fizzles, pulls back, or ends.

We’ll talk about:

• The 3 biggest reasons relationships fall apart around three months
• How to tell whether it’s a genuine incompatibility, a commitment issue, or simply a lack of chemistry
• Signs that it's you or them (depending on the situation)
• How to actually make it past the three-month mark
• Why a three-month relationship that ends is NOT a failure

Plus, I answer a dating dilemma from a 43-year-old man who is worried about eventually outliving his future partner.

MENTIONED IN THIS EPISODE

Episode 285 with Chris Rackliffe about codependency

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

Submit a dating dilemma

Reveal your dating blindspot (quiz)

Book a 1:1 with me

Slide into my DMs on IG

Watch the pod on YouTube

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This is the first episode of a new series called First Date Vibe Check, where I bring on listeners who are actively dating to walk through a recent first date with me - how they met, how the date got planned, what actually happened, and how they felt afterward.

First up is Savannah, a 30-year-old middle school teacher in California who's had a wild six months, including discovering the boyfriend she'd been dating for three months had a wife. We're discussing everything from why speed dating rebuilt her dating confidence to sending the first message when nobody reaches out to the exact moment a good first date starts to get awkward. Savannah also shares the shift that took the pressure off her first dates: you don't need to feel romantic feelings on date one; you just need to feel safe and curious.

MENTIONED IN THIS EPISODE:

Want to break down a first date with me on the pod? Apply here.

Get the Date Tracker app so you can do your own vibe checks!

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

Submit a dating dilemma

Book a 1:1 with me

Slide into my DMs on IG

Watch the pod on YouTube

Reveal your dating blindspot (quiz)

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

When you’re always the one texting first, planning the dates, and keeping a connection moving forward, it’s easy to start wondering: do they actually like me, or am I doing all the work?

In this episode, I’m breaking down the truth about effort in dating: why some people initiate more than others, what someone’s effort actually tells you about their interest, and how to stop spiraling when someone goes quiet.

Tune in for...

• What effort and initiation actually look like in dating (and why they matter)
• The real reasons someone might not initiate, and why the reason doesn’t change what you do next
• The one question to ask yourself when dating feels one-sided: do you want clarity, connection, or desire?
• The “I can’t tell” text and exactly when to send it
• Why “if they wanted to, they would” is complicated dating advice
• The difference between having standards, setting boundaries, and trying to control someone’s behavior
• Why initiation chicken and wanting to be chased can keep you stuck
• How multi-dating helped me stop investing in people who weren’t showing up
• How to tell the difference between a normal imbalance in effort and a connection that isn’t reciprocal

Whether you’re carrying a connection for a few weeks, wondering why you’re always the one making plans, or staring at your phone trying to figure out what their silence means, this episode will help you stop decoding their behavior and start paying attention to what their effort is showing you.

At the end, I tackle a dating dilemma from a man who reconnected with someone he dated 18 years ago and has spent two months texting without ever meeting up.

MENTIONED IN THIS EPISODE

Book a 1:1 with me

Close The Loop text templates

Free texting guide

THANKS TO OUR SPONSORS

💗 Bellesa: EVERYONE gets a free Rose suction toy with EVERY single order! 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

MORE FROM DATING INTENTIONALLY

Submit a dating dilemma

Slide into my DMs on IG

Watch the pod on YouTube

Get the Date Tracker app!

Reveal your dating blindspot (quiz)

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Do you tend to go all in when you like someone, to the point where you've lost touch with your own life a bit? I'm chatting with Chris Rackliffe, an anxious attachment coach and author of Needy No More: The Journey from Anxious to Secure Attachment, who's helped thousands of people heal from patterns of trauma, abandonment, and codependency. We're getting into why we lose ourselves in dating and what to do about it.

We cover:

• The earliest signs you're starting to abandon yourself when you meet someone new
• Why resentment is the clearest signal a compromise has tipped into self-betrayal
• Chris's framework for codependency
• Why guilt is proportional to how long you've been overriding your own needs
• His concept of emotional diversification, and why spreading out your sources of connection is a protective strategy, not just something nice to have
• How to apply this whether you're in early dating or an established relationship
• Whether opposite sleep schedules are actually a dealbreaker

At the end, we tackle a dating dilemma about whether opposite sleep schedules are a dealbreaker.

CONNECT WITH CHRIS

Find Chris on Instagram and TikTok

THANKS TO OUR SPONSORS

EVERYONE who signs up wins a FREE toy or gift card! bbvibes.com/DatingIntentionally

FREE STUFF

Dating Guides: 90 questions, FAQ, text templates & more

MORE FROM DATING INTENTIONALLY

Submit a dating dilemma

Slide into my DMs on IG

Watch the pod on YouTube

Join the Date Tracker app waitlist

Reveal your dating blindspot (quiz)

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Rejection doesn't have to destroy your confidence or convince you that you'll never find your person. In this episode, I'm sharing how to bounce back faster after getting rejected, ghosted, or hearing "there wasn't a spark." We'll talk about why rejection feels so personal, how to stop the anxiety spirals before they take over, and the mindset shifts that will help you keep your self-worth intact while continuing to date intentionally.

Tune in for...

• Why rejection feels so much bigger than it actually is
• How to stop telling yourself hopeless stories after a "no"
• The 24-hour rule for bouncing back faster
• Practical ways to stop anxiety spirals after rejection
• What to say when someone rejects you (and what not to say)
• Why rejection isn't a reflection of your worth
• The questions to ask yourself instead of "What's wrong with me?"
• My own experiences navigating rejection while dating

Whether you've been ghosted before a first date or rejected after a few months of dating, this episode will help you move forward with more confidence and resilience.

MENTIONED IN THIS EPISODE

• Dating Roadblock Quiz
• Episode 281 (Kelsey Darragh) on healing after heartbreak
• Episode 221 (Cole Zesinger) on moving on after a breakup
• My "closing the loop" text templates

Instead of asking "what's wrong with me," get curious and reflect on these questions:

• Am I consistently pursuing people who aren't available or aren't looking for the same thing?
• Am I showing up as myself, or am I trying to earn someone's approval?
• Am I choosing people based on mutual interest, or am I getting attached to potential before they've shown consistent effort?
• Am I overlooking signs that someone isn't able to meet me where I am?
• Am I being curious, showing interest, and being direct, or am I playing games to get their attention?
• Am I owning who I am, or leading with my insecurities?

THANKS TO OUR SPONSORS

EVERYONE who signs up wins a FREE toy or gift card! bbvibes.com/DatingIntentionally

FREE STUFF

Dating Guides: 90 questions, FAQ, text templates & more

CONNECT WITH ME

Submit a dating dilemma

Slide into my DMs on IG

Watch the pod on YouTube

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.