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!
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
Submit a dating dilemma
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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
😎 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
Start tracking dates with Date Tracker (iOS)
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.

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.