156. The Best First Date Questions + What Daters Regret Not Asking Sooner

156. The Best First Date Questions + What Daters Regret Not Asking Sooner

Get 90+ questions to ask in early dating


Do you ever struggle with what to talk about on a date? Or maybe you want to get better at building real connections? In this episode, I’m sharing tons of inspiration for great questions to ask in early dating, the worst ones to avoid, and navigating tricky conversations without derailing the date. We’ll also dive into the number one topic that so many daters regret not bringing up sooner, how to answer "why are you single" (and what to ask instead). I also share how to ask better follow-up questions and scripts for handling tough topics like past relationships, STI talks, and career gaps.


Why they don't ask questions and how to deal


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Episoder(261)

254. Breadcrumbed by a Bartender, Boring Dates & Low Attraction (Dating Dilemmas)

254. Breadcrumbed by a Bartender, Boring Dates & Low Attraction (Dating Dilemmas)

In this episode, I'm answering four listener dating dilemmas, from deciding whether a "boring" but stable guy is worth more dates to navigating attraction when everything else aligns, to catching feel...

14 Apr 30min

253. How The Creator of Burned Haystack Method Found Love on Hinge w/ Dr. Jennie Young

253. How The Creator of Burned Haystack Method Found Love on Hinge w/ Dr. Jennie Young

I'm chatting with Dr. Jennie Young, creator of the Burned Haystack Dating Method and author of the brand-new book Burn the Haystack, on round two! This time, we're getting into everything from her own...

10 Apr 52min

252. How to Break Out Of The "Should I Stay Or Go?" Loop In Relationships

252. How to Break Out Of The "Should I Stay Or Go?" Loop In Relationships

I'm getting into relationship rumination and that "should I stay or should I go" loop that keeps you stuck without ever actually making a decision. I'm covering the science behind why your brain does ...

7 Apr 35min

251. What To Say In Conflict For Calmer Communication w/ Rikki Cloos

251. What To Say In Conflict For Calmer Communication w/ Rikki Cloos

I'm chatting with Rikki Cloos, the creator and author of Anxious Hearts Guide, one of the most grounded, accessible resources out there for healing insecure attachment. We're discussing communication ...

3 Apr 52min

250. Top 5 Ways To Show Interest In Someone (Even If You're Shy)

250. Top 5 Ways To Show Interest In Someone (Even If You're Shy)

In this episode, I'm breaking down five practical ways to show interest in early dating, even if you're shy, introverted, or just plain terrified. I'm covering what works, no matter how comfortable yo...

31 Mar 29min

249. What Your Dating App Profile Is Really Saying (And How to Fix It) w/ Eric Resnick

249. What Your Dating App Profile Is Really Saying (And How to Fix It) w/ Eric Resnick

I'm chatting with Eric Resnick, a dating profile expert with over 20 years of experience and 40,000+ profiles reviewed. We're discussing everything from why Bumble and Tinder are emotionally unhealthy...

27 Mar 1h 8min

248. Why Early Dating Is So Confusing Right Now (Dating Dilemmas)

248. Why Early Dating Is So Confusing Right Now (Dating Dilemmas)

I'm answering five dating dilemmas that all circle the same messy truth: early dating is confusing, and you're not alone if you feel like you and your date are on completely different planets. Dating ...

24 Mar 28min

247. The Truth About Low Libido In Relationships (And How to Get It Back) w/ Hannah Johnson

247. The Truth About Low Libido In Relationships (And How to Get It Back) w/ Hannah Johnson

I'm chatting with Hannah Johnson, aka The Libido Fairy, a sex educator with over half a million followers who helps women reclaim their desire and actually enjoy sex. We're discussing everything from ...

20 Mar 55min

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