You're Too Picky | Dating, Relationships, Millennial Women

Hey friends—real talk? I haven’t dropped a You’re Too Picky episode in over a month. Between summer slowdown and my own capacity hitting a wall, something had to give.

This little chaotic dating podcast has been such a fun ride... but I’ve realized I can’t keep running two separate shows. So we’re evolving.

Starting now, You’re Too Picky will live on as a bonus dating series inside my other show, Burnout-Proof. Same vibe, same voice, just one home that’s easier to maintain—and honestly? Makes way more sense for my life right now.

Don’t worry: the archives are staying up, and I’ll keep dropping new “Too Picky” episodes when I’ve got dating chaos worth ranting about. But for now? Follow me over on Burnout-Proof and keep an eye out for episodes labeled You're Too Picky.

We’re still dating while ambitious. Still burnout-prone. Still hot messes. We’re just doing it smarter.

👉 Follow me on Instagram: @coachellyn
🎧 Listen + subscribe to Burnout-Proof: https://www.coachellyn.com/burnout-podcast
📬 Submit your dating fails, red flag debates, or stories: coachellyn.com/picky/submissions

Stay picky, babes. I’ll see you over there. 💅

Ever had someone start teasing you on a first date—and it didn’t land?

Yeah, me too.

This week, I’m diving into the weird little world of early relationship ribbing. Because I don’t care how many dating podcasts say "banter is flirting"—if I just met you, and you're already poking fun at my tattoos or my career? We're not flirting. You're being disrespectful.

Follow me on IG ⁠⁠@youretoopicky⁠⁠ and share your own stories: ⁠⁠⁠Submit anonymously here⁠⁠⁠.

In this episode, I talk about:

• The "8 Mile effect" and why we call ourselves out before others can

• The difference between playful teasing and crossing a boundary

• Why I actually think early ribbing is a red flag

And if being "too picky" means you don’t give strangers permission to make fun of you? Then yeah. I’ll own that.

What do you do when a date isn’t bad… but isn’t great either? In this week’s episode of the You’re Too Picky podcast, I break down a date that was the definition of “meh.” No sparks, no drama—just two hours of pizza, coffee, and a guy who could only talk about food.

Follow me on IG ⁠@youretoopicky⁠ and share your own stories: ⁠⁠Submit anonymously here⁠⁠.

We're talking:

• The fine line between giving someone a chance and wasting your time

• Why “not bad” isn’t the same as worth seeing again

• How to handle dates where the vibe is just… flat

• Why you don’t owe anyone a second shot just because they paid for lunch

If you’ve ever felt guilty for not giving someone a second chance just because they were nice, this one’s for you.

🎧 Listen now on Spotify, Apple Podcasts, or wherever you get your fix.

In this episode of You're Too Picky, I'm taking you on a wild ride through the most bizarre and hyper-specific dating apps and groups I could find across North America. Think ghost dating, clown dating, conspiracy-theorist matchmaking, and apps based on your salad order. I'm serious.

We're talking:

• The apps for those who are literally ride or die (hello, Ghost Singles)

• What happens when your beard becomes your dating profile

• Niche apps that are either genius or absolutely unhinged (maybe both?)

• How identity, lifestyle, food, and even fetishes turn into full-on dating platforms

You’ll laugh, cringe, and probably question your entire online dating strategy by the end of this one. But also... it proves there really is someone out there for everyone.

Follow me on IG @youretoopicky and share your own stories: ⁠Submit anonymously here⁠.

Buckle up, because this week’s episode is basically a dating fever dream—and it all came from ONE listener’s DMs. (Girl, you know who you are 👀)

Ellyn dives into a buffet of dating shenanigans courtesy of one brave soul who submitted everything from questionable Facebook ads to cruise ship heartbreak. Segments today include:

• 🚩 Red Flag or Nah? — He ghosted her after the second date… then matched again a year later. Sir, do you not own a brain cell?

• 💀 Dating App Fails — When your opening line backfires spectacularly and you don’t even realize you’ve dated her before.

• 🤨 WTF Dating App Moment — “I’m like Eeyore. Clinically depressed…and hung like a donkey.” We have questions. And also, applause??

• 📞 Too Picky Hotline — The cruise ship love story that had her falling in a week… and crying the next. Love bombing? AI-generated texts? Erectile dysfunction? It’s all here.

PLUS: Ellyn shares her own Notion-based dating dashboard and a few hard-earned lessons about second chances and why reconnecting with old matches is usually a trap.

You’re not too picky—you just have standards. And if those standards include working penises and not being love bombed on a boat, you’re in the right place.

🎧 Listen in, laugh hard, and send your chaos to: https://www.youretoopicky.com/submissions

In this episode of the You're Too Picky podcast, I’m throwing it back to exactly one year ago when I met a guy on the 4th of July—and it somehow turned into four months of lukewarm texting, weird memes, and “are you free right now?” phone calls.

This guy? Not quite a stage 5 clinger. More like a solid stage 3. But it got weird. From Insta-stalking my stories to texting me at 5:45 AM with “we should do attractive things,” it was a slow, cringe-filled spiral that ended with him texting me TWO months after I said I wasn’t interested. Bro. Take the L.

In this episode I talk about:

• The moment I realized I didn’t owe this guy anything

• How not being into someone is enough reason to move on

• Why “drop everything and hang out with me” is not a love language

• When ghosting becomes self-preservation

If you’ve ever been quiet-quit someone who wouldn’t quit you, you’ll feel this one.

Follow me on IG @youretoopicky and share your own stories: Submit anonymously here.

In this episode of the You're Too Picky Podcast, I'm talking about a wild (or just interesting...?) update: my MOM wants to set me up on a blind date.

Is this what hitting dating rock bottom looks like—or is it the start of a Hallmark movie arc? I'm spilling the tea on the text that started it all, her mixed feelings about community matchmaking, and why she's both mortified and lowkey into it.

But that’s not all.

This week’s segments are unhinged in the best way:

• Red Flag or Not: Pet names like "babe" before date two? Sweet or sketch?

• WTF Dating App Moment: When a convo about her business got real gross, real fast (OnlyFans guy, we’re looking at you).

• Dating App Fail of the Week: A Hinge profile with ZERO face pics, just blurry mountain shots and some truly unhinged prompts. Are we dating or booking a national park tour?

Share your stories and vote on this week’s Red Flag or Not: Submit anonymously here — we might feature yours on a future episode!

Follow Ellyn on Instagram @youretoopicky and don't forget: new episodes every Friday.

Welcome back to the You’re Too Picky Podcast— helping you date, not settle.

I'm sitting down with my friend Michal Kaye, a single Jewish woman living in Israel, to unpack what dating looks like across generations, cultures, and belief systems—yet feels remarkably the same.

📲 Follow the pod on IG: ⁠@youretoopicky⁠

📩 Submit your story or rant: ⁠youretoopicky.com/submit⁠

🎤 Leave a voice note to be featured: Tap the “Hotline” tab on the site

📸 Tag and share your fave line: ⁠@youretoopicky⁠ + ⁠@coachellyn

Timestamps & Highlights:

• 00:00–04:00 – Meet Michal & Ellyn: Gen X vs Millennial perspectives on dating

• 04:00–10:00 – Orthodox vs non-Orthodox—how religion shapes expectations

• 10:00–18:00 – Dating app rituals, first-date red flags, and spiritual sabbath deal breakers

• 18:00–25:00 – When dating feels like matchmaking—values, magnetism & metrics

• 25:00–32:00 – Is it fair to ask him to ask about your business? How much curiosity & respect matter

• 32:00–40:00 – Boundaries, attachment styles & the games we unknowingly play

• 40:00–47:00 – Michal’s “flow vs control” approach and why letting go helps

• 47:00–55:00 – Business owner boundaries meet dating life: what’s public, what’s private

• 55:00–1:00:00 – Relationships are run like brands: What boundaries & self-care look like

Why You’ll Love This:

• A rare cross-generational perspective on dating dynamics

• Real talk on Jewish dating traditions, values, and sabbath deal-breakers

• Insight on honoring both professional AND personal life in relationship conversations

• Practical tips on spotting red flags, staying grounded, and pursuing healthy attachment

Resources Mentioned:

• Dating coach check-ins & boundary-building

• Michal’s value-list breakdown (friends, family, faith, flow, fun)

• Ellyn’s framework for red-flag detection

• 💌 Submit your dating stories & questions here for future group episodes

Ready to do better than “WTF Dating”?

📲 Follow the pod on IG: ⁠⁠@youretoopicky⁠⁠

📩 Submit your story or rant: ⁠⁠youretoopicky.com/submit⁠⁠

🎤 Leave a voice note to be featured: Tap the “Hotline” tab on the site

📸 Tag and share your fave line: ⁠⁠@youretoopicky⁠⁠ + ⁠⁠@coachellyn⁠

Stay picky, stay powerful—see you next Friday.

Someone recently said, “It’s not the apps—it’s the people on them.”

My response? Nah. It’s the apps.

And this episode is the full rant you’ve been waiting for.

Today, we’re breaking down exactly how dating apps have gone from cute convenience to full-blown pay-to-play chaos—and why that shift is making it way harder to find anything real.

💸 We’re talking:

• Gamification, swiping limits, and “roses” that cost real money

• Why love now has an algorithm you have to beat

• How we’ve monetized not just the apps—but being on them

• The dating coach industrial complex (no shade, but also… c’mon)

This isn’t about being bitter. It’s about naming the bullshit that’s draining your time, your wallet, and your emotional energy.

📲 Follow the pod on IG: @youretoopicky📩 Submit your story or rant: youretoopicky.com/submit🎤 Leave a voice note to be featured: Tap the “Hotline” tab on the site

📸 Tag and share your fave line: @youretoopicky + @coachellyn

If being picky means expecting more than a subscription and a swipe to find something real?

Then yeah—I’ll stay picky. And I hope you do too.

New episodes every Friday.

Ever walked away from a “perfectly nice” date and still felt off about it? That’s not you being dramatic—it’s your intuition doing its job.

In this episode, we’re diving into the subtle (and not-so-subtle) moments when your gut speaks up and what it actually looks like to listen.

🔮 Here’s what we’re getting into:

• The Planner Guy who expected me to plan the date… because I said I liked calendars?

• • Why trusting your dating gut isn’t judgment—it’s clarity

  • That one date that was fun… but just not it (aka, Disc Golf Guy)

  • The man who turned “what are you into?” into a full fantasy checklist (including talons and lawn maintenance 🫠)

  • The difference between curiosity and objectification

  • Three questions to help you gut-check any interaction

📲 Follow the pod on IG: @youretoopicky

💬 Submit your stories for future segments like Red Flag or Nah, Too Picky Hotline, and WTF Dating App Moment at coachellyn.com/submissions

📸 Tag & share your fave line: @youretoopicky + @coachellyn

If listening to your intuition is “picky,” I’ll take it.
New episodes every Friday. See you next week.