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Flirt Fail

Flirt Fail

Written by: Syd West
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About this listen

I’m 31, have never had a boyfriend, and my one real date ended in chaos—so now I’m turning my tragic love life into a comedy experiment. With the help of dating mentors aka my best friends, I’m navigating swipes, red flags, and cringe-inducing encounters while you laugh, learn, and maybe feel grateful you’re not me. Think rom-com meets reality show—minus the happy ending…for now. 💔 FOLLOW & LISTEN TO FLIRT FAIL 🎧 Listen on Spotify: https://spotify.com/flirtfail 🍎 Apple Podcasts: https://applepodcasts.com/flirt-fail 📱 TikTok: https://tiktok.com/@flirt_fail 📸 Instagram: https://instagram.com/flirt_fail ▶️ Subscribe on YouTube: https://youtube.com/@flirt_fail New episodes every 3 weeks — more flirting, more failing, same emotional damage. 💀

imaflirtfail.substack.comSyd West
Episodes
  • Lessons From Their Love
    Feb 12 2026

    Hindsight Is 20/20 (Growth Was Required)


    This week on Flirt Fail, I sit down with two of my recently engaged friends to talk about what their relationship actually looked like before the ring.

    Spoiler: it wasn’t instant clarity and rom coms.

    We unpack:

    • The relationships they had before each other

    • The mistakes they made (and what those mistakes taught them)

    • The timing that wasn’t right… until it was

    • How they realized this time felt different

    • And why growth had to happen before commitment could

    But this isn’t just their reflection tour — it’s also my intervention. They break down what they wish they knew earlier and what I absolutely should not repeat if I’d like to avoid unnecessary emotional damage.

    Because sometimes you don’t need to learn the hard way… if your friends already did.

    If you’ve ever wondered whether timing matters, how people really know, or how to avoid sabotaging something good — this episode is honest, hopeful, and slightly aimed at me.


    💔 New episodes every 3 weeks

    👇 Do you believe in right person, wrong time — or just right growth?


    💔 FOLLOW & LISTEN TO FLIRT FAIL

    🎧 Listen on Spotify: https://spotify.com/flirtfail

    🍎 Apple Podcasts: https://applepodcasts.com/flirt-fail

    📱 TikTok: https://tiktok.com/@flirt_fail

    📸 Instagram: https://instagram.com/flirt_fail

    ▶️ Subscribe on YouTube: https://youtube.com/@flirt_fail

    Show More Show Less
    44 mins
  • First Date Fumbles
    Jan 22 2026

    First dates sound cute in theory. In reality? They’re a social experiment with snacks.

    In this episode of Flirt Fail, we’re talking everything first dates — what to say, what to avoid, and how to escape without an “emergency” phone call from a friend.

    We get into:

    • Conversation topics that kill the vibe instantly

    • Where to go on a first date (and where NOT to)

    • How to end a date gracefully…or not

    • And first-date horror stories that should qualify as public service announcements

    If you’ve ever gone on a date and immediately texted your friends “I hate it here,” this episode is for you.

    💔 FOLLOW & LISTEN TO FLIRT FAIL

    🎧 Listen on Spotify: https://spotify.com/flirtfail

    🍎 Apple Podcasts: https://applepodcasts.com/flirt-fail

    📱 TikTok: https://tiktok.com/@flirt_fail

    📸 Instagram: https://instagram.com/flirt_fail

    ▶️ Subscribe on YouTube: https://youtube.com/@flirt_fail

    New episodes every 3 weeks — more flirting, more failing, same emotional damage. 💀

    #FlirtFail #DatingPodcast #SingleGirlChronicles #ComedyPodcast



    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit imaflirtfail.substack.com
    Show More Show Less
    48 mins
  • How to Survive Men by Men
    Jan 2 2026

    This week on Flirt Fail, I invited two of my guy friends to give the male perspective on all things dating — and shockingly, they had a lot to say.We break down:• How guys actually want to be approached IRL• What men look for on dating apps (and what instantly makes them nope-out)• Why flirting feels like a group project we’re all failing• AND… the moment they brutally, lovingly, aggressively reviewed my dating profileSpoiler: men noticing the tiniest things while missing the obvious? Groundbreaking.If you’ve ever wished you could peek inside a guy’s brain without actually dating one, this episode is for you.



    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit imaflirtfail.substack.com
    Show More Show Less
    48 mins
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