Flirt Fail cover art

Flirt Fail

Flirt Fail

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
Relationships Social Sciences
Episodes
  • A Tale of Two Setups
    Apr 16 2026

    This week on Flirt Fail, we’re talking setups—when your friends take your dating life into their own hands.


    One got a success story (rare), and the other? A full-blown dating disaster that quickly became one of the worst date stories we’ve ever heard.


    We break down what went right, what went very wrong, and whether setups are worth the risk… or just a fast track to chaos.


    💔 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

    Show More Show Less
    39 mins
  • Oops, I Did It Again
    Mar 26 2026

    In this episode, we're unpacking the patterns: chasing unavailable people, red flags we actively befriended, and the self-sabotage we somehow justified in real time.


    Have we learned any lessons? Debatable. But we did laugh. A lot. Mostly at ourselves.


    💔 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. 💀

    Show More Show Less
    27 mins
  • The Situationship Spiral
    Mar 6 2026

    Situationships, Flirtationships & Everything in Between


    This week on Flirt Fail, we’re diving into the confusing gray area of modern dating — the relationships that technically aren’t relationships.


    You know the ones: friends with benefits, situationships, flirtationships, and the classic “we’re just seeing where it goes.”


    We break down:

    • What these situations actually mean (and why everyone seems to define them differently)

    • The signs you might already be in one

    • Why they’re so easy to fall into

    • How to spot them early before you catch feelings

    • And how to avoid getting stuck in one if that’s not what you want


    Because sometimes the hardest part of dating isn’t rejection… it’s figuring out what exactly is going on.


    If you’ve ever thought, “Wait… what are we?” — 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


    👇 Be honest: have you ever been in a situationship?


    #FlirtFail #Situationship #ModernDating #DatingPodcast #SingleGirlChronicles

    Show More Show Less
    42 mins
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