#datingfail
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arhettersauthor.bsky.social
Virgilio thought it was a good idea to date three women at the same time.

It didn’t occur to him that they could crumple him like a soda can.

#virgiliochronicles #BookSky #IndieAuthorSky #datingfail
Supernatural Dating (Virgilio Chronicles)
Supernatural Dating (Virgilio Chronicles) [Rhetters, Alex] on Amazon.com. *FREE* shipping on qualifying offers. Supernatural Dating (Virgilio Chronicles)
www.amazon.com
September 18, 2026 at 2:10 AM
rhondababe.bsky.social
Um, I don’t want anyone “all the way in” my gut…. and this is Civ dating/flirting 😭😩🫠🫠🫠 #datingfail
September 9, 2026 at 7:37 AM
genzhype.bsky.social
@itskaileyanna's date got canceled cuz she's an influencer? They cited "lifestyle concerns" and "social media appearance." Wild. #InfluencerDrama #DatingFail https://genzhype.com/drama/influencer-s-date-canceled-over-online-presence-sparks-debate/
GenZHype
September 2, 2026 at 12:59 AM
cryptidboyz.bsky.social
Down to Earth

An encounter that’s certainly… grounded. 😂🌱📏😳

#DatingFail #SmallTalk #Humor #Awkward
August 27, 2026 at 12:00 PM
anelsonlmpotter.bsky.social
even romance writers have horror stories 🤣
www.NelsonPotter.com
#romace #writingcommunity #writers #authors #NelsonPotter #datingfail
August 23, 2026 at 5:55 AM
sweettoothyandere.bsky.social
Also they’re ugly and can’t sing. 😝

Makeup: alchemist_beauty (IG)
Hair color: _dlo1 (IG)

#musicianproblems #musicianmemes #datingfail #gothgirl #altgirl
August 14, 2026 at 6:15 PM
videocurator.bsky.social
I'm still trying to wrap my head around why this guy thought he could casually drop "Helen of Troy is actually a black woman" into our conversation and expect me to be fine with it. Needless to say, that date ended quickly.

Source

#Racism #DisasterDate #DatingFail #Misogyny #Ignorance
July 17, 2026 at 1:45 AM
www.threads.com/@niquiebknow...
Brenique Reed (@niquiebknows) on Threads
He mad she protected her drink?! 🚩 Instant red flag 😳 #datingfail #relationshipdrama
www.threads.com
April 13, 2026 at 11:49 PM
debz59.bsky.social
www.tiktok.com/t/ZTkfk3y3E/
He mad she protected her drink?! 🚩 Instant red flag 😳 #datingfail #relationshipdrama
TikTok video by Brenique Reed
www.tiktok.com
April 13, 2026 at 6:54 PM
stevyturmel.bsky.social
LE GUIDE ABSURDE des approches romantiques RATÉES 😂
Tu veux savoir comment GARANTIR ton célibat à vie ?
Ce guide vintage des années 80 te montre EXACTEMENT quoi ne pas faire !

#HumourQuebecois #sora #DatingFail #Vintage80s #Sketch
March 21, 2026 at 2:02 PM
lukeattheroost.bsky.social
She thought opening up the marriage would spice things up. He's living his best life while she can't even get a text back.

#lukeattheroost #podcast #openmarriage #relationshipfail #backfired #datingfail #awkward #ouch
March 4, 2026 at 11:41 PM
danasinspired.bsky.social
👉 I dated a firefighter once. It didn’t go well…
#bigotry #racism #datingfail
Firefighter fantasy
YouTube video by danasinspired
youtu.be
February 21, 2026 at 6:36 PM
talkingwithdonato.bsky.social
Dating app disaster! He thought he found a connection, but she brought a child on their first date and expected him to pay. Awkward! He paid for his drink and left. Was he wrong? A real man would have stayed? #DatingFail #FirstDate #Podcast
January 20, 2026 at 8:34 PM
thoughts-to-my-ex.bsky.social
You think it would be this simple?
#datingfail #hesnotworthit
www.tiktok.com/t/ZP8fjpcgr/
Silly me !!!
TikTok video by mel
www.tiktok.com
January 13, 2026 at 3:42 AM
thoughts-to-my-ex.bsky.social
Let me count the ways:
1. Validationship (him)
2. Denialship (me)
6. Manipulationship (him)

#redflags #datingfail #hesnotworthit

www.tiktok.com/t/ZP8fjQThK/
situationships are OUT. here is what’s IN #situationships #datingadvice
TikTok video by mel
www.tiktok.com
January 13, 2026 at 3:39 AM
salty4848.bsky.social
#FirstDateEnergy #AwkwardComedy #DatingIn2026 #DryHumor #CringeButHonest #DatingFail #DarkComedy
January 3, 2026 at 12:39 AM
codigosleonora.bsky.social
Los incels no existen, ¿Si o no?
#BlackPill #DatingFail
November 8, 2025 at 11:00 PM
trumpwatch.bsky.social
“MAGA men in D.C. are struggling to find dates in the conservative scene, lamenting that women aren’t as attracted to them as they hoped: ‘Not as masculine as I expected.’ Politics isn’t the only thing in crisis… 😬 #DatingFail #DCPolitics #MAGA www.rawstory.com/maga-2674239...
MAGA men come up lacking on DC's conservative dating scene: 'Not as masculine as I hoped'
MAGA followers are reportedly struggling to find suitable matches in Washington, D.C., complaining that the conservative dating scene is not what they expected.The challenge is tough for conservatives...
www.rawstory.com
October 30, 2025 at 2:55 AM
mr-jociriju.bsky.social
Which came first: not getting a date or buying a Cybertruck? The ultimate chicken-or-the-egg for the modern age. Discuss below. 👇 #cybertruck #datingfail #bigquestion
October 17, 2025 at 12:36 AM
mr-jociriju.bsky.social
Which came first: Not getting a date or buying a Cybertruck? Discuss. Is it a magnet for attention or a repellent for romance? Asking for a friend... who definitely doesn't own one. 😉 #DatingFail #CybertruckProblems #Relatable
October 17, 2025 at 12:09 AM
suburbanfairytales.bsky.social
Has anyone ever actually done this while you were on a date with them? 😬

Get early access to my newest comics on Comics Kingdom! comicskingdom.com/suburban-fairy-tales

#illustration #fun #pigs #webtoon #cute #myart #datingapp #datingfail #baddate #firstdate
September 24, 2025 at 4:46 PM