Awkward Dating Stories

Discover your favorite Spotlight videos related to Awkward Dating Stories. Last updated 1/19/2026

Nandi Summers

dating stories funny anecdotes dating fails dating funny anecdotes Olivia O'Brien Messy by Olivia O'Brien music

#awkward #sold #selling #datingtips

LifeofJr

comedy skit funny joke husband wife bar comedy jokes humor first date

#funny#stories#comedy

💜Jess💜

dating site marriage awkward encounter funny story relationship Pharrell Williams Happy song blue hair colorful glasses

So did we match??? #dating #poly #flirting #relationship #datingapps

Michael Dapaah 😂🤔

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Michael Dapaah 😂🤔

The dating game is wild out here ❤️❌ #dating #love #relationships #shxtsngigs #podcast #show

Best of Iman Gadzhi

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Best of Iman Gadzhi

How Iman sets up Amara's dates

Roro

arranged marriage dating horror stories dating problems Target store cheating Miami Halloween party friends stories Target

#marriage #relationships #real #relatable

🧃🐽🦓Honor🦓🐽🧃

we broke up relationship story breakup story awkward moment communication mishaps personal story

🧃🐽🦓Honor🦓🐽🧃

Abicha

dating dream suddenly attractive irl crush dream about someone unexpected crush relatable story dream logic crush dream story

Follow for more chat

ANGELA CARLOS

funny dating story relatable dating story awkward woman

Liam Welsh

autism Eric Cartman impression comedy sketch awkward date self-discovery impression Cartman

Liam Welsh

flirting after long term relationship awkward flirting dating after relationship flirting tips grocery store flirting fails dating humor flirting

Tyler Vitelli

funny excuse to turn someone down dating scenarios school dating high school school hallways anecdote storytelling school hallways

Seemed like the only solution #storytelling #funny #relatable

ryanmmichaels

Dallas Texas Dallas Texas Online dating CupcakKe Bacon song

Eva Langwin

funny skit awkward text train

ain’t that just the way

༘⋆Heather Nicol ₊˚ෆ

age gap relationships awkward encounters relationship humor time out personal stories

༘⋆Heather Nicol ₊˚ෆ

Regena

expired crush used to have a crush on you dating dilemma relatable

#snapchatfun #viral

claysworld official

ghosting social experiment restaurant romance meet party

claysworld official

nah Marlon is cooked 🤣😭 #marlon

How To Kill An Hour Show

How To Kill An Hour Show

Dating problems

Thelolpodcast

college life awkward relationship moments ankle sprain story funny podcast podcast story college stories college podcast

Is This Story Real?

Experiment 626

pros and cons of dating me road trip self-deprecating humor relatable content mental health humor childhood trauma humor Sia hey boy hey boy Sia dating me dating life funny life

Amble

awkward family moment first meeting with in-laws pregnancy announcement embarrassing stories family dinner boyfriend's family relatable stories embarrassing moment family dinner

#ambleapp #languagelearning #languagelesson #lifeabroad #speaklikealocal

Are You Okay?

street interview first date stories pet peeves Hollywood Walk of Fame Los Angeles bar mitzvah dinner parties chewing superstitious graduation Stevie Wonder Superstition

rsvp-ing 'no' to boring pasta parties 🍝🕯️

nate

unexpected relationship

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SHXTSnGIGS

bad day silence podcast clip host ex

crush stories relatable dating stories car

😂

Nikos Andreass

gay social interactions man in car story time men car interior

Captions_BBA6DC

акино

villain story social media post awkward social moments brutal rejection hallway proposal social media rejection proposal fails social

ryanmmichaels

relationship stories awkward moments relationship fails boyfriend screenshots personal anecdote home

Chanel West Coast

embarrassing moments relatable comedy moments house

Chanel West Coast

Alex Griswold

true story stalker awkward love young love adolescence beach

unfortunately a true story

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