Dating Fails
Advertisement

Awkward

I Sprayed My Heart Out to You!

Awkward dating graffiti marriage - 8074215168

Maximum Hover-Hand

Awkward date hover hand - 7960735232
Advertisement

UR PURTY WANNA BE MAI GURLFREND

Awkward eye contact - 6040308992
webcomics about dating and relationships

Dating is Hard Nowadays, Let These Web Comics Caress Your Tender Heart

View List
People describe their worst first dates and they are maxed out on cringe.

People Describe Top 10 Worst Dates They've Ever Suffered Through

View List
Advertisement

Yeah I Love It

cyanide and happiness Awkward - 6981035520
Via Cyanide and Happiness

Hit That One On The Nose

dating-fails-hit-that-one-on-the-nose
Via acidcow
Guy gets rejected in terribly brutal manner, and goes viral after the conversation is shared on Twitter.

Guy Goes Viral After Getting Rejected In Most Savage Way Possible

View List
Advertisement
Girl live-tweets extremely entertaining and awkward date with old man she meets through OkCupid Dating Service.

Girl Live Tweets Cringe-Soaked Date With Old Man She Met On OkCupid

View List
naked news cringe Awkward australia - 85750017

Dude Laughs Off Girl's Savage Assessment of His Naked Body On Unbelievably High Cringe TV Show

View Video

Well That's Going To Make Any One-on-One Meetings Awkward and Hard(er)

funny dating image new boss is an old tinder match that sent dick pics
Via The Sun
Advertisement

That Awkward Moment When...

Awkward cheating dating - 8803692800
Via bossip

Girl Texts Guy Insult in an Attempt to Flirt, and Ends up Getting Stonewalled after Some Serious Awkwardness

girl-insults-guy-for-no-reason-in-flirt-attempt-and-things-get-real-awkward
Via Elite Daily
sex-ed class cringe questions

People Share the Most Cringe-Worthy and Hilarious Questions That Were Asked During Their Sex-Ed Classes

View List
Advertisement

This Date Got Awkward

first date Awkward Cats funny Rage Comics - 8116424448
Via See Mike Draw

You, too!

dating-fails-you-too
Via distinguishedbaloney
Advertisement

Hot Today

Advertisement