Dating Fails

Awkward

You Will NEVER Live This Down

erection Awkward - 6866201600
Created by Unknown

When You Get Caught Staring at Your Crush

Staring Awkward funny crush - 8382149632
Via Awesome_Bro_Hug
Advertisement

Probably Happens More Often Than You Think

Awkward chatting internet to catch a predator - 6320417792
Created by Unknown
Cringeworthy couple that needs to get off of social media.

20 Cringeworthy Couples Who Need to Get Off Social Media

View List
Guy catches girlfriend cheating on him so he takes creepy photoshoot of them while they are sleeping.

Guy Catches His Girlfriend Cheating on Him so He Takes Cringefest Photoshoot of Them in Bed

View List
Advertisement
cringe Awkward Video dating Valentines day - 85223937

The Sexual Tension Is Stifling As Couples Describe the First and Last Time They Had Sex

View Video
cringe text conversations

Guy Texts Ex Trying to Set Up Threesome for Girlfriend, Girlfriend Realizes It and Pulls Brutal Power Move

View List
list KISS Awkward Memes - 1256709

When a Kiss Becomes Something Else Entirely, It's Time to Sing 'Mr. Brightside'

View List
Advertisement
People with friends that are porn stars share the most awkward moments from their friendships.

33 People With Friends That Are Porn Stars Share Best/Worst Moments During Friendships

View List
Guy creates Powerpoint presentation that proposes different ideas for his first date, and gets blocked on Whatsapp immediately.

Guy Makes Impressive First Date Powerpoint, Gets Savagely Dumped

View List
FAIL Awkward sex toys dating - 1878277

Dude Fails Terribly, Learns the Hard Way Sex Toys Are Definitely Better Not Left Out

View List
Advertisement
cringey awkward texts from exes

10 Awkward Texts From Exes That Should've Stayed In The Drafts Folder

View List
cringe dating

Stalker Chick Goes Insane On Guy In Awkward Text Rant

View List
Awkward prank sexy times funny Video - 54133761

What Happens if You Ask a Stranger for a 3some?

View Video
Advertisement

How'd the Date Go? Did You Kiss Her?

handshake-first-kiss-awkward
Via Supportsinglemoms
Awkward fapping forever alone roommates sketch Valentines day Video - 33851905

Forever Alone This V-Day? We Know What You'll Be Doing

View Video

Hot Today