Dating Fails



Awkward boyfriend justin bieber mixtape - 6344670208
By Unknown

Well, That's Wicked Awkward

boyfriend Awkward daughter funny - 8299977472
Via Baskin Robbins 14
cringe text conversations

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

View List

Ayyyyyy, Girl-I'm-Not-Interested-In

Awkward We Are Dating - 5091677440
By Unknown

Socially Awkward Squirrel

Awkward comic flirting Hall of Fame rage comic shy - 5360382208
20 of the most brutal rejections people have ever suffered through while on the dating app, Tinder.

20 of the Most Brutal Rejections Poor Roasted Souls Have Endured On Tinder

View List
Awkward funny Video dating - 55662849

Every Awkward Guy's Attempt to Talk to Girls

View Video
cringe dating

Coffee Shop Creeper Texts Barely Legal Barista and It's an Awkward Exchange

View List
guy texts about his penis to the wrong number

Dude Gets Himself Ruthlessly Trolled When He Texts Wrong Number to Talk About His Dick

View List
FAIL cringe Awkward texting dating - 1306117

These Cringe-Inducing Conversations Are Guaranteed to Leave Your Skin Crawling After Reading Them

View List
webcomics about dating and relationships

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

View List

Man Up

Awkward dating - 8821083392
Via distinguishedbaloney
Crazy jealous girlfriend loses her mind after another girl texts her boyfriend about the homework.

Jealous Girlfriend Goes Crazy When Girl Texts Her Boyfriend About Homework

View List
sex-ed class cringe questions

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

View List

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
cringey awkward texts from exes

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

View List
1 2 3 4 5