Dating Fails

Awkward

Awkward prank sexy times funny Video - 54133761

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

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I Regret Nothing.

Awkward - 6925721088
By Unknown
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Girl Texts Guy Insult in an Attempt to Flirt, and Ends up Getting Stonewalled after Some Serious Awkwardness

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Via Elite Daily
FAIL Awkward baseball Video - 980997

Watch This Dude Lose Ring during His Failed Marriage Proposal Attempt, in Front of Millions of People

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webcomics about dating and relationships

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

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Guy gets friendzoned again during texting conversation and has a terrible cringe reaction to it.

Dude Gets Friendzoned (Again) and Has Shamefully Cringe-Packed Reaction

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Date flips out when she realizes that she has to pay for her own food | Hey, wann go out tonight? After did last time expect go out with again? Wow have done??9 made pay my own food and drink while paid only yours wtf

Date Has To Pay For Her Own Food, Flips Out

What a mess of a situation.
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Awkward blizzard dating FAIL - 1074949

Guy's Girlfriend Cries out Overwatch Character's Name in the Heat of Passion, and He Made the Mistake of Asking the Internet about It

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trolling Awkward prank - 78531073

Let the Gentle Caress of a Stranger's Hand Make Your Escalator Ride Uncomfortable as Hell

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cringe Awkward relationships thirsty dating - 948741

Desperate Dude Doesn't Care That This Girl Is Only Into Chicks, He Needs a First Date

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Well This is Awkward

jealous Awkward statue - 6772403456
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Probably Happens More Often Than You Think

Awkward chatting internet to catch a predator - 6320417792
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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

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

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Via Supportsinglemoms

I Sprayed My Heart Out to You!

Awkward dating graffiti marriage - 8074215168
By Unknown
Guy tries to make another girl jealous through texting conversation by pretending that he has a girlfriend and it backfires.

Idiot Pretends to Have Girlfriend to Make Another Chick Jealous and It Backfires Horribly

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