Dating Fails

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Real Men Know How to Unhook a Bra

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Via Brown Cardigan

He Looks Like a Real Go Getter

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Via Terrible Tinder Tales
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Yikes!

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Created by ToolBee

That's a Hell of a Swing

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When You Got to Have it, You Got to Have It

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Via Dash89
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Give Your Girl Some Space

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Via There Is Truth

No One Likes You...

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Via Ben Rosen

The Beginning of Caddyshack 3

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Created by Unknown
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He's One Deep Puppy

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Via Dating Is Awful

What a Generous Offer

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Via Unknown

He's Got a Great Point

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Via Brown Cardigan
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He's a Real Keeper

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Via Kevonicus

Middle School Love Notes Are the Cutest

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Via Tilly Tonka

Be a Jerk With Some Grammar Knowledge

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Via Not Okay Cupid
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This Won't End Well

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Via Littaly

Seems Like an Easy Plan

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Via unknown
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