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Dating is something that takes a lot of guts and experience from everyone who wants to be good at it. But nobody, not even your friend Trevor who spends all of his weekends chasing Tinder matches, is safe from making a fool of themselves. And some of these misfires can be painful not only for the two people who are on the date, but to everyone around them.

To prove this point, I'll ask you to take a look at the subreddit r/SadCringe. It's a place for awkward and/or embarrassing situations that also make your heart ache, and while we have already covered it in one of our older publications, this one is dedicated exclusively to pathetic attempts of winning over others.

I don't know if we should feel sorry for these folks or not — many from this bunch sound like they would fail a test in common decency. But let's try to judge their behavior rather than their personalities. If that's possible.

#1

Life Stops Right At 35

Life Stops Right At 35

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DennyS (denzoren)
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Dude...just...you insult her out of the gate and then pretend like you're not interested when she turns you down...just...stop.

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#2

Just A Normal Guy

Just A Normal Guy

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#3

Guy Thinks A Girl Was Begging For Sex When She Was Nice To Him At Lunch

Guy Thinks A Girl Was Begging For Sex When She Was Nice To Him At Lunch

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#4

Incels Online Are Cringe. In Person? Even Worse.

Incels Online Are Cringe. In Person? Even Worse.

Horny_Weinstein Report

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DUN DUN (she/her)
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

This is so bad, so fricking bad! These types of people belong in mental asylums, if not jail.

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#10

Poor Guy

Poor Guy

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That nerd Zoe
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I JUST REMEMBERED a while ago I said I was lesbian online and this dude was arguing that it's a sin and then someone else said "Bro ur just mad she gets more girls than you" 💀💀

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#11

'He Was Bleed From His Mouth'

'He Was Bleed From His Mouth'

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DUN DUN (she/her)
Community Member
2 years ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Would've considered if it said "Hi it's Josh now just got back from the afterlife"

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#12

I Posted In Another Sub About Wanting A Breast Reduction. I Just Got This Message

I Posted In Another Sub About Wanting A Breast Reduction. I Just Got This Message

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#13

This Guy Is An Alpha Male

This Guy Is An Alpha Male

MurderousLamb Report

#15

Homie Just Kept Going

Homie Just Kept Going

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Elsie
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Genuine Guy.. my asz there's a spot on the predators list in this guy's future

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#17

Just Gonna Drop This Right Here

Just Gonna Drop This Right Here

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#19

Did Ian Mean Anything To You?

Did Ian Mean Anything To You?

icant_shit Report

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Jo Choto
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My child died two minutes ago, so I'm going to get right on this chat with this random girl and tell her about it. Yup, I'm convinced.

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#21

My Friend Who Ive Known For Around A Month

My Friend Who Ive Known For Around A Month

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#24

I Thought You Were A Good Person

I Thought You Were A Good Person

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KJ
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

But he doesn't specify which variety! Does he mean Blue tits, Coal tits etc, it's quite a long list.

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#25

Bruh

Bruh

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Susan Trevaskis-Owen
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm surprised the artist(s) didn't try to talk him out of it, or refuse to take the commission(s).

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#26

My Ex From High School Sent Me A Snapchat Video Of Him Begging Me For Nudes, And It Got Worse

My Ex From High School Sent Me A Snapchat Video Of Him Begging Me For Nudes, And It Got Worse

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May
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I have to stop here - I have found my gross out limit. Turns out it's 'Mommy'

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#28

Promo Code “Cutie”

Promo Code “Cutie”

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User# 6
Community Member
2 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

WTAF is wrong with these people, are they really so dimwitted they think these sickening texts would persuade anyone into doing anything other than blocking them?

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#30

I Felt This In My Soul

I Felt This In My Soul

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Xottel
Community Member
2 years ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I love the joke. Also I'm more concerned about the boyfriend invading their privacy, tbh.

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Note: this post originally had 67 images. It’s been shortened to the top 30 images based on user votes.

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