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25 Painfully Awkward Moments From Your Dating History

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Relationships are hard, and we all make dumb mistakes along the way. Misery loves company, so we asked our readers to tell us about their most awkward, embarrassing, and generally unfortunate romantic encounters.

The most painfully awkward is below, but first, the runners-up:

25
Entry by Sonny Time

asked a girl out in front of my friend. Turns out she had been secretly dating my friend and that was the day I found out. CRACKED.COM

24

For a DVD and chill' first date I picked out and put on 1972's THE LAST HOUSE ON LEFT THE Understandably, I never heard from her again.

23

On a date in high school wanted to show off just how hilarious I was, SO I pulled the old loosen the salt shaker lid. On my date. CRACKED COM

22
Entry by YepThar

CRACKED.CON Got a date on Tinder. We agreed to meet for dinner. Halfway through the date, he asked me what I charged. He thought I was a hooker. When

21
Entry by LilySprite

A guy I'd just started dating was on call at work almost all the time. One Friday night he got called to do a job but didn't want to break OUr date SO

20

A friend set me up on a date with this girl who told her she really Iiked me. We were to meet outside a restaurant. H d When I got there She looked at

19
Entry by JadeCampbell

The officiant for my wedding, a friend from college, took the groom aside and asked if he could be next in line to date me if our relationship didn't

18
Entry by LilySprite

At a New Year's party, I thought it would be romantic to grab my girlfriend at midnight for a passionate kiss..: What I forgot was she had just gotten

17
Entry by Chan Teik Onn

CRACKED COM I'm sorry bb :'( I ate some bad chicken during a date and had to spend the remaining date night on the toilet. I didn't want her to feel l

16
Entry by Buttersnix

When I got in the car, my date asked me why I was putting on my seat belt. Itold him I always wear my seat belt. He didn't say another word the rest o

15
Entry by Chan Teik Onn

A girl in college inexplicably got my number and texted me, asking me out on the pretext that she needed help with a course I had taken. During our me

14
Entry by PollyDarton

In high school I got to know my best friend's cousin through flirty instant messages. When we finally met in person, instead of hitting it off we sat

13
Entry by ChevySpoons

CRACKEDCOR On our first date, she said, 1 love you. On OUr second date, she took me to meet her parents, and her grandmother. LET'S GET MARRIED. AFT

12
Entry by Wyrmologist

He thought he was being romantic despite audibly struggling to sniff my hair through snot.

11
Entry by ERRiley

CRACKED.COM I used to date a guy who slept with his eyes open. This creeped me out SO much that 0 broke up with him.

10
Entry by CornishPlasty

Took a date to a fancy restaurant. The waiter was a friend of her friend. She ended up flirting more with him than me, and even took his number. I nev

9
Entry by boffredi

I WAS ONCE DUMPED BY EMAIL HER REASON FOR BREAKING UP? SHE WANTED TO SPEND MORE TIME WITH HER HORSE. CRACKEDCON

8
Entry by masta_X

0 abruptly ended a lengthy telephone chat where 0 was spouting my mushy feelings of love to mY date when my mom, who was listening on the extension li

7
Entry by YepThar

CRACKEDc Date took me to a fast food place. He told me I was allowed to order from the dollar menu only. He ordered a $6 burger. I turned around and l

6
Entry by LilySprite

I got set up on a blind date... I'd already been out with him and ignored his calls after we didn't hit it off.

5
Entry by munagam07

I had a blind date with a guy who kept slipping sales pitches into our conversation. He'd even brought all the brochures and catalogs with him.

4
Entry by TaiGin

Her crazy ex found out about our date, SO he kept 'accidentally' running into us wherever we went that night. She was strangely flattered and said tha

3

My favorite local band played a set on a local radio station. I called in and asked them to play their song about a man stalking a woman and dedicate

2
Entry by Scott Laffey

25 Painfully Awkward Moments From Your Dating History

1
Entry by jimclass

At my sister's wedding, I hooked up with one of the bridesmaids, who had been her college roommate. thank you for being my BRIDESMAID Icouldn't say I

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For more, check out Rookie Relationship Mistakes You Made When You Were Younger and The 22 Most Awkward Moments From Your Dating Life.

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