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44 Awkward Dating Stories That Remind Us It’s Okay to Be Single

By:: Brian C. Miller; Cracked Writers

September 01, 2023

44 Awkward Dating Stories That Remind Us It’s Okay to Be Single

Sometimes dating becomes so awkward you don’t know what to say. The conversation just dies, and it’s so awkward. You sit in silence, and it’s so awkward. You want to leave, but you can’t, because it’s so awkward. You try to make things less awkward, but it only makes things more awkward.

Speaking of awkward, the very awkward stories below are a good reminder why it’s sometimes best to just remain single…

44

I hit it off with this girl I met at an outdoor concert. We decided to go for a drink a few nights later. Things seemed to be going well, but she weirdly kept mentioning someone named Chris ... Chris told me about this band. Chris refuses to eat processed sugar. Chris only drinks IPA beer. Of course, I asked, Who is Chris? Your brother? Haha, no! My husband! she says. But we have an open marriage. GRACKED COM — Source: 25 Painfully Awkward Moments From Your Dating History

43

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 I couldn in say I DO without you As things got hot and heavy, the bridesmaid started commenting on how much I looked, talked, and acted like my sister. She finally said she was so excited because it was like she was actually making out with my sister. My excitement shrivelled up and died. GRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

42

... TELL US NOW. MAMA'S BOY, THE SITCOM Claire F. shares, His mom came with him and sat in the booth directly behind him. She texted him what he should say for the entire meal. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

41

... TELL US NOW. FROM BAD TO WORSE Kate W. says, It started off not great when I got to the restaurant first to find out an ex of mine was the waiter. It only got worse when he forgot what day our date was and stood me up. So much fun to have an ex watch me get stood up. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

40

... TELL US NOW. STRAIGHT UP Jolene R. tells us, Не threw up in his whiskey glass. At the table. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

39

... TELL US NOW. PRINCE CHARMLESS Gabrielle H. shares, Не called me a liar because he didn't believe I had a flat tire even when I still showed up only ten minutes late. Не threatened to throw the pasta at the waitress' face if it didn't have enough alfredo sauce ... buh bye. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

38

... TELL US NOW. PAY IT FORWARD Alyson S. shares, Lackluster first date that was just not going anywhere... I offered to pay my half of the bill and he refused. We talked for a couple more days and I declined a second date, stating I just didn't see it going anywhere. Later that day he Venmo requested $15 from me to cover my portion of the dinner because he only took me out 'with the expectation of a second date. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

37

I WAS ONCE DUMPED BY EMAIL HER REASON FOR BREAKING UP? SHE WANTED TO SPEND MORE TIME WITH HER CRACKED.COM HORSE. — Source: 25 Painfully Awkward Moments From Your Dating History

36

I abruptly ended a lengthy telephone chat where I was spouting my mushy feelings of love to my date when my mom, who was listening on the extension line, said: Okay, that's enough. Mommy needs to use the phone now. A A few years later I was able to afford my first cellphone. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

35

CRACKED.COM Date took me to a fast food place. Не told me I was allowed to order from the dollar menu only. Не ordered a $6 burger. I turned around and left. — Source: 25 Painfully Awkward Moments From Your Dating History

34

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. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

33

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. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

32

Her crazy ex found out about our date, so he kept 'accidentally' running into CRACKED.COM us wherever we went that night. She was strangely flattered and said that it showed how much he still cared for her. They eventually went off together. — Source: 25 Painfully Awkward Moments From Your Dating History

31

CRACKED.COM 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 it to a girl I had just started seeing. You know, as a joke. HAHA, I'M LAUGHING. — Source: 25 Painfully Awkward Moments From Your Dating History

30

... TELL US NOW. THIRD WHEELING James D. tells us, She invited me to her favorite bar, but didn't mention it was where she hung out with her ex, whom she still lived with and who didn't know she now considered him an ex. They got into a huge fight, I finished my drink and walked out, which no one noticed. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

29

... TELL US NOW. A VALID EXCUSE Beth F. tells us, Не kept checking his watch so I finally asked if he had somewhere to be. Turned out he was on the sex offender registry and had a curfew. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

28

... TELL US NOW. STOP AND GO Heather C. tells US about a date, Не yelled 'Stop!' while I was driving down the road. I stopped right there in the road, thinking something was wrong, and he jumped out of the car and ran off. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

27

... TELL US NOW. AN ITALIAN PHARAOH Andrew В. shares, I showed up for Olive Garden. What I got was a pyramid scheme. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

26

... TELL US NOW. A ROMANTIC RIDE HOME Kelly H. tells us, Не got pulled over for no tail lights. Не went to jail (he had stolen the car) and I got to ride home in a police car. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

25

... TELL US NOW. PICTURE THIS Jessica, 32 . - Samantha S. tells US about a date, Не told me I didn't look like my picture, though my picture was just me with shorter hair and no glasses. Не told me, 'And that's not a compliment.' CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

24

... TELL US NOW. CRITICALLY PANNED Abie W. shares, Не decided I wanted to pay for us to watch The Phantom Menace in 3D. Then he asked when we were going to have sex. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

23

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. Не didn't say another word the rest of the way to the restaurant. After we parked he turned to me and said See, I'm a good driver. You don't have to wear CRACKED.COM your seatbelt. — Source: 25 Painfully Awkward Moments From Your Dating History

22

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 meeting she demanded flowers and chocolate and when I made it clear that I wasn't interested, she asked me if I could be her adoptive brother. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

21

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 in SAWKWARP TEENAGE SILENCE, CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

20

CRACKED.COM 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. AFTER ONLY TWO WEEKS ...? On our third date, she wanted to discuss a wedding. I did not go on a fourth date. — Source: 25 Painfully Awkward Moments From Your Dating History

19

CRACKED.COM Не thought he was being romantic despite audibly struggling to sniff my hair through snot. — Source: 25 Painfully Awkward Moments From Your Dating History

18

CRACKED.COM I used to date a guy who slept with his eyes open. This creeped me out so much that I broke up with him. — Source: 25 Painfully Awkward Moments From Your Dating History

17

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 never saw her again. And yes, I paid for the meal. And tipped. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

16

... TELL US NOW. A MANLY SCENT Kate F. shares, Не smelled like the tooth dust in a dentist's office. Не wasn't a dentist. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

15

... TELL US NOW. MOVING TOO FAST Laura M. shares, He asked if he and his 5 cats could move in with me on a first date. Then told me it would be good to have a woman to do his laundry again because he wears the same outfit for two weeks straight. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

14

... TELL US NOW. MARATHON LOSER Sam P. tells us, I run marathons competitively. Не had only ever ran 3 miles in his life but said he 'was sure it would translate' into him running a faster marathon time than me. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

13

... TELL US NOW. FOREIGN IMPOSTER Joshua D. says, I met this girl at a bar while faking a British/Scottish accent, drunk of course. We meet at a Panera a week later and im no longer speaking in that accent, date was basically just awkward after learning I was not indeed Scottish or British. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

12

... TELL US NOW. ALL ABOUT THE EYE CONTACT Jerri А. shares, He took me to lunch and instead of eating with me, he sat and stared at me while I was eating; for the entire 30 minutes. We talked a bit but it was mostly unblinking eye contact with me shoveling food in my face. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

11

... TELL US NOW. GETTING AN EARFUL Jess L. shares, First (and only) date, he put his finger in my ear during the movie, then put on motocross racing gloves before getting in the car to drive me home. Не asked me if I had ever 'Experienced God,' and his only functional headlight fell off somewhere on the drive to my house. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

10

... TELL US NOW. UNEXPECTED ENDING Ash В. shares, I didn't realise it was a date when she invited me out for a curry. I arrived in work gear, stoned, smelling like car-cleaning chemicals while she looked gorgeous. After eating, I fell asleep and she paid the bill. Fast forward, we've been together 11 years. CRACKED.COM — Source: Tell Us Now: 19 Awful Date Stories

9

I 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 — Source: 25 Painfully Awkward Moments From Your Dating History

8

For a DVD and chill first date I picked out and put on 1972's THE LAST HOUSE THE ON LEFT Understandably, I never heard from her again. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

7

On a date in high school I wanted to show off just how hilarious I was, so I pulled the old loosen the salt shaker lid. On my date. CRACKED COM — Source: 25 Painfully Awkward Moments From Your Dating History

6

GRACKED.COM Got a date on Tinder. We agreed to meet for dinner. Halfway through the date, he asked me what I charged. Не thought I was a hooker. When asked why, he said big boobs. — Source: 25 Painfully Awkward Moments From Your Dating History

5

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 he picked me up in the company car on his way home. SVA Vaughan - Specialty Не was a mortician. The body he'd been called to pick up was still in the back. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

4

A friend set me up on a date with this girl who told her she really liked me. We were to meet outside a restaurant. ? ? When I got ? there she looked at me all confused and told me she ? actually thought I was this other guy with the same first name. GRACKED COM — Source: 25 Painfully Awkward Moments From Your Dating History

3

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 work out. We laughed it off as a joke, but when I eventually got divorced, I found out he'd been serious and he thought I owed him a date. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

2

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 her nose pierced and it was very painful when I accidentally knocked it. Instead of a New Year's kiss I got a New Year's slap. CRACKED.COM — Source: 25 Painfully Awkward Moments From Your Dating History

1

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 lonely so I texted her while I was doing the deed. — Source: 25 Painfully Awkward Moments From Your Dating History

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