'I still cringe': 20+ online dating mishaps from hopelessly single folks

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Ben Weiss • Writer and Editor
Jan 22, 2024 4:00 PM EST

Without physical and social cues, dating can get lost in translation really quickly. When written incorrectly, a joke can get easily misinterpreted, sarcasm can remain unclear, and the potentiality for a first date can go down the drain in an instant. This is the reality of how most relationships begin in this day and age. 

It's sort of like how actors and performers discuss the differences between auditioning and working on a play or film. Mastering the art of auditioning is its own craft, separate from the craft of acting but necessary to master in order to get the opportunity to act. Mastering the art of online dating conversations is necessary in order to even get the chance to date someone in person. It's an unfortunate element of the dating scene these days, but it's the one we're living through at the moment.

These hopelessly single folks shared their iconic dating mishaps via this thread on r/AskReddit. Keep scrolling below for the full list. When you're done, check out this story about a guy who abandoned his girlfriend in a snowstorm.

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  • 01
    I know there was some reason I swiped right on you!"
    via Tim Mossholder
  • 02
    r/AskReddit . Posted by u/dannyboy8323 6 What's your biggest fail when it comes to online dating? 7.4k Comments
    via u/dannyboy8323
  • 03
    MattSouth. Chatted with them a year by phone, once we met we had nothing to talk about and it was the most awkward encounter of my life. 27.7k ↓ Share
    via u/dannyboy8323
  • 04
    Fen_Misting Matched with someone on a dating website (before Tinder). Got to talking, seemed like a chill dude, even though there were red flags (he insisted we were dating before we met and I wasn't allowed to talk to anyone). Agreed to meet up with him at a cafe by work. Organised with my receptionist she would ring me at an allotted time and tell me I had to come back to work, so I had an out. Met with the guy for coffee, it seemed well enough, then my girl rang me, so I told him I had to get
    via u/dannyboy8323
  • 05
    A couple of months later he ended up coming into my work to see my boss. I made polite small talk with him then when he left my boss called me into her office to ask how I knew him. Turned out he was married to my bosses niece and I dodged a J bullet. Update: sorry to leave you all hanging. Boss believed me, and we never spoke of it again. I was too embarrassed to raise the subject again because I keep my private life private, and her because i assume she kept that between her and her niece. My
    via u/dannyboy8323
  • 06
    djm2491 Met with a girl at a bar in Philadelphia on a Friday night around 6PM. It was fun and we drank a lot, but I noticed that she was pacing MUCH faster than me. I had around 4 beers in the time it too her to drink 7 martinis ($15 a glass). We are getting along well and she says that she needs to use the rest room. She took her jacket and purse to the restroom. I didn't think much of it but after an hour of sitting at the bar alone waiting I realized that I got used for a heavy pregame. The b
    via u/dannyboy8323
  • 07
    dinnersateight. Oh man, the first time I contacted someone (it was via The Onion personals, which were really a thing in 2005), I just made fun of a band she said she liked. I wrote something like, "My only problem is that you are into (band)" She replied (as she should have), "My only problem is that the only thing you offer is a criticism". I still cringe. 12.1k Share
    via u/dannyboy8323
  • 08
    brucekeller. Not being exciting or witty enough in the text game. In real life my expressions and demeanor save me, not so much online. 11.1k Share
    via u/dannyboy8323
  • 09
    toaster_jack Not trying it sooner. At the end of the day, we're all just people looking to connect and share a Netflix account. 9.1k Share
    via u/dannyboy8323
  • 10
    D_Thought I matched a girl who looked really cool and complimented her hair. She responded with something along the lines of "I'm so glad you messaged me, most of these guys just match and never message." I've seen almost exactly the same line before from bots, so I assumed she was a bot and said something snarky about it. She replied, upset, and then unmatched me. 6.5k Share
    via u/dannyboy8323
  • 11
    [deleted] Putting all my eggs in one basket. Once I start a conversation with one person, I just stick with that person until I know it's not going to go anywhere. I can't deal with trying to remember stuff about two+ people at the same time. I don't mind though if the person I'm talking to is talking to more than one person as long as if we're on a date, they're not on the phone to them or mix us up. 6.3k Share
    via u/dannyboy8323
  • 12
    Zetecvan Using Plenty Of Fish, the free dating site. It was like the Netto of dating sites. I chatted briefly with one woman before telling her I was going out for a few drinks. Next day I checked my messages and she had sent some. It started with "why don't you come round to mine and get dr together", progressing to "why are you ignoring me", then to "I think you're gorgeous and we will be good together" and finally "don't you ignore me". I sent her a message the next day to never contact me ag
    via u/dannyboy8323
  • 13
    ealoft. Not realizing how much can be lost in the absence of voice inflection and physical social queues. 4.4k ↓ Share
    via u/dannyboy8323
  • 14
    ចាប់ ThatsASaabStory. I met with this very attractive woman off Upper middle class tinder (Bumble). She was way hotter than me. At some point during the evening, she leans forward on her bar stool, narrows her eyes and goes "I know there was some reason I swiped right on you". Because at this point she could not remember 4.2k Share
    via u/dannyboy8323
  • 15
    [deleted] Getting hundreds of matches on tinder but not going on a single date with someone I initially met from the app. Edit: I am a male. I've set up many dates, but get ghosted the day of. 3.2k Share
    via u/dannyboy8323
  • 16
    yeetingsmillenials Finding a wonderful guy and then cancelling the date last minute because I wasn't over my ex. Joke's on me, we rematched 10 months later, he gave me about my behaviour last time and told me because of that I had to come up with an idea now. March will mark our 1 year anniversary^ 2.6k Share
    via u/dannyboy8323
  • 17
    Kittii_Kat. Most of the fails are typical not-super-hot guy problems (almost no matches or messages, depending on the site) The biggest fail in my ex. We spent 5.5yrs together, I was super supportive of her (getting her on her feet in life, covering expenses for the first two years until she stabilized.. helped her find her first job, helped her through college, helped her get her first job after college, helped her with her first job after college..)
    via u/dannyboy8323
  • 18
    But then the moment I start struggling with money/finding a job (we moved across the country for the one she got), she kicks me out. I mean, I was struggling for a while.. about a year. A month after she kicked me out, I managed to land a job. Good times. 1.8k Share
    via u/dannyboy8323
  • 19
    syringelol Her husband You have no idea how many neglected wives are out there online and they love to omit the fact that they have husbands. Watch out for the mi. She'll break your heart and her husband will break your neck 1.5k Share
    via u/dannyboy8323
  • 20
    Udderside. I thought I had a pretty sick pickup line, which was 'you're so cute you make a baby deer look like a pile of V Needless to say, I'm still single 1.3k Share
    via u/dannyboy8323
  • 21
    500 walee1 I end up befriending the girls I meet instead of dating them. To me a girlfriend should be a friend too but that doesn't work for most people so I just have a lot of friends now. Which is all cool until you end up crushing after one of them who doesn't feel the same way about you 1.2k Share
    via u/dannyboy8323
  • 22
    catsnothats . Getting a free trial of tinder gold (on an acct I'd had for at least 8 months in 3 main geographic locations) and proceeding to swipe right on EVERY. SINGLE. ONE. Of the guys that had liked me. All 2,500 of them. Nothing other than anecdotes and thousands of messages has come of it yet. Oh also, I did this at 9pm the night before a huge college math exam....procrastination at its finest 994 Share
    via u/dannyboy8323
  • 23
    kwisssy. When I connected Spotify my bumble profile and unbeknownst to me, 3 of my top 10 artists were the wiggles, hi-5 and blippi. Pretty sure I missed a few connections because of that! 873 Share
    via u/dannyboy8323
  • 24
    ms_tigress Guys keep wanting to come over to "hang out". I live alone, not comfortable having someone I never met over. It's a major turn off for me, therefore conversation ceases there. 690 Share
    via u/dannyboy8323
  • 25
    tontokowalskie. I tried tinder for a while. After a month or so I contacted and was talking with this girl and things seemed to be going well. We had similar interests in music and movies, similar sense of humor, etc. Eventually we were talking about hobbies and I casually mentioned I played Magic the gathering. IMMEDIATELY UNLIKED. Like, she had time to receive the message, click the menu and hit unlike. That fast. 573 Share
    via u/dannyboy8323

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dating fails funny tinder tinder askreddit reddit thread online dating Reddit dating cringey cringe cringeworthy
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