17 Insane First Dates That Made Women Realize These Dudes Were NOT Worth a Second Chance
Ever had a first date so bizarre you wondered if you were on a hidden-camera show? Well, you’re not alone. Let’s dive into 17 jaw-dropping stories where women quickly realized that a second date was completely off the table. Get ready for laughs, eye-rolls, and a few moments that’ll make you question how these guys even made it to date number one!
1. “He Suggested Pushing Me Into the Water—Seriously.”
“I went on a first (and last) evening date years ago. I wore a long black summer dress, and as he and I walked along the Seaport District in Boston, the sun had set. The sky became dark, and the streetlights were spaced apart. As we walked through a dark little stretch, he casually said that if he pushed me into the water, no one would notice. When he asked to see me again, there was no second-guessing that hard ‘no.’” — @artisticpizza47
2. “He Had a Kid, But ‘Don’t Worry,’ He Never Sees Him”
“Earlier this year, I went on a date with a guy I met on Bumble. We met at a coffee shop and had a nice time, and then he casually mentioned he had a kid who was a little over a year old. I was 23 then, so I felt like I was too young to play stepmom. At the end of the date, I politely told him that although I had a great time, I didn’t see us going anywhere. He told me that if I’m concerned about his kid, I shouldn’t be worried because he lives out of state with his mom, and he hardly sees him, so I’ll never have to ‘deal with him’ (yes, those were his exact words).” — @dizziestbitch
3. “He Left Me Alone FOUR Times to Smoke”
“We ran into someone he knew on the walk to the restaurant, and he talked to her for five minutes without introducing us. He announced to everyone around us that we were on a first date, and he was trying to impress me. He left me alone at the table four times to smoke, then chided me for reading my phone when he got back from one such smoke break. He insisted I eat food I didn’t want to eat. And then, during the get-to-know-you chit-chat, he made a huge show of being horrified by my brother’s death. Five minutes later he asked if I had any siblings—I said no.” — @annab4fef789d4
4. “Casually Admitted to Stalking Me”
“This guy struck up a conversation with me when I was grocery shopping, and we exchanged numbers. We met up for coffee a few days later, and it was fine at first until he admitted he’d been casually ‘stalking me,’ waiting for the perfect moment to ask me out (I should have run then). He then went into a detailed description of everything he wanted to do to me sexually. I ended the date at that point and thought that was that. He texted me later, saying he had a great time and that for our second date, we should go get ice cream and take it back to his place so he could lick it off my body.” — Anonymous
5. “Venmo Requested Her for the Cost of Her Drink”
“This happened to my friend. She went on a date with a guy, and he was interested in her, but she wasn’t so interested in him. She politely told him ‘no’ about going on a second date, then woke up the next morning with a Venmo request from the guy for the cost of her drink. Her Venmo was private, and he had to look up her last name since they met via a dating app.” — @skipnees
6. “Took Me to a Strip Club”
“I went on a date with a man who I met through a dating app. I quickly found out that he lied about his age—he was actually 10 years older than me, and he was recently divorced. He then took me to a gentleman’s club 30 minutes away. He kept saying, ‘You’re like a sister [to me]’ on the way there while stroking my leg because of how ‘awesome I was’ to agree to go see strippers with him. After the show, he drove us back drunk and speeding in his convertible. He was messaging other women on the dating app at the same time. He ended the night by saying, ‘So I’ll be hearing from you again? Because I’m such a cool guy, and dates with me are the best.’” — u/[deleted]
7. “Professed His Love—Before the First Date Ended”
“We matched on a dating app, and he kept messaging me persistently, but he seemed like a nice guy. So he picked me up and took me to a decent sushi place. The actual dinner went fine, aside from him being VERY nervous and visibly sweating. As he drove me home, he continually asked if he could come up to my room with me and literally professed his love for me. By the time we got to my building, I was ready to book it as fast as possible into the entrance door, which would lock behind me and he would be unable to enter without a key. This dude was literally screaming, ‘I love you, please let me in!!!’ as I politely but quickly went inside. I blocked him immediately.” — @Helpful_Finding78
8. “Thought I’d Convert to His Religion—After One Date”
“We were in our first year of college—we met in the library, and he seemed nice enough. But on our first date, he asked if I was Catholic. I said no—I wasn’t personally religious, but I had been raised as a Protestant. He said, ‘Okay, well, don’t worry. You can convert. I’ll talk to the priest on Sunday, and we’ll see what you need to do.’ That was that.” — Anonymous
9. “Had Me Drive Because of a DWI, Then Got Drunk on Our Date”
“I met this guy at a bar (yeah, I know—great start). We exchanged numbers, and the next day, he asked me on a date. When it came time, he told me I needed to pick him up because he lost his license for a DWI. We went to a restaurant, which was nice enough. He got two drinks there, and I got one. He asked if I wanted to go play pool somewhere else and get more drinks, and I agreed. While we played pool, he had three more drinks and watched a basketball game the whole time. We then went to a different bar, where he got five more drinks (I had maybe three drinks total by this time).” — Anonymous
“He got so drunk and proceeded to tell me all about our future wedding and the song we’ll dance to. I told him I needed to go, implying that he needed to wrap it up so I could take him home. He said I could go and that he’d find a ride. Two hours later, while I was in bed, he called me asking for a ride home. Against my better judgment, I picked him up and took him home. He was very drunk. Before he got out of the car, he kissed me very sloppily and told me he loved me. There wasn’t a second date.” — Anonymous
10. “Dismissed the Entire #MeToo Movement”
“I had a guy say that the #MeToo movement wasn’t real, and he didn’t believe women were actually harassed and assaulted as often as people claim. He said he used to be motivated to support women, but he’s never ‘heard locker room talk,’ so he doesn’t think it’s a real thing. He said women are missing out on a lot of really great guys because they’re so ‘over-sensitive’ and worried about assault, a thing that almost never happens. He also said that lesbians make him mad because women trust them more, and they’re ‘able to have sex on the first date.’” — @sarahshorthealth
11. “Left Me in a Dark Alley After Saying I Wasn’t His Type”
“I got set up on a blind date by a classmate. There was zero chemistry, and the guy barely spoke to me when I tried to ask questions/get a convo going. We finally left the coffee shop we were at and walked through a back alley to get to the parking lot. He turns to me and says, ‘I’m not gonna call you. We don’t have anything in common. [Our classmate] said you were cute, but…’ and he left me standing in the dark alley alone.” — @lamusica83
12. “He Wanted Me to Change My Hopes and Dreams—for Him”
“I had a guy ask me about my hopes and dreams. He then proceeded to tell me in great detail that I had to change all of them so that I could be in his life.” — @tonideenz
13. “Planned Heists with His Mom”
“He told me his mom would love me and bake me cookies while we robbed banks. When I decided to leave, he insisted on holding my hand as I walked out and tried to kiss me, but I dodged. He threw my hand at me and walked away with a loud scoff. I thank my lucky stars I wasn’t assaulted that night. The guy weighed easily twice as much as me and had such big muscles that some dude walking into the bar behind us said, ‘Damn, dude, I played college ball, and I haven’t seen calves that big.’ I had no idea that happened in real life, but his calves were truly massive.” — u/QueenNibbler
14. “Critiqued My Outfit, Then Tried to Get Me Into Bed”
“This guy thought I was really nice and smart. I actually had fun until he told me I couldn’t go on ‘dressing like this.’ I needed to wear ‘more feminine clothes’ or else I wouldn’t be seen as attractive (let alone be loved). But we’d still end up in bed together, so he’d keep in contact. Spoiler alert: we did NOT keep in contact and sleep together.” — @Joubachi
15. “Locked Me in His Car After Ripping a Massive Fart”
“I didn’t even get to the restaurant before he closed all the windows, locked them, then ripped ass worse than I ever heard before. I got out of the car at a red light and called my sister to pick me up.” — @Agitated-Mechanic602
16. “Left Me for His Dealer Mid-Movie”
“He left halfway through the movie to go meet his dealer. I finished the film, got pizza and wine, went home, and watched Buffy the Vampire Slayer by myself.” — @gracem485e511d7
17. “His Shed Was His Room”
“A guy picked me up on his motorcycle to take me back to his place. He pulled up to a shed by the house so I could get off, and he could store the bike, right? Wrong. The shed was his room (this could already be a horror story, but we’re talking worst date—not near-death experience). He invited me in where there was only one place to sit: a recliner, which he sat in. The only other place to sit was his lap, which he alerted me to. I chose a crate instead. He shared his airplane bottle of mouthwash-flavored vodka with me and, within maybe 15 minutes, said I looked like I wanted him to kiss me.” — u/jay8996
“What I wanted was to pee, so he took me to the house on the property (which was his mom’s). She was watching TV on the couch, and when I came out of the bathroom, he ushered me from the couch to sit and chat with his mom. Shortly after that, I used our initial agreement to request a ride back home. The next day, I texted something about feeling we were incompatible and wishing him well. He said, ‘Your loss.’” — u/jay8996
What’s the Craziest First Date You’ve Had?
These wild, awkward, and downright disturbing stories show that first dates can sometimes be total disasters. But they also make for the best stories—at least in hindsight! If you’ve ever had a date that left you saying “never again,” we want to hear about it! Drop your wildest first date stories in the comments below.
Share this article if you’ve ever been on a date that had you running for the hills!