ADVERTISEMENT

What's the worst date you've ever been on?

NDallasRuss

HB Legend
Dec 5, 2002
37,082
34,685
113
I mean, excluding when you found out OP's mom was overbooked, or course...

For me, I once met a young lady and took her to a nightclub in Dallas for a little drinking and dancing. While there, she spotted an ex-boyfriend there with some other replacement girl, so she proceeds to get sh!t-faced drunk and tries fighting the both of them multiple times. I start trying to distance from her, because I don't need to get involved in all that, but security comes to me and tells me I've got to get her out of there. I got her out, got her home, and didn't follow up with her after that. Not long after, a friend he knew her told me she had herpes so, crisis averted on multiple levels.

Whatcha got?
 
First date and took a girl that I really liked to the movie "My Life" with Michael Keaton, might be the saddest movie I've ever seen. She's bawling, I'm bawling. Complete buzz kill. Never got a chance to take her out again after that.
 
I don't know that I've ever been on a HORRIBLE date but the one that pops put was a set up from friends and just had zero chemistry. She made me a nice meal and we hung out but it was like, thanks for the food, not, let's make out.
 
  • Like
Reactions: NDallasRuss
Not long after, a friend he knew her told me she had herpes so, crisis averted on multiple levels.
get-smart.gif
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
That girl takes loads to the face 100%. Assuming it was playful in the beginning, she was down with the jism.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
Bruh, she was definitely DTF and likely into butt stuff. You should have rolled with it.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
I just would have asked if I could leave one on her.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
Well, if you ever have a need for an alternative username on here it sounds like you've got one ready made.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
rorymiss.gif
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
 
Colleague/buddy and his wife set me up with his hs ex-gf and scheduled dinner double date. buddy and wife are ridiculously good looking, my expectations were accordingly very high. besides cold water on my expectations, combination of zero chemistry and massive awkwardness happened.
 
  • Like
Reactions: NDallasRuss
You very likely dodge a hot/crazy bullet but at 19 it might have been fun.
Maybe. I'm sure she turned out fine with a fine life. It just felt like when you're kind of interested in getting to know someone and they're only interested in tearing you down... I Just wasn't into it. Like I said, funny at first, but then she got mad when I tried to pivot away from it.
 
I took a girl out to Iowa Tap Room back in the Summer of 2021. Everything seemed to be going ok. The conversation was a little boring, but we got along fine. Then the food came, and she took maybe 3 bites of her meal. When the waiter came by to ask if we were done, she asked for a to-go box. She packed everything up, said thanks for dinner and for lunch tomorrow. I had already paid the bill and I wasn't going to ask for her half of the tab, but I knew I had been taken advantage of. That was the last time I took a girl out on a legit date for a first time meet up. Everything after that was either coffee or a drink someplace.
 
  • Like
Reactions: NDallasRuss
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.
She sounded funny as hell. I picture you being with this girl that night
Girl Interview GIF by SV Bergheim 1906
 
Maybe. I'm sure she turned out fine with a fine life. It just felt like when you're kind of interested in getting to know someone and they're only interested in tearing you down... I Just wasn't into it. Like I said, funny at first, but then she got mad when I tried to pivot away from it.
Pic?
 
I was talking to a girl, we had gone out once or twice.

We worked for the same company, different offices. We were messaging during the day, and I said let’s ditch work and get lunch then go to the zoo. She said “oh that’s sounds awesome”. I left work, went to lunch spot, she wasn’t there. Messaged her and she said she thought I was kidding.

Best I got outside of date getting drunk and puking in my buddies front yard.
 
  • Like
Reactions: NDallasRuss
My wife and I had gone on like 3-4 dates, and we were ****ing like rabbits when in the same city—both working professionals, I was in Miami and she in DC—so we decided it was time to go on a weekend trip down to key west.

We never argued once, but it was a train wreck. We were really young, mid 20s. We did some blow and partied on Duval night 1. Fell asleep on the beach day 2 and both got fried. Blister fried. It was like 77 deg, breezy, and slight cloud cover. Never felt a thing until it was too late.

Our guesthouse room was a cool lofted pool house. Only issue was the bathroom was just in the corner, just a knewall with a half saloon style swinging door.

She gets really sick from the burns. Starts throwing up. I have to go to pharmacy to get stuff, get her some soup. Play mister nurse. We get to sleep late. I wake up to her in the “bathroom” with diarrhea, like 6’ from my head—so I got up and went and slept on a pool lounger.

She was terribly embarrassed the next morning and sheepish. I told her not to worry about it, it would be a story we would always remember. I got my D sucked before we checked out. Drive back to Miami was long and not much was said because she slept the whole way.

Been together nearly 20 years since then—married on that island. I took my kids by that guesthouse last month when giving them a nostalgia tour, and sadly, that pool house was torn down and replaced.
 
First date and took a girl that I really liked to the movie "My Life" with Michael Keaton, might be the saddest movie I've ever seen. She's bawling, I'm bawling. Complete buzz kill. Never got a chance to take her out again after that.
Oh man, yeah, that movie wasn't putting her in the mood for sexy time at all!
 
  • Like
Reactions: beanerhawk
My wife and I had gone on like 3-4 dates, and we were ****ing like rabbits when in the same city—both working professionals, I was in Miami and she in DC—so we decided it was time to go on a weekend trip down to key west.

We never argued once, but it was a train wreck. We were really young, mid 20s. We did some blow and partied on Duval night 1. Fell asleep on the beach day 2 and both got fried. Blister fried. It was like 77 deg, breezy, and slight cloud cover. Never felt a thing until it was too late.

Our guesthouse room was a cool lofted pool house. Only issue was the bathroom was just in the corner, just a knewall with a half saloon style swinging door.

She gets really sick from the burns. Starts throwing up. I have to go to pharmacy to get stuff, get her some soup. Play mister nurse. We get to sleep late. I wake up to her in the “bathroom” with diarrhea, like 6’ from my head—so I got up and went and slept on a pool lounger.

She was terribly embarrassed the next morning and sheepish. I told her not to worry about it, it would be a story we would always remember. I got my D sucked before we checked out. Drive back to Miami was long and not much was said because she slept the whole way.

Been together nearly 20 years since then—married on that island. I took my kids by that guesthouse last month when giving them a nostalgia tour, and sadly, that pool house was torn down and replaced.
TL;DR version- OP got cock burn.
 
Asked a mutual friend to go to a Who concert with me as I had an extra ticket anyway. I wasn’t even really attracted to her but she accepted. She sat at the concert like a statue and later lost her damn mind when a joint got passed around in our seating area, a total Karen moment for her and I suddenly realized there were at least 20 other people I knew that I’d rather have sitting next to me at the moment. After that fiasco I don’t think I ever spoke to her again, except in passing.
 
Sometime between my senior year in HS and freshman year in college I took a girl to a black light mini golf place. The detergent from my clothes washer showed up weird all over my shorts and she kept saying it looked like a cum stain, which was funny at first. Then she started calling me cum stain. "Did you see that, cum stain?" "I got a hole in one, cum stain!" Then she was mad that I asked her to stop calling me cum stain. Then got mad when I told her I wasn't really interested in going on a 2nd date.

Can't take a hint huh?...
 
Back during my heavy drinking days after college I was a local at a bar outside of DC. So much so that if I didn't show up on a Saturday night they'd call my house and ask me where I was.
Anyway, one night my roommate told me that some girls from his office were going to meet us at the bar. I was immediately suspicious as my roommate had ZERO game. Anyway, get to the bar and the girls show up and the one 'for me' was a little pudgy and was wearing black and white zebra cowboy boots. Ugh. Anyway, we start to drink and I start to care less about the boots and the pudge. A few hours later she's all over me at the bar. I get up to piss and as I'm coming back from the bathroom the bartender stops me and say 'dude, no.' I'm like 'really?' and he's "No, absolutely not.' I thank him and head back down the bar to our party to find that she has puked directly on the bar and passed out. ON THE BAR. I turn back to the bartender and he says "get that fuking beast out of my bar." I apologize and we drag her out back while her friend gets the car. We dump her in and they drive off. I go back in and have another drink. The next monday my shitty wingman roommate says she wants my number. I tell him to fuk off.
 
People be like "DoN't StIcK yOuR dIcK iN cRaZy" and then sit around and rag on people for not trying to **** someone they're not into and getting red flags from.
I firmly disagree with not sticking your dick in crazy. Crazy is fun, until the explosives start discharging, then you disengage.

The phrase should be “never commit to crazy”

But I feel you. Big difference between some sexy broad teasing about cum stains and some awkward cum stain jokes from some 5 with no sex appeal.
 
  • Like
Reactions: millah_22
Went on a date with a girl I knew after my divorce. Very pretty, kind, fun to be around, easy to talk to. We went to a brewery and had 2 beers in maybe two hours. A friend was at a bar close by and asked us to come join them. We walked in, I grabbed a beer and went to their table to say hi.

Well, buddy was drunk AF and after a few minutes he thought I was talking shit about his wife. I had recently torn my biceps tendon, labrum, and rotator. Any my buddy, without provocation, shoves my as hard as he can and knocks my on the ground behind the bar. My shoulder was ****ed and I had to be helped up. She was mortified, buddy got kicked out, and I went home alone. Ashly hasn’t talked to me since.

/csb
 
  • Wow
Reactions: millah_22
ADVERTISEMENT

Latest posts

ADVERTISEMENT