30 First Dates So WTF Lucifer Himself Would Cringe

1.

First date with a guy I met on a dating app. I sat down and he immediately was like "Oh yes, you are hotter than your pictures and you're my girlfriend now." Came on real strong. I chalked it up to keenness at first (maybe a weird sense of humor?) and figured I'd at least stick around for a drink or two, feel it out. Even offered to buy the first round, partly as an excuse to get away from the table for a second.

I made some unrelated comment to the bartender that made him laugh, and when I got back to the table, dude LOST HIS S**T. Wanted to know what I said, whether I thought the bartender was good-looking... Had somehow gotten insta-jealous of this bartender five minutes after meeting me. There was no second drink.

2.

I took a shot at asking this girl out from down the hall in my apartment. She says yes and we go out to dinner. Right off the bat we learn that we have a mutual connection, a coworker of mine was her best friend - ok, cool. I order up a martini, she awkwardly orders a rum and coke. It was at that point I realized she either doesn't drink often, or she drinks way too often (who orders a rum an coke to go with dinner?). Anyways, two drinks in she starts telling me how she has conversations with her dead dog and how her dead father sends her text messages. Then, she informs me that she is heavily medicated and those meds shouldn't be mixed with alcohol.

Another 10 mins later after I try to get her to drink some water, she is trying to pick food from the other tables plates and her boob is hanging out. Straight dangling. I try to help her out of the restaurant to get her home, some chads think I'm trying to take advantage of her so now I'm dealing with that. She ends up calling her friend and my coworker while I'm busy getting her a cab and tells my coworker that I got her drunk while she was on her meds (she is getting emotional now that she realizes I'm sending her home). Before she leaves she pukes down the back side of my shirt. I just bought that shirt that day.

I ended up meeting my now wife at the bar that night while I was trying to drink off the memories of what just occured. She thought it was weird that I had on a white undershirt, my pants were wet and I was holding a button down shirt. To this day she still laughs at the stupid situations I get into.

3.

Showing her a video on my phone and my boy texts me "did you f**k her yet" and it pops up on the screen.

4.

Dating app, smallish town Kingston Ontario. Go on a few boring dates. Cue story. Match with girl, she agrees to meet but there was something odd about the conversation. She was eager to meet, suspiciously eager. I get to the Starbucks and wait inside for 20 minutes past the agreed meet time. Girl texts me says she running late, asks me to stand outside so she can see me as she drives by.

I look over and theres another dude standing on the sidewalk with his phone in his hand. Recognize him from the gym, ask if hes also meeting a girl, and what her name is. Turns out the girl was pulling a fast one on us both as revenge for her girlfriend who we both apparently dated once and didn’t like. So him and I went to get ice-cream together and sent her a photo of us having a great time. Wish I still had the photo!

5.

I went out for dinner and a movie with a guy. I tried to chip in money at both, but he insisted that he cover it all. At the end of the night, we're sitting in his car in the parking lot of the restaurant we had just eaten at, and he asks for a BJ saying "I mean, I bought you dinner and took you to a movie, it's the least you can do". Thankfully I lived nearby, I hopped out and walked home.

6.

Met a girl on Craigslist (this was a long time ago obviously). After a few messages we set up a date at a bar downtown. I show up and she's already there with a guy friend. No biggie I'm thinking, she's just playing it safe. They are at a two person table and the place is packed. They already have drinks so I grab one for myself and put it on my tab.

Her and her friend proceed to ignore me. Like I say something and neither one acknowledges anything unless I ask a direct question. Even then I get one word answers with attitude. So I finish my beer pay my bill and leave without saying a word. Later I get a barrage of messages about how I'm a [jerk] for sticking them with their own tab.

7.

I agreed to go on a date with an older coworker from my first job at a supermarket, I was 20 he was 27. He took me to lunch and didn’t let me order for myself; when the waitress came to ask what I wanted to drink he cut me off and placed both my drink and food order (I hadn’t even glanced at the menu yet).

He proceeded by saying I needed to meet his mom and brother soon and how we should get married and eventually have kids. Mind you he didn’t know a single thing about me.. I quit shortly after that and he would message me on social media every now and then saying things like my then boyfriend didn’t deserve me until I blocked him everywhere.

8.

Well.. I had a crush on this guy in high school and my friend kept urging me to talk to him. I got the nerve to and apparently he liked me too, or so I thought. We talked often and exchanged notes in the hallway. He asked me to homecoming and I said yes. I was so excited. Bought a new dress and everything!! Got to the football game and met up with my friend. I finally saw my crush and told him I was gonna go sit with him for the game.

He’s like “no, you can’t”. I’m like “why?” Him: “Because I’m with my girlfriend!” I was devastated and embarrassed to say the least. Didn’t stay for the rest of game or homecoming. Called my dad and he picked me up in front of the school where I was sitting all by myself.

9.

My wife wanted to plan our 13th wedding anniversary. I was excited because usually I plan it. She bought us some new disc golf discs and after a quick supper we went to play. We hadn't played in forever. We were laughing and I had a great time. She served me with divorce papers and told me that date was a test to see if she still had feelings for me. I also learned that she was having an affair that started well before our anniversary.

10.

I went on an online date with this guy when I first moved back home from college...

We met up and I have a habit of telling my parent "i'm going out, I'll be back later" w/o specifics, etc. Anyway, this time, she says "just be careful and if he can't drive, get out the car."

We were en route to our first destination and it was closed. So, he asked me where I wanted to go and I said, "Hooters and bowling." I know, keep it classy right here.

His driving was so reckless... I mean, REALLY bad. Anyway, we ended up going across town because he wanted to take me to this one place. By this time I've determined I'm not into him and I want out, so I just go along with it, maybe we can be friends, right?

His breaks give out and we end up having an accident. We ran into the back of a truck pretty hard and I jerk forward, glasses flying off. After the smoke settles, when I'm nervous, I start laughing. He asks if I'm okay, I said sure and I'm looking for my glasses and he goes, "oh this is bad, really bad." So, I said "Why? No insurance?" He says, No, I have a warrant for my arrest He gets out the car and runs. As he's running into the sunset, he's yelling back at me "i'm really sorry, I can't afford to go to jail again."

The person we hit, leaves. So, I'm the only one there and police show up. I had to call my parent to come pick me up because I have no friends in the area and of course, I gave the cops his info. I knew I wasn't going to talk to him again. The police gave me a ride to a gas station across the street as I was waiting for someone to pick me up. I leaned back, took a picture in the cop car, posted it on Facebook and tagged him in the picture. Somewhere in between the running he found time to get on Facebook and block me.

Bad part about not just the accident, I didn't even get a chance to enjoy Hooters and wings.

11.

Went out with a girl I met on a dating site. We met for coffee, got our drinks, sat down…..and she forgot how to talk.

For almost an hour, I would try to start a conversation and bring up any and all topics I could think of. I tried talking about our jobs, hobbies, families, anything really. Her responses were just “Uh huh”, Oh yeah”, “That’s cool” and “Nice.”

She wasn’t looking at her cell phone, looking out the window or being distracted. Completely forgot how to have a conversation while staring at me for the hour we were at the coffee shop.

It was the shortest and longest date I’ve ever experienced. After leaving, I hit the McDonalds drive thru and had a consolation meal to put that bad date behind me.

12.

My rule was first time meeting someone was usually at a coffee shop or something similar. Some intimate setting to get to know the person better.

Met a girl on Tinder. She seemed very nice and somehow we had a good bit in common, other than she was religious while I am not. She never brought it up in conversation so I didnt think much of it.

Decided to meet her at a Starbucks halfway between our homes. She was nice, but seemed nervous. Thought it was the first date nerves or something. Probably about 15 minutes into talking, another dude who was sitting a few tables near us comes to sit down right next to her. He pulls out a pamphlet with the words like Jesus and Are you lost? written across the top. I'm super confused at this point. I tell the guy "No thanks" and that we didn't have time to hear about it. SHE then begins to tell me that this was her friend and that they wanted to talk to me about where I was in life and how Jesus can help.

I think she mentioned something about how today's youth is being corrupted by online dating and how we're straying from God's light. Realized then that I was in a religious interventiom. I was pretty freaked out. I think all I said was something to the effect of "This is [messed] up," then stood up and left. She texted me later to tell me that she was there for me when I was ready to hear God's word.

13.

Went on a date with a guy who seemed really cool. He used to race bikes until he landed on his head after attempting a jump.

During the date he:

Told everyone we were on a date. Everyone.

Told me he wanted to kill his ex roommates.

Asked the waitress to make the date more romantic, so she brought out a giant ice cream sundae (meant for 2 people to share). He ate it all by himself, and spilled ice cream all over himself.

Bragged about beating the world record for the jump on which he landed on his head.

Kept asking me if I was a gold digger, because he makes tons of money and needs to protect himself.

Demanded separate bills (no big deal).

All 4 of his credit cards were declined. Asked me if I didn't mind paying and he would get it next time. (not that there would BE a next time ever)

Told everyone that the date went "splendidly".

Gave me stickers to his welding company as a thank you for paying since his credit cards must have some kind of error.

14.

I was on a first date with a girl I had met through doing some community theatre. We'd gone to the movies to see "Cloudy With A Chance Of Meatballs." Before the movie, we were chatting and slowly realizing that it definitely wasn't meant to work out. We just had too many conflicting interests and opinions. It made the experience incredibly uncomfortable, especially because we started lightly arguing over things like politics and religion. I was young and I was an idiot.

Anywho, before the movie started I texted another friend of mine to tell her (the friend) how terribly the date was going. And then I heard that fateful sound. Immediately after clicking "send" on my phone, my date's phone chimed. She pulled it out of her purse and read whatever text had come in. She then slowly turned to me and asked...

"Did you MEAN to send that to me?"

I immediately realized and explained that I had just opened up whatever the most recent message in my inbox was and replied to that, with the intention of texting my friend. Or perhaps I'd clicked the wrong name in my contacts list (they both were the only names beginning with M in my phone.) Needless to say, she was pretty upset.

I explained that, despite our differences I really enjoyed her company. I really did, because she was brilliant and beautiful. Certainly out of my league. So we continued the date as friends which was more awkward than we had anticipated.

After the movie, we went our separate ways. When I got back to my apartment, I texted that same friend again about how that date was incredibly uncomfortable and I doubted that there would be a follow up.

My phone chimes.

"You sent it to me again."

15.

Years back, in my early twenties, I met this girl online. She seemed nice, geeky, into a lot of the same nerd stuff I was. Cute in her photos too. She dodged me several times about going on an actual date, but finally we set something up. She wanted me to come to her house so she could make dinner, watch a movie; we were both introverts, so that's fine by me.

She said she lived in Houston, but it was actually over an hour outside of it (Which isn't crazy because Houston is yuuuuge). When I got to her 'house' it was actually a trailer in the middle of the woods on a wooded lot full of trash. Turns out they didn't have a trash service, so she basically just threw it outside. I saw cats everywhere, but... It was cats and giant freaking rats.

Still, I'd driven an hour plus, and I was already there, so I climbed up the decrepit deck and knocked on the door. When she opened it, the smell of cat urine poured out of the trailer and invaded my nostrils just as roughly as the Nazis did France.

I get inside.. Cats everywhere. Orange vats, brown cats. Skinny cats, fat cats. Old cats, young cats. Cats everywhere. I knew she lived with her mom, and I got to meet her. She was huge, like.. HUGE. I don't know how the trailer floor held up, and when she got close to me, she smelled like straight up ammonia.

The mom was "cooking dinner" for us, which was like precooked frozen stuff. The girl drug me to her room and attacked me like an animal in heat. I begged off to go to the restroom and the room was covered in cat [poop] and litter. Just box after box, the shower and everything. I couldn't do it.

I went and told her Id forgotten the flowers in my car and drove the f**k away as fast as I could.

16.

I finally took a girl out I had been pining after for a long time.

She had been in a bad relationship for about two years, had a kid with the guy, and they finally broke up. I waited a few weeks, and asked her out. She agreed. I picked her up with a teddy bear holding some flowers, she loved them and put them in water immediately.

We went to a local sushi place, ate our fill and headed out for a movie. Watched the whole movie together in the theater, flirting and touching the whole time. Afterwards, we went driving around and just talked for about two hours before I took her home. We made out on her front steps for probably 20 minutes before we finally peeled ourselves away from each other. I went to bed feeling absolutely fantastic.

Woke up the next day and texted her good morning. No reply. Whatever, she had a baby. Figured she was busy. Went about my day. Finally got in Facebook during my lunch break and she was back together with her ex already. Haven't talked to her since.

17.

I've got a couple:

Meet a guy from OKCupid. He seems nice, but never stops talking. After interrupting me for the 3rd or 4th time, I finally ask him "do you want to hear anything I have to say?" He apologizes profusely, says "you're right, I'm so sorry!" and pulls out a pad of paper and a pen. He then jots notes as I'm telling him about myself and whatnot. I finally ask him what he's doing and he says "oh, I'm writing down things I want to tell you when it's my turn to talk again."

Met another guy from OKC. He knowingly used pictures that didn't accurately reflect the way he looked and kept saying "you look just like your pics!" in shock. He then told me I reminded him of his mother... Like it was a good thing.

18.

Tinder date. She looked nothing like her picture while not ugly just completely different. Picked the worst restaurant in town which I looked past because everyone has different tastes. We came back to my house and complained about not showing affection or touching her so I started touching her and then got mad about it.

She wanted a hook up which I didn’t, but the final straw was when she decided she didn’t like my house which I had just bought and was Proud of. she immediately wanted to go to home depot to buy stuff to start remodeling. It was by far my worst and the weirdest date and I hope she found a house to remodel.

19.

She started talking about her lifestory from childhood to that day. Year by year.. with every single traumatic story and emotions. That was our first ever date and she didn’t even let me speak for that duration. I was like “oh okay she is now talking about highschool 6 more years left, hold tight”

20.

I went on a date with a girl in college, a cutie from my class who I had been trying to get to agree to the date for a while. So I picked her up to drive to dinner, and it is worth mentioning I lived in Wisconsin and it was January so like -23 outside. Turns out she was bipolar but refused to take any medication for it so she had a manic episode while we were driving, proceeded to undo her belt, open the door, leap out of the car into a snowbank, and started running into the woods.

I had to chase her down and convince her to get back in the car with me before she lost her feet to frostbite. We didn't date anymore but I was able to convince her to start her meds and keep on them through all of college, she's actually a pretty successful software engineer now.

Unrelated but that is one of three times a date ended with me in a snowbank on a subzero night.

21.

It was with a guy who had recently been broken up with. We were already friends so we went to his house to watch a movie/play video games. Right off the bat he lays on the couch goes on his phone, I have nowhere to sit and end up on the floor. He then opens his exes facebook page and proceeds to show me pictures of her. When he was done doing that he fell asleep. I had didn't have a car at the time so I called a ride and played his Xbox while I waited.

Did not have a second date.

22.

I went on a Tinder date with a guy who is now in my contacts as "Donotanswer Penispic."

Prior to the date he seemed normal. We texted and talked on the phone then arranged to meet at a restaurant/bar.

He was cute but definitely bitter about something. He was from California and apparently didn't like this new city we were in. He started talking about sex and blow jobs and complaining about how uptight everyone here is about sex.

He invited the waitress to a party his company was throwing, after sending back the French fries he ordered.

I showed him a picture of my dog on my phone; he took out his phone and showed me a picture of his penis.

We walked out of the restaurant together to get our cars from the valet. My car came first and I left. He texted me later that he had my sweater (apparently I dropped it on the way out) and if I wanted to see it again I'd have to hang out with him.

RIP, sweater.

23.

Uh…

My best friend set me up on a blind date straight after my divorce. I was 22(yes, 22 and divorced), and she told me I “needed a good man”. She told me all about how this guy had a good job and he was sooo nice blah, blah, blah. She would NOT tell me how old he was, and would only send me blurry pictures. I felt pressured so I went.

He was no where near as attractive as she had made him out to be, and much, much older than I expected. He looked at me and said, “she didn’t tell you how old I was, did she?”

Anyway, this guy proceeds to drive me around his property, which is huge and beautiful out in the country in TN. He takes me up on a mountain on a four wheeler and proceeds to try to kiss me. I, being terrified I might be murdered out here in the middle of nowhere(he had brought a gun along), let him and it was one of the worst kisses I have ever had. He then took me down off of the mountain to shoot and critiqued my form the entire time. Then he proceeded to absolutely trash his ex wife because she turned out to be a lesbian while walking me around the house they lived in and showing me all of her favorite places and telling me all the things she would do there.

He then showed me the house he was living in with his brother which was basically just a shack.

It was awful. I now tell everyone she tries to set up about this experience, and let them know not to trust her.

24.

Met a lovely girl over Tinder, we really hit it off and had a great conversation, decided to meet in person for coffee the next day. She showed up on time, looked just like her pictures - and brought her boyfriend.

25.

Met a girl at a country bar one night in my 20s. We were both pretty drunk but hit it off pretty good. Ended up getting her number and we agreed we’d go on a real date. Fast forward to the date, she gets in my vehicle and…… she looks almost identical to my mom. I was mortified. I was polite and we went for lunch where I found out she also had a boyfriend she “wasn’t sure if she was into”. Never talked to her again.

26.

She ordered a steak to go, then sat quietly and waited for me to finish eating. She didn't want to answer questions, and didn't have anything she wanted to talk to me about. "see you later," she said as I dropped her off. "Not likely." I answered.

27.

Started fine with a decent dinner. One hour later she grabs me by the neck, looks me in the eye, and says “I want you to get me pregnant.”

Feeling completely uncomfortable, I said maybe it’s best we call it a night. On the way home, she starts screaming and yelling, then undid her seatbelt and began kicking the [hell] out of me while I was driving her home.

Pulled over, called the police, they came pretty quickly and fortunately took her home. Apparently, she was on some kind of drugs and they kicked in right when dinner ended.

What a night.

28.

It was a date that wasn't. I put an personal ad in the paper (this was back in the day) and agreed to meet this guy at a certain place. He took one look at me and drove away. He never said a word to me, just look at me and left. I was very upset when this happened. I guess he didn't like the way I look.

29.

Met a girl through a dating site and we agreed to meet up for dinner. I learned very quickly that this girl had absolutely no sense of humor whatsoever. I don't even think she cracked a smile the entire night. The date just got more and more painful as the night went on. At one point, we were talking about online dating. She told me about a friend of hers that went out on a first date with a guy online. She said this crazy guy fell absolutely in love with her friend and said he wanted to marry her. So I said "Oh, well, I guess I shouldn't have picked up this engagement ring on the way here, then!" She just stared at me blankly and said "That's not funny."

Yes, it is. F**k you.

30.

Pulled out her phone and started playing clash of clans.