Tellwut’s “Worst Date” Entries

Here’s some of the best (or worst?) horrible date stories that Tellwutter’s sent in! These are some of our favorites. We hope you have just as much fun reading them as we did!   My absolute worst date was when […]

Here’s some of the best (or worst?) horrible date stories that Tellwutter’s sent in! These are some of our favorites. We hope you have just as much fun reading them as we did!

 

My absolute worst date was when I went to the movie theatre with my GF. We were watching King Kong, a very long movie, when I had to go to the restroom. When I came back into that dark room, I sat down and a few minutes later I touched my GF’s leg but it felt a little weird and she started to look at me with her disgusted eyes. It was not my girlfriend!  I sat at the wrong seat. This was by far the most awkward moment of my life, but I still laugh when I think of it now.

 

Dude stopped at drug store for condoms and then asked me to stay the night….on our first (and last) date!

 

I was on a date with my fiancé. We had decided to go four-wheeling in his jeep. The jeep had a soft top (removable vinyl). We went “over the river and through the woods” to enjoy the ride (the jeep was four-wheel drive). As my fiancé got out of the vehicle to relieve himself, a pack of wild dogs ran up towards him out of nowhere. Needless to say he jumped into the jeep and sped off toward the main highway. As we approached a red-light I looked down to see that my fiancé had forgotten to place himself back into his pants due to his excitement over the pack of wild dogs. It was an extremely embarrassing and funny adventure.

 

It was pretty much my first date ever and it took place during my second year in college. This guy and I were supposed to go to a movie then onto an on-campus event afterwards. English was not his first language so throughout the entire movie he was asking questions loudly about it, annoying me and the people around us. He also laughed loudly at the funny parts, only a few seconds after they occurred and everyone else was at a light chuckle. The worst part came when we went to the event afterwards. We sat down at a table when suddenly he said he had to make a phone call, but would be back and that I should wait for him. I was there by myself for 3 hours. No text, no phone call, nothing to indicate he wasn’t coming back. Granted, I participated in a few activities by myself for awhile, but eventually I gave up and left. I even cried later because it was the first time I had ever been ditched by anyone and it wasn’t the best feeling in the world. His excuse was that he was on the phone for so long her forgot about me. Yeah, sure. I never spoke to him again after that.

 

I got engaged on Valentine’s Day 17 years ago and I should have said no then….

 

One of my friends was writing a card to her new boy friend. She was so sick of her previous boyfriend. I think because of that somehow she wrote her previous boyfriend’s name in the card for new boyfriend. The stores were all closed by that time and they have a date at 6:00 am on Valentine’s Day

 

I had been invited out to a romantic dinner and movie night concluded with a romantic night alone in a nice hotel. I was supposed to meet him at the restaurant. When I showed up at the restaurant he wasn’t finished working yet as he was the chef there. So I ate dinner alone. When he was finally done we went to the movies and I found out that he had invited a bunch of his friends and had his brother ask my sister/best friend out so that I had someone to talk to. So I shut up and watched the movie as he said we would be alone at the hotel. After the movie my sister and I went to the washroom and he said he would meet us outside. We went outside to find him and couldn’t find him. We waited ten minutes and he never showed up and we couldn’t find him. After my sister and I had to call our mom to come get us since he left us stranded at the movies, he had the nerve to text me and ask if I was still going to meet him at the hotel for our Valentine’s Day romantic night. I told him off and told everyone what he did and then broke up with him.

 

On my first date in high school my date shut the car door on my hand

 

I got dumped on Valentine’s Day at a wedding reception. my ex boyfriend stood up in front of 180 people and said ” I do not love you anymore” ” I have been cheating on you for over a year ” and I no longer need you in my life” . I was crushed he was my high school sweet heart, and we were engaged as well. At the time I thought that he was my world, my rock, my everything.

I went on a first date with someone I met on plentyoffish.com to a Mexican restaurant on Valentine’s Day about 6 years ago. The entire evening was awkward. We had nothing in common. I just wanted to finish my dinner and margarita and leave, so I drank the margarita as fast as I could without looking like the world’s biggest, sloppiest lush. Mind you, this was a margarita the size of a fishbowl. Once our check arrived, we got up to leave. Only I had been sitting on my leg the entire evening, so upon standing, I fell as soon as I put weight on my leg. Not only did I fall, but I hit my face on the tile floor, chipping my front tooth. not only did I chip my tooth falling face first on the tile floor, but the entire restaurant (which was insanely busy, naturally, on v-day) got a bird’s eye view of my nearly-bare backside when my dress flew up to the middle of my back. After being helped up, I realized how bad of an idea it was to have downed the entire margarita in such a short amount of time. I tripped and stumbled the whole way out of the restaurant to the vehicle. Once we left, I immediately realized I was going to be sick. And sick I was, all over the interior of his new BMW. Insult to injury does not even begin to cover the humiliation I felt. Needless to say, we have never seen each other since.

 

I went on a date and I was drinking too much. on the way home I asked my date to pull over because I was going to get sick , he refused so I opened the car door and another car was coming and almost hit me and my date said OMG what will I tell my wife? I had no idea he was married. :(!

 

I was asked to go out for dinner many years back by my old x boyfriend. He picks me up and said he needed gas so we get the gas and he said he forgot his credit card so I paid. While driving to dinner he let me know that he went to the flower shop and it was too busy so he walked out and he owes me one. When we got to the restaurant I ask do you have money to pay for dinner or is u going to let me know that you don’t have cash either. He said he didn’t have enough for both of us. I said take me home.

 

Went on a blind date just to find out that he was 6 inches shorter than I…yes, i know i should have asked. then went to dinner and he used a coupon, wanted a glass of wine so bad but he didn’t have enough money for that, I even offered to buy but he wouldn’t let me. The conversation was pretty much one sided and I was pulling teeth just to answer my own questions. I only thing he could think of am if he had enough gas to get home, so glad I drove.

 

One valentine’s day, I was single and I wanted to feel like I took out to dinner alone with a guy from high school that was ugly though, was very friendly. I said to go to dinner and an amusement park. Went to dinner at a Wendy’s! Just pay me a cheeseburger, a frosty and a soda! After the terrible dinner went to the amusement park and made me get on all machines. In the fourth ride vomited everything she ate and after so great shame went to the car and fell asleep! As I do not know how to drive the car, I had to call my dad and he gave me a big scolding! Carry in the car the boy to his home and halfway threw up in my dad’s car.

 

I went on a date a long time ago to the drive-in theater in an old rambler car. When my date asked me if I wanted to get into the back seat I replied “no thanks, I want to stay up here with you”!

 

My first real date as a teenager my mother insisted on going, she had said she would sit a few rows behind us in the theater she ended up sitting in between us and sharing our popcorn! Absolutely mortifying at 15!

 

I met this woman was seeing her for six months .did not know she was married .showed up at her front door with a box of candy, a dozen of roses, and a robin around my lower parts and pants around my ankles and her husband answered the door. Needles to say I had a bad valentine’s day

 

On my date with Kevin, we were out to dinner and we were having a normal conversation until he asked me what part of the body I thought was the hottest. I told him I thought it was the eyes, and I reflected the question right back at him. He told me to guess. I guessed eyes, mouth, face, and legs, and he told me that I was wrong, each time. I told him that I’d guess once more, and then he’d have to tell me. He agreed. I guessed the chest, and he told me that that wasn’t it, either. I then asked him to tell me, since he promised he would. He stood up, looked around at the sparsely-populated restaurant, then turned his back to me, pulled his pants down a little ways and showed me serious crack. Someone at another table said, “oh my god,” and Kevin hiked up his pants and sat back down. I had lost my appetite and could only look at him in disgust so I walked out. That’s the last time I ever saw him

 

Yes my date showed up in his mother’s car he had no teeth an I paid for the breakfast he also kept referring to himself as my man I became irritated an left

 

I went out with a guy to the movies… we did not go out for dinner first, so I was hoping for some popcorn and a soda at the theatre. On the way, he stopped at a gas station, said he would be back soon. He did not say what he was buying, I was holding out hope that it would be a snack for the movie. Well, we got to the theatre, took our seats just about in the middle of the place. I just knew that he would ask if I wanted popcorn & a soda. I noticed he still had the bag from the purchase he had made at the station. Well… if not popcorn, maybe some mom’s. The lights went down, the movie began… he opened the bag and pulled out… out a “grapefruit”. He peeled it with his fingers, sat there and ate it. You could smell the fruity scent all over the place. The guy with the flashlight was in the aisle looking puzzled like, “what is that smell?”, as he shone his flashlight around trying to figure out the odd scent. I slowly just lowered myself as far as I could in the seat. Nope, no popcorn/soda that night, not even a snitch of grapefruit. Before I went to a movie with another date, I asked to make sure we would be getting some popcorn!

 

My worst valentine was when a new girl came to my school, and everyone was like you two would be perfect! So on Valentine’s Day, I decided to ask her. But little did I know she was my cousin who transferred from a different school!

 

It was my first real date. I was 15, and my mom had set me up with a friend’s son. It started out well since he was cute and showed up with flowers. My mom had said his dad was taking us to a fancy dinner and a movie. 3 miles from my house the tire went flat on the truck so it took 30 minutes to get moving. Then we pull up for our “fancy” dinner at McDonald’s. Didn’t even dine in…Straight drive-thru. I tried to look past this since the flat tire had us running behind, but then our movie turned out to be a junior high basketball game at a school I was unfamiliar with. I figured we would head to my house so they could drop me off but ended up at their house where I was stuck watching tom and jerry with a 3 year old (who happened to bust my lip with a toy too) while my “date” played Nintendo in his room alone. I finally called my mom and begged her to come get me. She said she would be there in 10 minutes so I decided to wait outside. after a couple of minutes the boy came out to see what I was doing and dared me to climb on the dumpster with him, which was outside the pool fence. Always up for a challenge, I hopped right to the top without a problem. He soon followed and quickly proceeded to try to kiss me. When I resisted and backed away, I wound up going over the fence and into the pool full of freezing water and my gentleman of a date laughed until snot flew out of his nose!!! What a disaster…swore off dating until I was 16! (The up side of the night was that my mom had pulled up and ran to get me out of the pool and told the boy’s dad exactly where him and his son could go!!!

 

I met this guy and we went out to club in 2004 and we partied very hard I mean jello-shots dark liquor and light plus beer we partied it was the circle city classic after all. but when it came time to leave OMG we parked kind of far from the club, I said oh’ I have to pee he said just hold on we are almost at the car well be it as it may I fell and peed on myself in the middle of the street and he said you peed and I said no I didn’t while sitting in a paddle of urine.

 

I was on my first date with my crush. We were in a chic restaurant. We were about to kiss over the table, when my hair caught fire. Indeed, there was a candle on the table! My crush took his napkin and put it on my head. Fortunately, he had responded quickly and the fire had not done too much damage. I was so ashamed!

 

Worst date ever for me! I was so excited to finally go out with the guy I had a crush on for years. He finally asked me out. Picked me up on time. We stopped for gas. He left the truck in gear and it started rolling backwards. had to jump into the driver’s seat to stop it! We then went to dinner and then a dance. The night was awesome until I ran into a family member of mine who happens to pull me aside to tell me that this guy is my cousin! Date over!

 

I was on a date and when we went to her house, her “husband” came in and laid a .45 caliber pistol on the counter…exit stage left

 

Since we got married at a young age and my husband was in the navy and out to sea a lot when he was in port dates were a big deal. One date we had no babysitter so it involved all 5 kids and dinner. Some customers thought we were the “complimentary babysitter service” advertised for that night and started leaving their kids in our vicinity in the game room. Soon we had 30 kids and no idea who they were all begging for money for games and food!

 

We went to a romantic restaurant with fancy dress code. She went in a sleeveless dress and didn’t shave her armpits. Sufficient to say I was forever turned off.

 

I will never forget my worst date. I was in my 30′s, started dating this guy, who asked if I would join him at his parents’ house. They owned a farm. It was only like the 2nd or 3rd date, and it was on a holiday, Easter Sunday. I thought it might be fun to meet his family as I am a very social person, I like meeting new people. Well, lo and behold, after we were there for a bit, his parents told all of us that we had to help butcher chickens! I ended up plucking the feathers off of these birds! It was horrible, we were stuck doing that for 3 hrs. My clothes were filthy, I smelled bad, and after we were finished, I told my date that I need to go home, shower, and graciously told him I have a headache, want to spend the evening alone.

The worst thing is I have never gotten a date, so my mother took me out on Valentine’s Day

 

My name is my worst date ever was about 14 years ago but I had agreed to go out with a friend we were suppose to meet for drinks and then have dinner we knew each other through work for a while and this was supposed to be our first date excited about meeting him I arrived early but the date fell apart when I walked in to the bar/restaurant and saw him at the back corner table French kissing my mother

 

I had met this single mother online and had traveled over 100 miles to go on our first date on valentine’s weekend. I brought flowers and we had a pretty decent first date night. After getting home, we texted each other a bit before going to bed and she was complaining about pains and going to the hospital. After not hearing from her for a few days, I finally was told that she had gone into labor and had a new baby girl. Since it was cold that night we had both been wearing hoodies/baggy clothes and I had no idea she had been pregnant!

 

I woke up with a girl after a night at the bar and low and behold she only had three teeth and four of her fingers were missing!

 

Many years ago I was on a date with a guy who had a part time job delivering pizza. During our date his boss called him to deliver some pizzas so I spent our date with a stack of pizza’s on my lap. Worst part was when I got home that night I had a huge grease stain on my jeans that never came out.

 

When I was in high school I went on a valentines date and at the end of it we kissed. Unfortunately my date was sick but didn’t want to cancel because it was Valentine’s Day. At this point my date decided this was a great time to vomit and did it in my mouth. It’s been over 26 years and that horrible taste still lingers.

When my son was only five months old I found myself single again. A friend of mine hooked me up on a date with a co-worker of hers. The date didn’t go well this guy was all over me. I told him I wanted to go home and on the way he admitted the only reason he wanted to be with me is because he wanted to taste my breast milk!

 

Myself and my friend ordered a cake for our boyfriends last year from the same shop for Valentine’s Day. We swapped the cakes by mistake at my place. My guy bought me an expensive jewelry and with all the sexual tension in the air, I opened the cake package, and the astonished look on his face was what made me look down at the cake. The cake had my friend’s boyfriend’s name on it, and what made it worst was my friend’s boyfriend and I had a one night affair which only my boyfriend knew of. I was thoroughly embarrassed. Needless to say what followed was a whole lot of explanation rather than passionate love.

 

When I was 18, I went out with a boy I had just met and it was Valentine’s Day. He didn’t get me anything, which I didn’t really think of since we had just met. He took me to one of the cheapest, greasiest places in town to eat, then immediately drove to the lake and parked on a boat ramp where we were facing down into the water. He started to make moves on me and I didn’t even know him! I put his pickup in neutral and he was paying so much attention trying to get into my pants that he didn’t even notice that we had coasted down into the water until it started coming in at the doors. He never asked me out again.

 

Years before I was married, I went out on a blind date at Valentine’s Day. We met in a very small, quaint little restaurant, and we shared a bottle of wine, and had a full course dinner, plus dessert and a drink each. He seemed like a nice guy, and we got a long great. After dinner, just before the bill came, he excused himself and went to the restroom. The bill came and it was about $175, and I thought it was a little too expensive for a first date, so I decided I was going to split it with him. He took an unusually long time to return, so I asked the waiter about it. He said the “gentleman” had actually left, about 1o minutes ago. He told the waiter I was picking up the bill, plus he also took home a box of pastries which he added to the bill. so, not only did I get ditched on valentine’s day, I was stuck with the bill for dinner, plus for the dessert he would probably bring home and eat with his wife or who knows!! Then when I got out of the restaurant, I even had a parking ticket on my car! It was a disaster, but at least now I can laugh about it!

 

One valentine’s day, I romantically ordered a dozen red roses sent to my girlfriend at her office. The florist arranged them in a custom vase. As I anxiously greeted her when she came home from work, I noticed the empty flower vase. ‘Where are the roses?’ I asked. ‘Oh,’ she said, ‘I sold them to the guys in the office for $2 apiece.’ she didn’t even share the cash with me :(

 

My date was going to take me to the race track. I was all excited as I never went there. Well we drove up and he parked not near the entrance, but a hole in the fence where the horses were racing. We watched through the hole. That was the first and last date with him and the only time I was near a racetrack.

 

I went to see this girl at a restaurant and she was there at there before me. It looked like she was there for quite some time. When we finished and waiter brought in the bill which I volunteered and extended to pay, I found out she had 4 of her friends had dinner before meeting me and I ended up paying for 6 people in total shucks!!

 

I once went out with a girl who stole all the silverware and everything else from like four tables at the restaurant we went to when we went back to her place she had a room full of stuff she had stolen

 

For the afternoon date at a coffee shop, I dressed nicely but simply, arrived early and sat nervously at a table awaiting my date’s arrival. He arrived promptly on time and was just as gorgeous as his pictures. We exchanged greetings and chatted a bit about music, movies and books. We seemed to be meshing well intellectually and after an hour or so passed I was feeling a little hungry. I told him I was going to grab a bagel and offered to get him something as well, but he declined. When I got back to the table, he seemed a bit disturbed. Our easy banter of a few minutes ago was gone, and I awkwardly tried to resuscitate the conversation to no avail. Finally I asked him if something was wrong. I sat in complete disbelief as he told me how much he liked working out and being healthy and that he didn’t think he could be with someone that didn’t “respect herself enough to take care of her body.” he made it clear that he wasn’t attracted to women of my “size.” I was understandably confused (and fighting back tears) and asked him why he chose to meet me in public if that were the case, when he could have easily told me in a message. He replied that while he wasn’t interested in dating me, he was trying to start a personal training business. He thought I could be a customer and maybe after “tightening up a little” we could see what happened between us! I simply got up and walked out to my car and cried the whole way home. He kept texting for a while asking when I wanted to go “train,” but I never replied and he eventually stopped. I didn’t date for a year after that. What a jackass.

 

My 16 year old son told my date that he looked like a pervert. Specifically, Herbert from Family Guy and that he better not even think of sitting too close to me because I was completely out of his league. Once that pervert image was put into my head, I couldn’t stop laughing. We barely made it through dinner. My entire date lasted one hour.

 

11 Responses to “Tellwut’s “Worst Date” Entries”

  1. sarahr says:

    Gracious! It must have taken a load of wits and courage to get through some of these events. I try to imagine what my reaction would be under similar circumstances. Guess the adage is true: It takes all kinds …

  2. Karen DSouza says:

    I really enjoyed reading these. Some of them were hilarious !

  3. Karen DSouza says:

    Enjoyed reading these stories Hillarious !

  4. JT says:

    Reading these stories were pretty funny and interesting, especially the one with the awkward situation at the movies. But some I feel sorry for like the one that got her hand shut on the car door. overall they were nice to read =P. (Tellwut username- karat)

  5. Gloria says:

    The worse date I was started out ok, then he had a flat tire and didn’t have a spare or the money to fix the flat and I had to pay for it.

  6. adraine goins says:

    To be asked on a date, and your date gambles all night. No movie, no dinner. But when you get home there the sex!!

  7. Teri says:

    Oh man, these are hilarious and mortifying! Especially the personal trainer guy- what a jerk. I’m glad to say I don’t have any stories as bad as these. I think my worst date was when this guy took me out to a fancy jazz club and I felt so out of place. We were the youngest people there and everything on the menu was so expensive that we ordered spring rolls for dinner. I don’t even like jazz! -tpow518

  8. Melissa says:

    Hahaha! What a great and fun read.

  9. Beth says:

    These are hysterical, thanks for the smile. I’m glad I’m not the only one with such awful experiences!

  10. ashtuck2013 says:

    Some of these are hilarious!! Others are just terrible!! It’s interesting to see how ridiculous some people are… Hey T-wut I finished the Easter hunt! emailing you now! -ashtuck2013

  11. priscilla says:

    I enjoyed reading these stories. some of them were really funny. my username is priscynnov5

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