There isn’t much out there more humorous than my train wreck dating stories! My friends get quite the kick out of these gems, so I figured, why not share the entertainment?! There’s a reason (or 8) for why I hated dating so much…
The “That don’t impress me much” guy.
At the ripe age of 20 years old, a Facebook friend request from an old family friend sparked my interest because this guy was F-I-N-E! Being young and dumb and completely unaware of my own attractiveness, I was at a loss as to why he was interested in me, since he could clearly have anyone he wanted (confident much, Brooke?).
I hadn’t seen this guy in years and the last time that I saw him, he was a chunky 10 year old that my dad forced me to hang out with while our dads hung out together. I would reluctantly play with him, completely uninterested because, duh, he was a boy.
Flash forward about 10 years and he was no longer chunky and I was no longer uninterested. We talked through messenger a little and I was so impressed with what he was saying! He was a former college football player who had injured himself and couldn’t play anymore, but that was okay because he was already planning to go to med school. THAT’S WHAT I’M TALKING ABOUT!
So, I was so excited to go on a first date with him. So full of hope and expectations. Particularly, the expectation to eat on this date.
He had picked the location (a winery), that had a ton of things to do and was about an hour and a half away from where I lived. We met up, rode there together and I was STARVING. I purposely didn’t eat before we left, assuming we would eat while we were there. But, after picking pumpkins and checking everything out, I finally asked about eating and he told me that he wasn’t hungry.
Well, this is awkward.
Hey dude, this isn’t all about you! The other person on the date is fixing to take a bite out of this cute little pumpkin that we just spent over an hour “picking” following the hour and a half drive it took to get there.
But, he literally didn’t even think to ask about me. We spent the rest of the day doing what he wanted to do, while I contemplated sneaking a jar of strawberry preserves out of the gift shop and eating it in the bathroom.
But, I soon realized that set the tone for this guy. We spent the entire date talking about him- his goals, his dreams, his talents. The fact that everyone thought it was so strange that he loves salads because he’s such a big (read: strong) guy!!
So interesting! Tell me more!
After a few weeks, numerous phone calls, hanging out a couple of times, I finally realized that as fine as this guy was, I couldn’t stand to be around him. I’m not sure if he ever asked a single question about me after our first catch-up talk. It was all about him. But, I was too nice to break it off with him and soon enough he stopped calling and I didn’t try to call him either.
Flash forward a few years later, and I saw him at a local festival. Since we never got serious and there wasn’t any hard feelings (it just kinda fizzled out quickly), I waved to him and tried to have the “hey, how are you?” conversation with him, where he was blatantly uninterested and rude and ended it quickly.
Whatever, dude. I was just being nice.
P.S. You don’t impress me much.
The Best Valentine’s Date
I hope you already sense the heavy sarcasm in this one because it’s a great one!
I was around 18 and I had been dating this guy for almost a year when our first Valentine’s Day together rolled around. My best friend was actually dating his brother, and when I got to his house that day, he’d already given my friend her presents: a beautiful bouquet of flowers in a vase, a piece of jewelry, a sweet card, etc. He had obviously put a lot of effort into her gift.
My boyfriend wasn’t home from work just yet, so I was pretty excited to see what he had planned. I’d spent the last week making his present and I was hoping our plans to go out to dinner that night would revive our dying relationship.
He’d previously been great at gift giving (because he’d ask his sister what to get), but this holiday it seems he didn’t really care. He got in from work, and called me into his room. There was a couple of piles of clean, folded laundry sitting on his bed and he started off by handing me a wilting, thorny, bunch of roses wrapped in plastic. A thorn actually pricked my finger as I accepted them with a forced smile.
(Now, don’t jump down my throat here- the guy made good money, so it’s not as if he couldn’t afford a decent bouquet of roses, it’s just that he did a last minute dash on his way home from work and that’s all that was left at Wal-Mart.)
But, the roses were actually the best part! Because what followed the roses was a series of gifts “wrapped” up in his folded up laundry.
Item #1: A giant bag of candy wrapped up in one of his signature navy blue t-shirts.
Okay. This is a first.
Dear God, let it be the last.
Item #2: A singing, dancing Scooby-Doo toy holding a heart, wrapped up in a long sleeve t-shirt.
I don’t even like Scooby-doo?
I think this was supposed to be for a kid?
What is happening?
Why didn’t he get a gift bag?
Item #3: Another random bag of candy folded in another piece of laundry.
Slightly irritated over the fact that he obviously grabbed a few random things on his way home from work, I thanked him and hoped that our planned date would go much better.
But, this guy was a homebody who never wanted to go out and when he did, he only wanted to go to 1 place- Longhorn Steakhouse.
Now, don’t get me wrong- Longhorn is great! But, after a year of only eating out there, I was a little burned out. Not to mention, I hadn’t been very subtle in my desire to go to the Cheesecake Factory- somewhere I’d wanted to go because I’d never been. I thought Valentine’s Day would be a great day to try it out and he knew this.
In fact, he alluded to the fact that we were going by smiling when I’d ask where we were going and being vague.
So, when he passed up the Longhorn exit and got off on the exit right next to the Cheesecake Factory, I was pretty excited. Finally, he was doing something thoughtful for me. Maybe this wasn’t the beginning of the end of our relationship, after all.
But he damn near peed his pants when he took a right turn off of the exit instead of a left- where the Cheesecake Factory was. And he laughed hysterically when we pulled into the Longhorn parking lot.
He psyched me out and thought it was hilarious.
What a catch.
It was him or the dog.
Are you surprised that I have another story about the Cheesecake Factory guy??! You shouldn’t be.
Valentine’s Day was the beginning of the end, but like most of my relationships, I hesitated to just end it. I was hopeful things would turn around and I’d spent so much time with him already- time which included not going to the college of my choice in Lexington, and, instead, staying in our hometown and going to hair school.
I was that girl that stayed for the guy.
But this guy had no desire to move out of his parents’ basement- something that bugged me a lot. I was 19 and ready to move forward with my life. I wanted to get our own place together but he wasn’t interested in moving out at all. In fact, his plan was to buy the hill right next to his parents’ house and build a house there one day.
Hell to the no.
I am not living right next door to his parents house.
I suggested looking at places just 10 minutes away, but he didn’t want to move away “that far.”
This isn’t going to work.
So, I didn’t wait on him. When I finally realized that he wasn’t going to budge, I went out and got my own apartment in the city.
I should note that this guy was the opposite of a city guy and he hated it.
But, ya know what? I gave him the option of picking something with me and he wouldn’t budge. So, for once, I did what was best for me and got a place close to my work and school.
He was not happy.
He told me that I was stupid. He told me that he’d never come stay with me.
My most favorite thing that he ever told me was, “You know what your problem is?? You don’t listen!”
I knew it was over then.
He did end up (reluctantly) staying with me the first night in my apartment, but after that, it was months before he finally agreed to stay with me again.
Just to recap- your 19 year old girlfriend has her own apartment with no parents around and you’d rather stay at home in your parents basement?
Really, really weird.
But, he stayed with me again and it ended up being the nail in the coffin.
A few months before I got my apartment, he had given me a Shih-tzu for my birthday present. It was really nice of him and I loved that little dog (even though I had wanted a Yorkie, but, it’s the thought that counts right? I feel like that was very symbolic of our relationship).
Most people are aware that small dogs don’t make great outdoor pets, so I was so irritated when he would criticize me for having a dog inside my apartment.
Where was I supposed to put her?
Why did he buy me a dog if he hated dogs so much?
I just wanted to ask him if he was f*%!> with me?!
So, since she was a little dog, she also slept in my bed with me and he was NOT having it. She actually slept at the end of my bed between my feet, and when I explained this to him, he didn’t care. He demanded that she sleep on the floor. I tired to make her get down but she just jumped right back up there and for about 10 minutes, he refused to get in the bed. When he finally did, he rolled over with his back to me and refused to talk to me.
I was fuming.
This had to be the stupidest fight that I’d ever been in. I laid there for a few minutes and then decided that I’d finally had enough.
I told him to leave.
He told me that if he left he would never come back.
And I told him that was fine with me.
And that’s how we broke up.
It was him or the dog.
I have no regrets about my decision.
Most Awkward Second Date.
A few months after choosing my dog over my boyfriend, some friends at work suggested that I go out with a new guy at work. He seemed okay. He was quiet. But, I was up for it.
We went on a date to dinner and it was okay. The conversation didn’t exactly flow and it was kinda awkward for some reason. But, I was willing to give it another shot. After all, who isn’t nervous on a first date?
So, when he asked me on a second date, I agreed and I assumed that we would be going out somewhere, but, instead, he suggested that we stay in and watch a movie (I know, I see right through this now, too).
That was fine with me and he asked me if I wanted to come to his house or him to mine. I suggested his house (so I can see what his digs looked like), but he told me that he actually lived with his grandparents. (This wasn’t a deal breaker because he was 19, and a lot of people that I knew still lived at home). But, I’m not sure why he gave me the option to choose, but then picked?
We made plans and he showed up at my apartment, movie in hand.
It’s funny now that I thought that the first date was awkward because this one was SUPER awkward. We literally sat on the couch, side by side and watched this stupid movie. Halfway through I was ready for it to be over because I’d decided that I’d rather be sleeping than watching a stupid alien movie with someone I had no chemistry with.
Apparently he had other things on his mind, because he started to try to flirt with me by tickling me.
This was weird.
At first, I kinda laughed it off. I didn’t want to be rude, but who, over the age of 12, actually likes being tickled?
Especially on a second date.
This went on, off and on throughout the rest of the movie.
FINALLY the movie ended and I, then, realized why you should never invite someone over to your house until you know them better because he didn’t leave.
I sat there and wondered what he was waiting for and why he wasn’t leaving.
How do you (politely) tell someone to leave?
“Like, not to be rude, but could you please vacate my apartment and never come back? K? Thanks!”
Now that I’m no longer a naive 19 year old girl, I’m fully aware that this “date” didn’t go in the direction that he’d planned, but I finally had to tell him that I was going to bed (read: LEAVE).
He quit his job the next week and we never spoke again.
This one isn’t actually funny at all, but a train wreck, nonetheless.
At 21, I’d finally given an old friend a chance. He’d been trying to get me to go out with him for years but I knew it was a bad idea. He wasn’t a good guy and he hung out in a bad crowd. But, he’d recently moved away, got a good job with his brother-in-laws business and seemed to be getting his life together.
I’d known him and his family for years so when he invited me to go out with his sister and brother-in-law to watch the night horse races, I was excited! But, I wasn’t able to get off work in time to go with them to the races, so I met up with them for dinner afterwards and we had rooms booked at the hotel next door.
We ate dinner and had a great night out and got back to the hotel room around midnight. We’d brought some alcohol with us but didn’t end up drinking anything, however, my new boyfriend was slightly irritated by this.
I remember thinking something was off with him when I told him I was going to bed, because he was obviously mad when he said, “It’s the weekend. I’m not going to bed, yet. I’m going to have fun.”
So, I went to bed wondering what his deal was. This guy had been chasing me for years and was always so nice to me. I didn’t think much of it until I woke up in the middle of the night to a strange scene.
My boyfriend was sitting at the desk in our room, on my laptop with headphones on, listening to rap music and rapping along. But, he was slurring his words and not making any sense.
He didn’t realize that I had woken up and was watching him as he picked up the (now empty) bottle of vodka and proceeded to take a drink- completely oblivious to the fact that it was empty or that he’d drank an entire fifth of vodka by himself in just a few hours.
Sensing that I wasn’t in a good situation, I chose not to stir the pot and went back to sleep without saying anything and planned on getting home ASAP the next day and breaking this off. Clearly, he hadn’t changed at all.
When he finally tumbled into bed at 7am, he was nearly laying on top of me, so I asked him to roll over.
Without missing a beat, he groaned and said, “Why are you such a bitch?”
He’d never talked to me like that before and I was shocked.
I assumed he was about to pass out, so I decided to go ahead and get up. I hopped in the shower and a few minutes later, he started banging on the door- furious that I had locked it.
He was yelling at me through the door, asking me why I had locked it and asking me why I was taking a shower. I tried to tell him everything was fine and I would be out in a few minutes but he started to freak out.
He started to pull on the door, trying to pull it open and I could hear the frame of the door cracking. I have no idea why he was so upset by my decision to take a shower. He was obviously belligerent.
I got out of the shower, but I was scared to open the door so I tried to call and text his sister, who was just a few floors above us in their own room, but they were still asleep and not answering.
I started to panic.
I sent a text to my best friend (his cousin); his parents. No one would answer and I didn’t know what to do.
He was yelling and trying to pull the door off. He was cussing and saying that I was going to break up with him now. I don’t know why he wanted in there so bad, and I contemplated calling 911.
After 10 minutes of this, I finally opened the door, and tried to gather up my stuff as quickly as possible. This made him panic even more and he was following me around the room trying to grab me and get me to stop. I finally got all of my things together without saying much to him, when he yanked my keys out of my hand, cutting my hand.
When he saw that he made my hand bleed, he threw himself down on the ground, with his back to the wall and started to punch himself in the head.
I was in shock.
I’d never seen anyone act like this before and I didn’t know what to do.
He finally threw my keys down and I snatched them up and bolted. But, as I waited for the elevator in the hallway, he ran out of the room with his bag and insisted that he was going with me (that was the original plan). I told him he could go home with his sister but he stood there waiting by me, quiet and calm as if he wasn’t just beating himself up in the room.
When the elevator opened, I got on and so did he. I told him that he was not going with me and I got off the elevator and so did he. We did this a few times before I finally got on and hit the number for his sisters floor instead of the ground floor.
I banged on her door and she was still half asleep when she opened and I told her what was going on. Her husband had to physically hold her brother back so that I could leave without him following me.
I left and over the next 2 days, he left me so many messages that my inbox stayed full. They ranged from apologetic to furious. It was insane.
I never called him back.
I never talked to him again.
I’m still not sure what that was all about.
Taking Slutty Pictures to a Whole ‘nother Level.
Is it normal to have this many bad dating stories??
When I was 20 years old, I started dating a guy that a friend had set me up with. Honestly, we had no chemistry but he seemed like a nice guy and he had his shit together. This was one of those relationships that I was trying to force even though my gut was telling me it was wrong.
Nonetheless, we had been casually dating for a few weeks when Halloween rolled around. He decided to have a party at his house and invited all of his friends. I knew some of his close friends but there were a ton of people there that I didn’t know.
He spent the night barely speaking to me and I felt weird being there and not knowing anyone. I tried to make small talk with some of the people there but I honestly felt like Gigi from the movie, “He’s just not that into you.” And I am not a Gigi kinda girl.
I tried to wait the night out to see if it got better, but instead everyone just got drunker and I had just gotten sober (so that I could drive myself home).
The final straw for me was when the group started taking pictures and one girl in particular was so wasted that she didn’t care that you could see her entire vaheen when my boyfriend threw her u over his shoulder and posed for pictures with her butt right next to his face, hanging her head down over his shoulder.
He was literally taking pictures with another girls vagina.
Right in front of me.
He didn’t understand why I was not thrilled with this scenario and had left that night without saying goodbye.
That was the end of that.
I’d Love to Take you Out, but…
Okay. So this isn’t actually a date but it almost was.
An old friend connected with me after not seeing each other for a couple of years. He had a great job but that job required him to travel a ton and when we reconnected, he wasn’t working there anymore.
After a week or so of talking, he asked me out and I agreed. But then there was a but.
As it turns out, he didn’t have a job anymore because he’d gotten into some trouble with drinking and lost his drivers license, along with his job. So, although he wanted to take me out, he couldn’t actually pick me up, and asked if I would be okay with picking him up.
Due to this new information, I decided not to go on that date.
At least I was getting smarter at this point.
You know how you can trick a dog by waving something in their face? This happened to me once in the form of cheap flowers.
At 22, I had been dating a guy for a month or so and we’d just gotten back to my house when he told me that he had to help a friend out early in the morning so he was just going to stay at his house that night so he didn’t have to drive so early the next morning.
He spewed this BS story (that I saw right through), and handed me a cheap bouquet of flowers wrapped in plastic, and left.
I thought to myself, “is he serious right now?”
The next day when he came over, the hotel key card fell out of his pocket right in front of me.
Do you have a bad date story?!! Share it below!! Tell me I’m not alone! 🤣🤣