The Top 7 Worst Dates I’ve Ever Been On

I would like to start out by saying that this post is not meant to deter you if you’re a woman out on the dating scene whose interested in online dating. I have been on a lot of dates and the fact that only seven of them come to mind as truly terrible makes for pretty good odds. 

Often times I find that dates are usually just…okay. Not bad, but maybe just not that great. And occasionally they’re really wonderful. So don’t let me scare you and prevent you from putting yourself out there because typically the worst case scenario is that you have a mediocre date and you go home and order a pizza afterward. No big deal. 

However, if you do have a bad date let these seven awful stories give you a sense of comfort because you are definitely not alone. 

Sometimes they’re bad because you don’t have any chemistry, sometimes you just flat out think they’re an asshole and sometimes they’re just plain creepy dudes. Whatever the case may be, hopefully, the exit strategies I’m sharing below can help you if you ever have the misfortune of finding yourself in the middle of a terrible date. 

#7: THE AWKWARD ESCAPE ARTIST

I went on a date with a guy (let’s called him Jeff) who was new to the city, doing the techie transplant thing and who lived out by the beach in the Outer Richmond. We met up on a late, sunny afternoon at a coffee shop in his neighborhood. When I arrived he came bumbling out of the restroom and told me he decided he didn’t want coffee after all and that we should walk down to the beach. 

The entire walk there he asked me zero questions about myself but told me several stories about pranking his college roommate and how he sometimes doesn’t leave his apartment for a week straight. Fantastic. 

Once we were at the beach we sat down in the sand and without saying a word, he reached over and removed my sunglasses and put them on. I had known him for 10 minutes (literally). He then insisted that I take my jacket off so I’d be more comfortable and if you’re from San Francisco and have been to the cold af beach you understand how absurd that is. 

After all of 5 minutes, he decided he didn’t actually want to hang out at the beach and that we should walk back. He asked me for restaurant recs and I told him there was a great Chinese restaurant (RIP Shanghai Dumpling King) in his neighborhood. He suggested we go to it so we started walking in that direction. 

Then he suggested we take it to go and go back to his apartment, to which I replied with a hard no (you can’t just take soup dumplings to go, wtf) which prompted him to oddly start babbling about how he “forgot” he needed to move his roommate’s car. 

He then stopped walking abruptly and pointed to a random car across the street and said “that’s his car. If I don’t move it he’s going to kill me. But we should get food another time for sure”. Then he scampered off across the street towards the car without another word, looked around and then ran off in the opposite direction and disappeared down an alleyway. Goodbye Jeff. 

#6: THE GUY WHO WAS ADOPTED 

You want to know how I knew this guy was adopted? Because he told me. Over and over and over. Not only did he tell me all about how he was adopted but he also told me about how his biological parents were involved in a murder case. 

He then went on to detail every crime anyone in his adopted and biological family had committed, many of which included rape, incest, and murder. 

Fabulous. 

When I was ordering a Lyft at the end of the date he kept looking over my shoulder and asking me where I lived. Then he awkwardly kissed me on the forehead (I’m sorry, what?) and I jumped into my waiting Lyft and started googling his name to see if he had recently escaped from prison for making skin suits out of his tinder dates. 

#5: THE GUY WITH AN AGE FIXATION

I was probably around 21 when I met up with this guy who was 29. In my opinion, not much of an age difference but I’ve always dated older guys. He, however, found our age difference to be extremely fascinating and it dominated the conversation. 

We were going to see a movie which is a terrible first date idea but I was trying to be easy going. On our way up to the movies, we saw a group of high school kids clearly on their way to prom since they were all decked out in frilly dresses and tuxes. My date could not stop staring at them and then whispered: “you look like you could be one of them”. Um, thank you? 

I can’t really remember many details of the movie we saw since I was desperately waiting for it to end but I do remember it had a young teenage girl in it with blonde hair, which prompted him to lean over 3 times and whisper “you look just like her” to me throughout the film. I was beginning to realize he may have been hoping I was secretly 15 and I got the eff out of there. 

Oh, and at one point he also spent 15 minutes telling me how he was currently in a feud with his roommate because he “didn’t want to be an animal” with him. Exsqueeze me??? What does that even mean sir??

#4: THE PADDLE BOAT INCIDENT

Alright, so this one is partially my fault. 

I had pregamed a little too hard for our first date and therefore was pretty fuzzy on the details when it came to you know, what he looked like and his personality. I do remember having a nice time and probably one too many whiskey sours. 

Flash forward to our second date a few days later and I am horrified to see that the guy I was picking up was not, in fact, as cute or as charming as the picture my drunk brain had painted. 

Listen, I’m not trying to be an asshole but I’m just not attracted to guys who can’t dress themselves. Call me shallow but I’m just not into it. No thanks. 

He was wearing pants that were about 3 times too big for him, a bizarre baggy windbreaker and the most heinous glasses I’ve ever seen in my fucking life. His hair was slicked back and greasy with gel and I realized that I had made a very big mistake. 

Now before you start thinking I’m a total bitch let me be clear that I was also not impressed with his conversation skills. He told me back to back rave stories, a long drawn out tale about an “epic” camping trip and how he considered himself a sommelier because he use to work at Whole Foods (what?). 

We went to Golden Gate Park which was not an ideal date setting for me at the time because I was currently dealing with a bad arthritis flare up in my foot and wasn’t really up to taking a long walk. He ignored this fact when I told him and suggested we walk around the entire park and became irritated when I need to sit on a bench for a break. Charming. 

He then suggested we rent a paddle boat and go out on Stow Lake. I really did not like the idea of being stranded at sea with him but he insisted. He told me he thought I should paddle the entire time so his legs could get a break and he kept trying to kiss me, only succeeding once THANK GOD. 

At this point I was so unattracted to him I considered diving into the smelly gooey lake just so I could escape him but before I could he pulled out his phone and said “let’s take a picture!”. 

Ugh. I did not want to be associated with him or his hideous glasses in any way so I was not excited, as is made evident by the photo we took below. Look at my face. That is not the face of a happy woman. 

After our date, I drove him home and he asked me to come inside, an offer I firmly declined. I texted him as soon as I got home to let him know (as nicely as possible) there would not be another date.

#3: THE LONGEST DATE IN HISTORY

This date lasted a whopping 6 hours and was terrible from beginning to end. Alas, I was 18 and had no idea how to get out of terrible dates and so instead endured it until the last minute. In order to spare you the long, unfortunate details I will just list some highlights that I believe do speak for themselves.

-We started at a sandwich shop where he told me he forgot his wallet and asked if I could spot him. 

-I was ready to leave after this but then he suggested we go to the movies so we hopped on the Muni to head downtown. He purchased a child’s ticket (he now all of a sudden had found his wallet) even though he was most certainly not a child. 

-A BART cop stopped us at the Powell St. Station and asked to see our train passes and then issued him a $100 ticket for using a child’s pass. He screamed at her and then spent 20 minutes calling both his mother and his father asking them to pay for the ticket for him. Yikes. 

-He all of a sudden had a sweet tooth and dragged me into an ice cream shop where he purchased a giant sundae that was clearly not meant for one person and then yelled at the cashier because he thought $7 was an outrageous price and after they had already made the gargantuan sundae decided he didn’t want it anymore. 

-When we got to the theater there were two movies that were starting soon and he asked me which one I would like to see. After I told him my choice he said:  “Okay cool, we’ll see the other one”. 

-When we were paying for the tickets the cashier asked if we were paying together and he cackled and said: “I’m not paying for her!”.

-He talked throughout the entire movie and had the worst breath of all time.

-When we were leaving he told me how he was thinking about auditioning for The Voice and then began performing a Bruno Mars song, loudly and VERY badly, in the street. I walked ten feet ahead of him. 

-He asked me if I could look up the bus times on my phone and then asked me to wait with him. I finally stopped being a pushover and said “that’s going to be a no for me” and raced down the steps to the BART station and got the hell out of there. 

#2: THE SHORTEST DATE IN HISTORY

This date lasted an entire 40 minutes and honestly, that was 40 minutes too long.

I met up with this guy who had my ex-boyfriend’s name, which honestly should have been a red flag from the start. He was new to the city, having just moved here for work from New Jersey (another red flag. Kidding! Kind off…). He also had this absurd Johnny Bravo-ish hair that I could not stop staring at. How did he get it so high up? How long did that take him? 

He was immediately very cold and unfriendly. I asked him about his job and New Jersey and how he was liking the city. He went on and on about the company he was working for, told me some very dull stories about his hometown and said that he hadn’t really gone outside of the 4 block radius of his apartment since he got to San Francisco. Basically, he was a real thrill. 

When we got to the bar he “shhhed” me when I asked him what kind of food he liked and said “can you wait until we sit down away from everyone?” as if I had actually asked him how much money he made and if I could have some. 

He clearly was not into me, which was made evident by the way he didn’t ask me a single question about myself and often times stared off out the window with a dead look in his eyes. I tried making conversation but he basically answered everything with a yes or a no. Awesome. So fun. 

I guzzled my drink so I could leave and he said he would close out, so clearly he was ready to go as well. When he came back he pointed to my top (an amber colored sweater) and said “oh hey, your shirt matches your drink glass” (I had ordered a Moscow Mule) and I said “Yeah, I planned it that way” jokingly and he just stared at me with his mouth agape looking horrified for a reason that was not clear. “I was joking…” I told him. OBVIOUSLY. Did he think I spent hours coordinating my outfits to the future vessels that would contain my next alcoholic beverage? Did he think I could see the future? Honestly, that would have been very useful as I could have skipped this date entirely. 

Then I started to go outside and I told him my lyft was almost here which apparently surprised him because he said: “you already called one?” YES. OF COURSE. 

Finally, once we were outside I began putting my jacket on and I looked back at him and saw him doing that bizarre staring thing again, this time just looking off blankly into the street. I asked “Are you good?” and he glared at me and snapped “Yes,  I was waiting for you to put on your jacket, god”. Okaaaaaay. 

I saw my lyft was approaching so I said goodbye and started walking towards the street corner, which happened to be in the same direction he was walking in and he laughed and said “Um…you don’t need to walk me home” LOLOLOL. Okay. Right. 

Then I laughed (too hard) and got into the lyft waiting for me at the corner and turned back and said: “I would never”. 

#1: THE CREEPY DENTIST

I’ve saved the grossest for last. You’re welcome. 

I met this guy at a brewery downtown and he was nice enough. At first. He told me about how he was in dentistry school and how he was new to the city. He was friendly and made good conversation so, so far so good. This was the first fifteen minutes. 

Once we got our beers we sat down and continued chatting. He had asked me about my name and I was telling him how it’s my grandma’s name when he all of a sudden completely interrupts me and says “I really want to kiss you right now”. I was so taken aback because while this could have been a romantic line if I had say, known him for more than a handful of minutes, it was the most absurd timing. A few minutes into our first date, while I’m talking about my grandmother. Ew. It was all downhill from there. 

I made a joke about how I had literally just met him moments before and that he should cool his jets and he said “I just can’t stop staring at your mouth”. Ew. Ew ew ew. Nope. No thanks. 

After our beers he suggested we move onto another bar and I really didn’t want to but at that point, I had only been there for 30 minutes and I felt like I shouldn’t be a total asshole and bounce. 

So we walked a few blocks to Local Edition, a speakeasy-style bar downtown, and we get another beer. The entire walk there he was trying to hold my hand and put his arm around me. I told him that I was not down with that and he said: “I guess you’re just not a very affectionate person”. Um, I do not know you, sir. 

Once we got to the bar we grabbed another round of beers and he continued to be creepy af. He kept trying to massage my neck and kiss my cheek. I told him repeatedly that I did not know him like that and that I didn’t want him to touch me. He laughed it off as if I was being flirtatious. No, bitch. I think you’re gross. Go home. 

Finally, I couldn’t take it anymore and I told him I was taking off. He seemed so genuinely puzzled by why I would leave so soon and STILL tried to kiss me goodbye, a move that I dodged with such agility that my lyft driver who saw the entire exchanged applauded when I got into the car. 

So the date was gross but it gets worse you guys. 

The next day he texted me saying he had the best time (what?!) and that we should grab coffee soon. I typically try not to ghost dudes because I obviously don’t love it when it happens to me, so I usually will just text someone and let them know if I don’t see us going on a second date. But this guy was foul and deserved a proper ghosting so I ignored his text and all of the other ones he sent me that week. 

Until that is, he sent me a novel about how much of a bitch I was and how I had just used him to get free drinks. He’s referring to my two extravagant beers by the way. He then started blowing up my phone with links to events in the city that had free drinks and food. How sweet!

…that last sentence was meant to be sarcastic but also, it was kind of useful info. Just saying! 

So I replied and told him his behavior had been wildly inappropriate and that I had no idea he was so strapped for cash and that I could venmo him the $10 for my beers asap. Then I blew up his phone with 20+ links to debt relief websites. And that, thankfully, was the last time I heard from the creepy dentist. 

I hope my bad date stories have given you a laugh and a little comfort in knowing that girl, you are not alone. Tell me your dating horror stories in the comments below!

Xo, She