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Writer's pictureAshley Garrett

Three of the Worst Dates I've Ever Been On

This empty post has been sitting in my drafts for months. The only thing saved was the title, but that's all I need as a reminder for what to write. There's no way I could ever forget the 3 dates I want to tell y'all about. I've been a consistent dating app user for over 6 years and I've even been banned from Tinder, but that's a story for another post. I've had my share of awkward dates or meeting up with someone who very obviously lied about their height. That's mild stuff that is likely a shared experience between everyone, but this post is for the uniquely awful experiences. Let's get started with the worst of the worst.




First worst date: I matched with a young man, who happened to be Brazilian. I don't remember what his profile said to sucker me in, but it must have been good. I don't typically match with anyone on the apps that makes it clear that they are here temporarily. I'm not even calling out international people, but anyone. I would never match with a Disney intern either. Oh. My. Gosh. I guess I'm old fashioned, but I date to build something lasting and that's hard if it's gonna turn long distance. Anyway. I don't remember how long we messaged back and forth, but we ended up agreeing to meet at my local Starbucks. When we order, he offers to pay for my tall drink, but his card is declined. Big yikes. Like secondhand embarrassment for him. I will pay, but he found another card and paid. This was a tiny hiccup that could happen to anyone. It got really uncomfortable when we went out to the patio to sit. We were there for an extended amount of time, maybe 2-3 hours. The conversation was okay, although he was talking a lot more than I was. I hate a one sided conversation. Somehow, he arrives at the notion that it's appropriate to start kissing my neck on this patio, surrounded by people and kept going! Not a quick thing. After I snapped out of the "what is happening" I pushed my chair back to create distance.


Since this Starbucks was near downtown, there's a lot of homeless people around. One walked up to the patio and started vomiting before passing out. Obviously, this wasn't my date's fault, but environmentally it was bad and his reaction kinda sucked. When the man fainted and hit the ground, the first thing my date said was "Wow, that's disgusting, let's leave." I am not one to play into the bystander effect and I was absolutely about to call someone for help, but luckily a nurse ran out of the store and helped the man. Blatantly ignoring someone in danger and calling them disgusting really doesn't sit right with me.


Somehow, the date continued to get worse. When we got to our cars, he tells me to come home with him. Yes, tells. Does not ask. I say "no thank you, I have dogs at home and I've been out for a few hours now." Then, he literally starts to taunt me. He calls me a name, which I don't remember now but he literally changed my name to essentially call me boring. He says he doesn't understand Americans because they just want to go out on dates and talk to get to know each other when they could be at home doing PHYSICAL stuff. The nerve. This man really thought he could buy sex with me from a $5 coffee. The next day he texted me with the taunting name he had been calling me and I blocked his number. This is one of the only times I have ever ghosted someone. I acknowledge that there are cultural differences between us, but that doesn't change how he made me feel, his lack of compassion for a stranger, and the fact that he literally thought a cheap, declined, coffee purchase could buy him sex. Get outta here.


The second worst date comes down to politics. It was also the only time I've left mid-date. As we were dining at Homecomin', somehow our upbringings and what our families are like surfaced. I said I'm nothing like my family. They're Trump people and I'm the opposite. This boy was shooketh. He said "So you're not...conservative...? I said "No, are you?" He of course said yes, but we changed the subject and I had no intentions of getting upset and leaving. I mean there probably wouldn't be a second date since I view the current political climate as a judge of a person's character, but I was fine to finish it out. We left the restaurant and strolled through Disney Springs for a couple minutes, but he had to bring it up again.


He said "So, you really don't like Trump?" And I said "I really don't. Actually, I hate him. You tell me why you like him." So of course the first thing he said was economics and a strong economy. I asked him to explain how he, himself, personally would benefit from a strong economy. He couldn't really. (Spoiler alert: I personally believe the economy has nothing to do with anything unless you're a business owner and even then is tied into capitalism and capitalism is toxic). I said "Okay, because human rights issues and his misogynistic attitude affects me personally, and his hateful, racist rhetoric towards immigrants who are keeping this country running, legal or not, and his hate towards gay people and no hesitation to make fun of disabled people affects people I know personally." This date happened in 2017 so you can imagine I had no idea of the true Trump horror we would all experience. This boy actually then told me that I created the idea of misogyny in my head because women would never be valued in politics and shouldn't actually even be voting. I had conveniently steered our stroll towards the garage where I was parked and I said "There is no way you just disrespected me, a woman, by saying we're not equal. Goodbye." And I walked to my car. :)


The third worst date actually was awkward and bad, but kinda ties with several awkward dates I've had in my time. I just picked this one because of the audacity of the future follow up. I matched with this British guy (who had lived here 15 years so I knew he wasn't going anywhere) and I decided to meet up with him. He was not at all physically attractive, but I actually rarely match with people based solely off looks. In his case I was curious about the accent, sense of humor, and our conversation had been good. He kept saying he wanted to take me somewhere nice for our date and he (yes, HIS IDEA) wanted to go to Ruth's Chris. I know Ruth's Chris is fancy and more like an anniversary place rather than a first date. But when we were seated, I totally thought this would be a normal date.


We ordered drinks and I was totally scoping out the menu. The server came back and asked if we were ready to order food. My date looks at me and goes "I'm not hungry. Let's do drinks only." Obviously, I figured out it was about money, but I wish he had been transparent and said "Let's meet here for drinks." Or even once we sat down say "Are you okay with just drinks tonight?" But it was just so weird happening in front of the server and it clearly being a lie. From that moment on, I got that despite him likely wanting to pay, money was an issue for him so I didn't even want to order a second round. But I felt so bad because we were taking up prime real estate for our server in Ruth's Chris. They kept checking on us too as in yes, please order something else or leave. This man was a car salesman and kept talking about how sales were down, so I definitely got the hint. It was a very one sided conversation, but when he asked me out again, I said yes. I figured maybe he's nervous on this first date.


The second date, we went to a sushi place (his pick and it was so bad) and then drinks at Ale House and that was awful too. But when we left Ale House, I went in to kiss him because no attempts had been made on his part and I gotta know if there's something there. It was so awkward and he so obviously didn't want to for whatever reason. It felt like kissing a grandpa or something. So I left and texted him the next day saying I don't think we were the right fit. Fast forward to a year and a half later when I'm searching for cars to buy and I asked about a car at his dealership. I submitted a general online inquiry. Anyone could have gotten back to me. Instead, he texted me from his phone, said "Hey, I'm so glad I still have your number and you want to see this car. When can you come in?" I SAID HELLLLLL NAW and that's when I started looking at another model car completely. But I was just like wow. The audacity to try to sell someone a car and collect commission after awkward dates. No hunny. Should've let that roll by.


I've been through awkward, uncomfortable, inappropriate dates, but I'm so thankful nothing legitimately traumatizing or horrible has happened to me on a date. As females, we hear date rape stories and assault all the time. More rarely, but sometimes, ending in murder. I can look back on these dates now and laugh. For that, I'm thankful.


xx Ashley

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