I used to be that overly optimistic person about dating. I would proclaim, “I love first dates”. This was because, for most of my dating experience, I had really good luck with them. New restaurants would be explored, drinks would be had, and question games would be played. If you are not scared of a few awkward moments, what is there not to like?
I must have hit an invisible off switch because at some point my first dates started getting strange. I slowly but surely found myself hoping they would end sooner, so I could get home and my roommates about my awful night. I even swore off dating forever after a date with a guy so drunk, he threw up at the table — more details on that to come.
I do think it is important to note that I met all these guys online. So I went into these first dates pretty blind beyond a profile, a few pictures, and a day or so of service level conversations.
In hindsight, there are a few things I would have done differently but that is not what this story is about. Here are the three worst first dates I ever had, and no, I am not making these up.
Date 1 — Mama’s Boy
Suitor: Tall dark handsome, 27 (age), Hairdresser. We will call him Jason.
Jason was so sweet over text. In hindsight, after having all the sweetest in front of me in person, too sweet. We met at a hip restaurant/bar on a Sunday night at around 7pm. Naturally, I was expecting to eat dinner.
The first thing Jason told me when we sat down is he had already had dinner with his mom. My first thought was, how cute! Until he continued to talk about his mom for the next hour.
He not only lived with his mom but she was his absolute whole world. I saw pictures of them, heard stories, and even added he could not wait for me to meet her. We just had a beer, but I could have drunk five in that hour.
As we were finishing our drink, Jason asked me if he could feel my hair. I thought it was odd but I let him go ahead and have a touch. He was giddy over how soft it was.
He then asked if he could braid it while standing up out of his chair to position himself behind me. I could have spit out that last sip, but instead I said, “maybe not here… maybe later”. Nicely trying to divert the situation.
As you guys should be able to tell from this point in the story, Jason was simply too sweet for me. I had to let him down easy when I received a playlist the next day. A playlist of love songs he had made, I quote, “about our future”.
Date 2 — The Party Animal
Suitor: Surfer, 30 (age), Computer Engineer. We will call him Brian.
Brian and I immediately started off on the wrong foot. We were having trouble locating each other outside of the restaurant in a heavily congested area, so we got on a phone call to figure it out.
Once figuring out we were both in the same place, he stated, “I am standing on a table, in a white shirt, doing a Shaka sign”. I should have walked away right there. How was I going to take this guy serious?
Once we finally got inside together Brian proceeding to tell me about his heavy partying lifestyle. He shared he went out 4–5 nights a week. I joked about being a grandma and asked how he holds down a full-time job with that schedule.
He shared, “you just do drugs during the day, and drinks at night”. He stated it as casually as he stated where he was from. He then told me he was a practicing Mormon. I think he misread the confusion on my face as a curiosity.
If things weren’t cringy enough, he then asked if he could finish the food on my plate. I was not good at saying no in these days, so I mustered out a sure, even though I was planning on saving it. He didn’t even move my plate. Just reached over and forked what he wanted, bite by bite.
To wrap things up, he asked for me to join him for drinks at a raging bar a few shops down. I told him I worked the next day and although true, I would have found any excuse to not go.
He then asked me if I would just “walk him there”. As if this party animal needed a chaperon. I knew it was just an excuse to see if he could change my mind along the way. But along we went.
Me, walking my Mormon date to a bar, dropping him off for a Tuesday night out. We never spoke again.
Date 3 — Projectile Vomit
Suitor: Fraternity Bro, 35 (age), Real Estate Agent. We will call him Chad.
I met Chad on a hot Orange County day in August. We met at a fancy new restaurant in Newport. They only did valet. After dropping off my car I found Chad at a table near the bar. He was already through a drink but I was not late.
I sat down and perused the drink menu. He ordered a second for himself and one for me. Right as the waiter stepped away, and Chad and I settled in for our first round of questions, a man approached the table.
It was a fraternity brother from college and they just had to take a shot together. I repeat, on a first date, before we knew a single thing about each other we paused for him to take a shot. He did at least offer me to join, but I politely declined and while ignoring my inkling to get the heck out of there.
As soon as he returned to the table I noticed the slur in his words. Slurs turned to wobbles, and before I even could catch on to what was happening, it hit. He swung his body to the right, pushed open a side door, and threw up all over the outside patio. Yes with tables and people.
He immediately apologized to me and A-lined it to the bathroom. I sat in shock and horror as the whole restaurant turned toward me. I took a large last sip of my drink, grabbed my purse, and headed straight to exit. Beet red I’m sure.
When I showed up the valet, the nice man stated, “already?”. My car was in valet for a total of 23 minutes. The longest 23 minutes of my life. I think he could tell I had had a rough night as he insisted the valet was covered. I should have asked if he was single.
Brad was immediately blocked. I do not think either of us could face a conversation after that experience.
. . .
So there you have it. The three worst dates I ever had that have become my best dating stories.
Jokingly, I remind my boyfriend to never make me single. I don’t want to be in the place to go on first dates again.
But if I had to, could it get any worse?
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This post was previously published on Hello, Love and is republished here with permission from the author.
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