Real stories of real dates with real guys


Read this if you're in a committed relationship and assume that everyone else wants to be

NOTE: This is picture #9 that comes up when you Google Image "dating apps". This is not mine, I did not make it, I'm not trying to steal it. It's just cute.

There has never been a shortage of people and now there is no shortage of ways to meet and mingle. In this city the world is your oyster and there are so many fish in the sea. But if I’m going to use ocean metaphors to describe dating then you have to admit there is a lot of plastic in the ocean. To really put things in perspective, by 2050 there will be more plastic in the ocean than fish and that is a truly terrifying thought.

For every right swipe and “not bad date” there are endless left swipes that happen within a fraction of a second and cringe-worthy dates that amount to nothing more than a good story. The “at least I’ll get a good story” defensive is how people set expectations so even an absolute disaster has a silver lining. How bad is bad? You decide.

Real stories of real dates with real guys

To be clear all of these guys seemed nice, legit, smart, and interesting via text and in profile. In other words there were no shirtless profile photos, no mirror pictures, no gym selfies and none of them used a cheesy pickup line.

Guy who couldn’t make decisions: The first 10 minutes of the date were a microcosm of what a relationship with this guy would be like. He couldn’t make a decision about anything and even when I suggested something he’d say “Is that what you want”? It took almost 30 minutes for us to be seated and have an actual conversation because we went through the question game for everything from where to go and where to sit once we got there.

Guy with confusing definition of masculinity: I went on a date with a guy one time who insisted on ordering a Manhattan even though we were clearly at a place that was not equipped to serve them (read: they had plastic cups). He ordered his Manhattan and after one sip decided he needed a Diet Coke to chase his drink. If you don’t believe my assessment of the situation just Google “manly drinks”.

Guy with no tact: One time I went out with a guy who was disappointed from the minute I got there. He did a very obvious once over followed by a very obvious look of dismay. He spent the rest of the night dropping subtle hints about how he was unimpressed by my fashion sense. At one point he suggested we go somewhere else but then quickly retracted his statement because I “wouldn’t be able to get in wearing that”.

Guy who kept talking about how much money he makes: Bonus points for never actually saying how much money he was making though. Oh and in case you’re wondering we split the bill.

Guy who suggested Taco Bell: This one is self-explanatory and was a legitimate suggestion because after our first date (not at Taco Bell) he requested the second to actually be at Taco Bell. This did not happen.

Guy who was still using pictures from 5 years ago: I was so shocked after this date that I broke my no Internet stalking rule and found him on Facebook. The pictures from his profile were all dated 2013 and earlier. I don’t care who you are; no one in their 20s and 30s looks like they did 5 years ago. No one.

Guy who was disappointed that I read: He noticed a book in my bag at one point and aggressively rolled his eyes. When I asked what that was about he said “You’re one of those girls… girl who carries a book with you” No sir, I’m one of those girls who reads said book.

Guy who thought NYC > everything: I didn’t actually go out with this guy because he basically started a fight with me about how NYC was the greatest city to live in. When I asked him where else he’d lived he responded “I don’t need to live anywhere else. I just know”. Needless to say “open-minded” was not listed on his profile.

So…. dating sucks?

There is another side to the coin though and it’s not talked about often enough. Writing about dating is like writing about the news. The good stuff is promising and uplifting but it’s not entertaining. You hear the statistical anomalies of couples getting married who met on Bumble and they are considered a success story and the only ray of hope in modern dating. Somehow the narrative of online dating has been distilled down to a single shade of horrible which makes us overlook the great stuff that falls somewhere between a bad date and a wedding.

I could make a similar list about the good experiences I’ve had filled with things I’ve done, places I’ve been, and people I’ve met while dating. But those won’t be nearly as entertaining as the story of the date that I went on two days after the 2016 election.

A friend texted me the other day asking about my dating life. I said I wasn’t really dating right now because I wasn’t interested and her response was “I wish I knew how to help”.

Being single and dating or not dating is not a circumstance that needs to be “helped”. It’s definitely weird to date in a world where it takes fewer clicks to find a potential date than it does to order delivery to my door. But it’s weirder when people feel bad for me that I have the opportunity to meet new people.

Last I checked our generation was obsessed with novelty and craved new experiences but when it comes to dating we forget that it's another opportunity for just that. The people peddling this narrative of dating misery are likely either completely out of touch or are doing something wrong.

So what’s dating in New York City really like? It’s what you’d expect if you walked into a party with a bunch of strangers: You’ll make small talk with a lot of people, keep your distance from others, and maybe spend the whole evening chatting with a few people. But just because you didn't walk out with a new best friend doesn't mean that it was a waste of time.