12 People On Why Dating Is A Nightmare In Their City

12 People On Why Dating Is A Nightmare In Their City Hero Image

Everyone thinks their city is the worst city to meet people.

"All the guys are such douchebags here."

"Literally no one is single."

"I see my ex everywhere I go."

The reality is, of course, that each city has its pros and cons. For example, here in New York City, it's far too cold to go out and socialize sometimes, but that same brutal weather has caused the "cuffing" phenomenon, in which people who would normally rather be single find themselves wishing to be attached to someone with whom they can spend prolonged indoor time.

But there are those dates (or non-dates) that are so quintessentially your city — like getting trapped with someone unsavory on the subway — that other locals can relate to so well. The usual response: "That would happen here."

So, we gathered those stories from our friends around the country, and these are our favorites:

San Francisco: "Which tech company do you work for?"


I haven't been really dating long term in SF, but almost every encounter begins with, "Which tech company do you work for?" or a discussion on the person's "next big idea." I work Sales for a large, tech company that has been around for 30+ years now: Oracle. And, on almost every date I've had, the person has remarked, "Oracle?! Why do you work for them? You're too cool for Oracle." People have this misconception that the only eligible bachelors or bachelorettes either work for trendy new startups or storied tech giants, like Google, Apple, or Facebook. So, you come into Silicon Valley working at a tech company like IBM, Oracle, or Microsoft (the "grandpas of tech") like I did, you're not as eligible.

— 23, Business Development Representative


Detroit: "Everyone knows each other from high school or college."

One of my guy friends invited me out with him one night, and I met one of his friends for the first time and we really hit it off. Turns out he dated a girl that I knew from the University of Michigan (where I went to college), but I never had met him before. We started going on a bunch of dates over the course of a few months.

On one of our dates, I’m standing at the bar chatting with his roommate when suddenly, I looked at the entrance and his ex (the one I knew from college) walks in. She had been living in Philly and moved back to Detroit the day before. It's just my luck that we would run into her on her first weekend back. But it just goes to show how small a city it is. Everyone who goes out goes to the same bars. Everyone knows each other from high school or college. Everyone dates each other.

She proceeds to ignore my friendly attempt at hello, and spends the rest of the night glaring at me and blatantly talking about the situation. About a week later, things ended between the guy and me, and now they are back together.

— 23, Sports Reporter/Producer


Los Angeles: "The conversation was like pulling teeth."

It has been my experience, largely, that if you work in entertainment (which a lot of people do), you are seldom around straight men that aren't super full of themselves. Not that they don't exist, they're just hard to find. So, with that said, I've had to rely largely on dating apps.

So, I met this 30-something year old guy who lived in Beverly Hills on a dating app. I live in Santa Monica, so it was already pushing the boundaries of how far I'm willing to travel for a date (traffic is REAL in LA). He asked me out pretty immediately, and I respected the fact that he took initiative and skipped the week — or two — of small talk and texting, so I said yes. It alarmed me, though, that he kept trying to get me to decide the location despite the fact that it was his neighborhood.

After much back and forth, we chose to meet at a coffee shop near him. He looked a lot older than his photo suggested. After we got our coffee and went to sit down, he awkwardly sat next to me on the far side of the table rather than across. The conversation was like pulling teeth; all I learned about him was that he had never lived outside of the neighborhood where he grew up, and he couldn't actually tell me what he did for a living ("A little of this, a little of that ..."). The fact that I even got that information out of him was a miracle. It was such a struggle to keep the conversation going that when he mentioned he had Torah class following our coffee date, I leapt at the opportunity to bolt. Total date run time: 25 agonizing minutes. Nothing tragic happened but it was painful all the same.

— 27, Casting Coordinator

New York: "He turned out to be a secret sex fiend."

I matched with a guy on Hinge who seemed really lovely. He reached out to me initially on the app, and actually wanted to engage with me about the fact that I was a writer. He didn’t wait to respond or play dumb games, and would always write back with enthusiasm. Another good thing off the bat was that he wanted to make a concrete plan, and to do so relatively quickly after exchanging texts. (I hate when dudes just want to text or they assume asking “Drisnkstonight?” the night of counts as asking someone out properly.)

Anyway, we got drinks at a cute cocktail bar and then roamed around Williamsburg as it started to snow — very romantic. We went to the BK Night Bazaar and got beers and watched some terrible painter make some dumb installation and laughed. At that point I knew he was a programmer and worked for some social media marketing company (it seemed like it was definitely an “income source” but not a passion project). Since he seemed artistic and like a “go-getter,” as my mom would say, I was curious to know if he did in fact have a passion project. So later on in the date I asked ... and he certainly did. He clearly had been avoiding it, because he responded that he had “kind of a side start-up, that isn’t really a start up yet.” Vague. I pressed further. It turned out he was making a porn aggregator to make porn-surfing easier from a UX perspective. I believe he called it “Kind of like Pandora for porn — it gets to know your preferences.”

It just goes to show that even if someone is emotionally attentive and has a college degree from a great college; he or she can turn out to be a secret sex fiend of some variety. I now call him “PORN MAN” in my catalogue of terrible dates.

— 24, Freelance Writer


Memphis: "These jeans cost me $300!"

The amount of douchebags I've experienced in Memphis is staggering. You can spot them in their bedazzled shirts and designer jeans. I was dating this guy who was really into himself. He was an aging 30-something dating me, a 24-year-old at the time. Those types of guys are so easy to spot; older guys trying to be younger with their gelled hair, tight shirts, designer jeans and cowboy boots. Anyway, he meets me and my cousins at the bar. I was a few drinks in when he walks in wearing the most hideous jeans I've ever seen. The stitching was neon orange they were horizontally shredded all the way up the fronts of them.

My cousin immediately dies laughing while my boyfriend starts defending himself saying, "What?! These are designer jeans! They cost me $300!" Needless to say, that relationship soon ended. Above anything, he was entertaining. But he could only think about which outfit he was going to wear the next day.

— 27, Esthetics Student


Chicago: "I don't like New Yorkers."

We had a work outing to the Cubs game, which was a blast. My friends and I were flirting with this group of guys sitting in front of us, and after a few beers, I gave my number to one of them. I honestly didn't expect him to contact me, but the next day he did.

We became pen pals for a few weeks. Neither of us knew what the other looked like, so while we were texting we awkwardly exchanged last names. (Let the stalking begin!) Finally, we make a plan and he picks a great bar. I get myself hyped up for a date and he cancels five minutes before I was leaving. We set another date for the following week and finally meet up. He texts me, "I'm in the red sweater..."

Anyway, he was a really nice guy and we were on this rooftop for three hours. (I don't really know how to ever end dates.) Although he was nice, there were little things that I noticed throughout the date. He was so Midwest, which one would expect when living in Chicago, but he seemed like the kind of guy that has never and will never leave Chicago. Being an East Coast girl, I love Midwest guys (they just seem manlier), but don't love it if they are close-minded. He claimed not to like New Yorkers (all of my family and friends are in New York and I could very well live there too) and he thought I was faking my love for country music.

The date ended, and we hugged goodbye. He continued pen-paling me but we never met up again. I'm not unhappy about it. The guy just loves to text — mostly strong opinions.

— 27, Account Manager

New Orleans: "I'm already too in love with the city."

I dream of the day when I meet a girl at the Fly watching the sun set over the Mississippi. Her dog comes over to play with me and, under the influence of a Sex Wax Daiquiri, I ask for her number.

But that hasn't happened, of course. I'm not sure where I met this one particular girl — maybe a start-up incubator, a Teach for America event, Tinder, Hinge, one of those — I just know it wasn't very glamorous. She had told me she'd never seen Rebirth, so the first date was an obvious choice.

We're inside. Cover paid. Two High Life’s at the bar. The band kicks up. The tuba rumbles across the floor, up into your chest. She’s enamored (with me or the night, I'm not sure). As I'm standing in the crowd, with my hands on her as she dances in front of me, I realize this is as much the end as it is the beginning. There she is, ready for me to fall for her, and all I can think about is how great the band is, how perfect the night is. What I realized is that I could never fall in love with her; I'm already too in love with New Orleans.

— 24, Teacher


Boston: "He puked on me."

I had been chatting with this guy on OkCupid before we decided to meet up for a date. He invited me to a Red Sox game and asked that I meet him at his place, he said his roommates would be there. When I got there, it was disgusting — like a frat house. I also noticed he had a tattoo written inside of his lip that said, "Ride or die." I know. It gets worse. When we got to the game, he let it slip that he had just gotten out of rehab. Then he proceeded to yell so loudly that we got kicked out. The grand finale? He puked on me in the cab ride back.

— 29, Corporate Hotel Sales Manager


Nashville: "He posted a Sonogram to his Facebook."

I met this guy at a music industry event in June. He was in a band but I had no idea who he was. For the next month, either he or I was out of town, but we finally went out after texting and Snapchatting literally every day, nonstop, that entire time. It was great! We talked about music and made out by my car. I wasn't even THAT turned off by his corral boots embroidered with flames.

The next week he started being super shady and backed out of a couple shows he was supposed to go to with me. Then my friend at the local magazine here forwarded me a “tip” she’d been sent about him knocking up and abandoning this girl in the UK. And pretty soon after that, he updated his Facebook with a sonogram post about how happy he is to be a dad.

I thought that was the end, but I actually saw him at a festival last weekend and he actually tried to chat me up!

— 30, Freelance Copy Editor

Washington, D.C.: "We somehow got on the topic of waterboarding."

I went out with a young woman who happened to work for an extremely conservative lobbying firm. Although we seemed to get along fine when talking about travel, our favorite places to go in D.C., etc., we somehow got on the topic of waterboarding. Although I am generally pretty apolitical, especially by D.C. standards, I do take issue with our country's interrogation methods. My date felt that we needed to do everything in our power to protect our borders and considered innocent prisoners going through these interrogations an unfortunate byproduct, saying, "They shouldn't have been there in the first place." It ended up being the reason I called things off; it seems very D.C. to say that we broke up over differing opinions about waterboarding.

— 30, Management Consultant


Atlanta: "You'd better take good care of my sister."

This girl I met invited me to a Braves game. When we met, she told me she was super close with her brother, but I didn't realize that meant he would be joining us on our date. It turns out to be a double date with her brother and his girlfriend. The pressure is on. After the game, we go to a bar where she and her brother knows everyone and they're all speaking Spanish to one another. I can't understand a word. Thankfully, we go back to her place for an afterparty. But, of course, she lives with her brother. All her brothers friends start talking to me, telling me I need to take such good care of this girl — or else. (Keep in mind this is the first date.) At the end of night, her brother says I can't go into her bedroom. They live in the suburbs and Uber wasn't in Atlanta yet, so I have to sleep in the living room until her brother drives me home in the morning. I felt like Paul Walker in The Fast and the Furious.

— 25, IT Professional

Anchorage: "It's like dating in a fishbowl."

The upside of the dating scene in Anchorage, a city of 300,000 people, is that there is a really great self-selecting crew of young people that has one big thing in common: we love Alaska and all it has to offer. It feels like it should be pretty easy to find someone who you have a lot in common with and click with.

The downside is that this self-selecting crowd creates its own super-small-town vibe. We all frequent the same few bars, restaurants, stores, and events — and there aren't that many to begin with. This makes it like dating in a fishbowl.

A couple weeks ago, I was meeting a guy for dinner. We walked into the restaurant together and immediately noticed that his most recent ex-girlfriend was sitting at the bar, just a few seats down from the only available seats in the restaurant, with her new boyfriend. I generously positioned myself so that he could sit with his back to her, and I tried not to make faces at their lovey-doveyness over his shoulder. Halfway through our dinner, my friend looked over my shoulder and his eyes got all wide. Who should walk in but MY most recent ex-boyfriend, who came over and chatted with us. And to top it off, a mutual friend of ours was watching the whole thing from a neighboring table with great amusement. That's Anchorage for you.

— 34, Lawyer

Tell us your favorite dating story in the comments below!

Photos: Stocksy and Getty Images


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