Park Sloper fighters and Cobble Hill gropers: The 5 worst Brooklyn dates I’ve ever been on

Fighting an old guy is never a good idea. Especially when you're on a date.
Fighting an old guy is never a good idea. Especially when you’re on a date.

I happen to be a Brooklyn dating pro, because I naively choose to believe that I will find my love and together we will ride a tandem bicycle into the sunset, which in turns means that I go on an absurd number of dates. My (nearly) 10 years of dating in this borough has had its perks as well as its disadvantages. Perks: Being privy to the particularly bad dates that plague Brooklyn, I know the warning signs and can hope to avoid them in the future. And sometimes I get to make out with a cute guy. DisadvantagesI must endure the dates at all.

Despite the optimism that someday my hipster prince will come, I realize my dating record doesn’t speak highly of the kinds of guys who remain single in this borough. (I know men have it hard, too, but their dates generally aren’t as creepy and violent.) I have been on far worse dates than the ones mentioned herein, but please allow me to share with you the five worst dates I’ve been on in Brooklyn. Because if others can learn from my experiences, at least some good will come out of it. And so, from worst to most worst:

5. 20 (inappropriate) questions

Via Giphy.
Via Giphy.

Malcolm was an OkCupid match about seven years ago. I invited him to meet me at Lobo (if you’ve ever dated me, I’ve probably taken you to Lobo) for my favorite drink: a cinnamon and blood orange-infused margarita on the rocks called Sangre de Lobo. It’s glorious and you should try it, sans the painful date that followed.

The date was going remarkably well, until I allowed Malcolm to speak. If a date ever asks you any of the following, it’s probably a good indication that he doesn’t have a lot of awareness for acceptable social encounters with strangers/anyone:

“What is the most you’ve ever weighed?”

“Is your mom hot?”

“How many dates do you go on before sleeping with someone?”

“Are you having a good time?” (Repeatedly. Like, every 10 minutes.)

These are just a few of the gems Malcolm asked me within an hour of our meeting. Asking your date questions is a great way to get to know them. Asking your date wildly inappropriate questions is a great way to make them wish they were anywhere else.

4. Reinventing the third wheel

Via Giphy
Via Giphy

We’ve all felt like a third wheel before, but few of us have voluntarily invited ourselves to be a third wheel on an actual date.

There’s some important background information to the characters in this story, so allow me to set the scene:

Kevin: A name I’ve chosen to protect the innocent. I went on a date with Kevin, another OKC match, a little over a year ago. He was nice; it was a fun evening, but nothing came of it. A month later I was using Timehop and saw him in pictures with me from a friend’s birthday party that took place two years prior. We had been placed on the same scavenger hunt team and spent the day together, but neither of us remembered the other and made the connection before or during our date. I reconnected with him after making the discovery, and we are now good friends who used to frequent bar trivia together with a larger group of friends.

Greg: Host of the trivia night I once frequented.

So there I was, hanging out with my friend Kevin at trivia night. I’d been dating Greg, the trivia host for a couple months and Greg and I had a standing date every week after trivia. On this particular night, Kevin asked if he could join us. We went to Rucola when trivia was over; just me, Kevin, and Greg. I sat in the middle and enjoyed being ensconced by two handsome men, but looked forward to being alone with Greg so we could make out. Kevin and Greg started trading stories from their mutual home state of Massachusetts, and I started feeling like the third wheel. When Greg and I were finally alone that night, he broke up with me, turning an awkward evening into a really fucking terrible night.

Maybe Kevin should have stuck around to keep us balanced … if only third wheels also protected fragile hearts.

3. Open window = open invitation?


I honestly don’t remember where I met Chris, the first person I went out with after moving to NYC, but it was some dating site long ago. He was very tall, had blonde hair, was a chef, and I think he was wearing cowboy boots. I was coming from a pretty negative dating situation (to put it mildly), so I had high hopes that things would be better this time.

After hours of drinks in multiple watering holes on Court Street, Chris telling me he couldn’t wait to introduce me to his mother, and offering to make me breakfast in the morning, he walked me home and I invited him upstairs. Soon neither of us were wearing clothing. Cue Charlie. Charlie was my neighbor’s cat who had wandered in through the window.

Cue Jordan, Charlie’s owner.

Jordan stuck his head through the window. Chris and I sprang up from our spots on the sofa, and huddled together in a corner, as far from the window as we could get, but totally uncovered. Jordan asked if anyone had seen Charlie. I replied that, yes, I had seen Charlie come through. Jordan, who I hadn’t met yet, then proceeded to make small talk: “Hi! I’m Jordan. Are you new here? I’m sorry we haven’t met before. Where are you? Why can’t I see you? Where’s my cat?” etc.

I excused myself to retrieve Charlie and somehow managed to pass him back through the window without Jordan realizing I was naked. Apparently I had some pretty awesome curtains. Charlie safely returned to Jordan’s loving arms, Chris got dressed and departed.

The next morning, still wanting breakfast, I called Chris: “Hey, I’m on my way. Remind me where you live.”

I had clearly just awoken a groggy Chris, but he gave me his address and I continued on my way. Despite inviting me over and telling me where he lived, he still looked surprised to see me when I showed up at his door. “You really want breakfast?” Well, yeah, that was the deal. He made me toast. Toast. He managed to fry one egg as well. I browsed his DVD collection and we then cuddled and watched the incredibly romantic severed-head film Seven, after which I never heard from Chris again.

2. Let’s not get physical

Via Giphy.
Via Giphy.

Raj and I met at Union Hall after a mutual acquaintance suggested we might be a good match.

It began with 45 minutes of awkward conversation including a political argument in which he defended Donald Trump and assumed I wasn’t intelligent enough to defend my own political perspectives. Later he made loud choking sounds and mimicked vomiting when I casually mentioned cottage cheese. Raj then suddenly launched himself across me at the person I hadn’t even noticed was sitting on my other side. I turned and saw a man at least a decade older than my parents (so, at least 70).

“Hey, man, what do you think you’re doing? You got a problem?” Raj shouted.

The man said, no, he was just trying to look at my tattoo, sorry if he offended anyone. Incredulously, I realized Raj was starting a physical altercation because another man looked at me.

I voluntarily showed the man my tattoo, which is on my forearm, by the way, not my breast or anywhere else a strange man shouldn’t be looking. He said it was pretty lucky that he was an easy-going guy; the next man Raj accosted might not be so understanding.

Raj: “You want to tell me what you think might happen then, huh? Why don’t we go outside and you can show me?”

Man: “No, I’m just saying, someone else might not be okay with this. The way you’re acting; you are definitely not from here. This is not how we do things.”

Raj: “I was born and raised in Brooklyn, man! You don’t believe me? I’ll show you how we take care of things in Brooklyn.”

And so on. I  grabbed my purse and coat, told Raj his aggression was scary and totally not okay, and my Brooklyn Bridge tattoo and I hightailed it out of there, shaking. He did later text me to apologize and say that he’s trying to leave his anger at the office but it had been a really rough day. Guess what? Work is hard, deal with it. A bad day is not an excuse to be a male chauvinist or try fighting a senior citizen over Brooklyn pride.

1. Blind Date Ambition


Mike, a blind date that was arranged eight years ago by my boss at the time (in the Children’s Department of Barnes & Noble) showed up 30 minutes late to our date at Cody’s because he lost track of time while out with friends. He showed up at 8:30 p.m., already stupid drunk. I should have made my exit then, but he was cute, bespectacled, and was just grown-up Harry Potter enough to be my type, so I decided to give it a shot. My boss friend had told me that Mike said he was “looking for more than just another wet hole,” so obviously, this guy was a catch. But then Mike ordered another strong cocktail, at which point he began to make me extremely uncomfortable by raving about how beautiful I looked. I appreciate a compliment as much as the next girl, but it was hard to detect sincerity through the haze of alcohol clouding his vision.

Then Mike ordered another drink, at which point he tried to lure me back to his apartment with the classic line, “I’ve got some great music on my computer I want you to listen to. My computer’s in my bedroom, by the way.”

I transitioned the conversation back to small talk, and that worked for a bit, until Mike ordered another drink. Then he walked over to me and shoved his hand down my shirt.  I was sitting in a restaurant, with people at tables surrounding me, with a drunk asshole who had now worked his hand into my bra. I honestly don’t remember what I ended up saying to Mike, but it was along the lines of “Get your stinkin’ paws off me, you damn dirty ape!”

He returned to his chair, threw it to the ground and stormed out, leaving me with a bill for $70 that was primarily his drinks. It should also be noted that he actually hit me with the thrown chair. Our waitress came over after he was gone and asked if I was all right. I still got stuck with the bill, but at least she brought me a drink on the house.

I had a text from Mike before I even got home that night that simply said, “Had a great time tonight! Let’s do it again soon, babe.” I don’t think it was a joke.

To be fair, I’ve dated some truly “great” men, like Jonny, the music promoter and blogger who made me a break-up playlist after four dates (I’ve forgotten what he looks like but the music lives on), and Nick, the unemployed attorney who lived in his parents’ basement, who brought me a box of Thin Mints when he broke up with me after a year of dating (“The fact is, I never loved you and I never will. Here, have some cookies”). But to break up, you have to jump the first date hurdle, and that’s often the hardest part of all.

The last date I went out with showed up in sweatpants and his own band’s t-shirt “for publicity.” I’m beginning to learn to spot the warning signs, but my problem is that I believe everyone deserves a fair shot. I’ve now learned to take advice from a trio of my Brooklyn brethren and Fight for my Right (to be treated with respect).

Follow Margaret on Twitter for more dispatches from the dating trenches: @askmemargaret.

Got a bad Brooklyn date story you think tops these? Tell us in the comments!

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