The 4 Worst Dates I've Ever Been On

I used to look at dating in New York as a pure numbers game. I figured that the more men I met up with for drinks, the sooner I'd find myself in a relationship. So I said yes to everyone, and stacked my calendars full of drink dates, walking dates, coffee dates, and dinner dates. In 2015, my mother and I deduced that I'd averaged two meet-ups a week, meaning that I'd gone on well over 60 dates in that year alone.

The benefit of this is that I've now become so desensitized to the prospect of meeting a potential romantic partner that I'm no longer nervous ahead of a first meeting. This also means that I never truly get excited by a first date — which some friends say is sad, but I just see as a recalibration. Now I know that if I'm excited for a second date, then the person in question must be extra special.

There have been some pitfalls to my mass-meeting agenda, however — mainly that I've gone on some pretty heinous first dates with men I might not have agreed to go out with had I not been so obsessed with the prospect of falling in love. But, since I strive to remain optimistic, I try to learn something from every horrible experience I've had. They couldn't have been for nothing — right?

Ahead, read the worst, wildest, craziest first dates I've ever been on — and what I took away from each experience. My overarching takeaway? Not every meeting is going to lead to your prince charming. But every date is a chance for a great party story.

After being raised on a steady diet of Disney movies, I expected to meet someone and fall passionately in love — but wound up collapsing under the pressures of modern dating. Luckily, I eventually realized that there's no "right" way to date, and that I need to find happiness within myself, no partner needed. It’s Not You is where I write to calm the voices in my head — and hear from all of you. Follow me on Twitter, on Instagram, or email me at

I excused myself to the bathroom, and just sat in the stall without peeing — trying to kill time.

The first online date I ever went on was with a guy I met on OkCupid. I was a junior in college, and having broken up with my boyfriend over the summer, decided to try my hand at the then-fringe world of internet love. The first guy who ever messaged me went by Bud*. I thought he was cute enough, and my lack of experience meant I was down to meet up with just about anyone on the app. So after a few notes back and forth, we decided to set a date.

We agreed to dinner, and since it was my first time meeting a stranger over the internet, I picked a restaurant a few doors down from the bar on the Upper West Side I was working at. Ahead of the date, I popped into the bar to let my friend and coworker Craig know what was up. Then, I walked down the block and waited for Bud outside the restaurant. When he showed up, I realized that he was at least two inches shorter than the 5'9" height he'd listed on his profile. But, trying to avoid being a heightist, I smiled, hugged him, and proceeded to follow him into the bar.

Bud was so nervous that he was shaking, and he kept playing with the candle on the table in order to distract himself. He couldn't make eye contact with me, even when I tried my best to make casual conversation to break the ice. It was the most awkward situation I'd ever been in, and I was counting down the minutes to when I could say goodbye, run down the street, and pound whiskey with Craig.The waiter swung by, and I placed my order — but Bud had been so preoccupied with the candle on the table that he hadn't looked at the menu. He asked for a few more minutes, and we filled the time with more awkward conversation and zero eye contact.

Ten minutes later, the waitress showed up — not to take Bud's order, but to deliver my pad thai. Instead of waiting for my date to place his order, she'd popped mine in solo, because this night wasn't weird enough. Bud was shaken, so he quickly placed his food order, bright red the entire time. I ordered another drink, excused myself to the bathroom, and just sat in the stall without peeing — trying to kill time away from an increasingly cringe-worthy conversation. Mercifully, Bud's food showed up quickly, and we ate in silence.

Dinner ended quickly after that, and Bud invited me for a night cap. (No, he didn't make eye contact when he asked.) I felt so turned-off from this strange, uncomfortable experience, that I faked a headache and leapt into a cab. I paid the driver $10 to drive me around the block, and then went back to the bar where I worked, where Craig proceeded to get me incredibly drunk. I swore off online dating after that — which lasted all of a month and a half.

The Lessons? Never do dinner on a first date — always do coffee or drinks. Oh, and people lie about their height sometimes.

*Name has been changed.

When we got into the comedy club, he chose a table in the front row — heckle central.

After that first online date, I decided that first meet-ups should be free from bells and whistles, and should last no longer than two hours. They really exist for one purpose: to see whether or not you two actually like each other enough to set up a second date. And I stuck to that rule — until I met Salvatore*.

Salvatore was a friend of my cousin Todd's who I'd met at a party when I was still in high school. He was one of those Facebook friends you don't remember making, but who likes every single one of your status updates. After a few years of Facebook friendship, he struck up a flirtatious conversation vis Facebook messenger, and after a few weeks, finally asked me out. He lived in NJ, and I was going to school in the Bronx, so he said he'd plan something down in lower Manhattan.

The morning of our date, he texted me to let me know that he'd bought tickets to a comedy club — and my stomach dropped. Not only do I hate comedy clubs, but that meant we'd be stuck in a bar for a few hours, and that we'd be given very little chance to talk. But, in an attempt to be agreeable, I told him that sounded great, and six hours later I met him at The Comedy Cellar in Greenwich Village. When we got into the club, he chose a table in the front row — heckle central. And, of course, during a set, one comedian asked how long we'd been dating. When we said it was our first date, he went in on us — talking about how awkward first dates were, how much sex on the first date is expected, and how tense the two of us looked sitting next to each other.

The more he spoke, the more awkward things between Salvatore and I became, until we were both sitting there with our arms crossed. I pounded my vodka sodas, praying for relief, which finally came when the show let out. I expected that to be it, but Salvatore had more plans. He took us to a karaoke bar, where he announced that we'd both select songs for the other person to sing. Cute on paper, but extremely awkward in practice. While one of us was singing, the other person would sit at the table awkwardly, clapping along, praying for sweet release — or maybe that was just me. Plus, we once again weren't given the opportunity to talk and get to know each other.

Finally, Salvatore and I said goodbye. I did go out with him one more time to a movie — his choice — but after another date with zero conversation, decided that we just weren't on the same page. I still hate comedy clubs, but have grown to love karaoke — as long as I get to pick my own songs.

The Lesson? Don't be afraid to chime in with your opinion about a date. And never choose a B2K song to sing at karaoke.

*Name has been changed.

'Are you drunk?' I asked him. 'Yeah,' he admitted. 'And I took a Xanax because I was kind of nervous.'

The second I saw Rob* on OkCupid, I was dying to date him. He was tall and brooding, with dark hair, light eyes, and a healthy amount of scruff. He wrote about his love of single-malts and Russian literature in his dating profile, and when we chatted, we bonded over our love of English New Wave music. I was heavy into the pretentious artist phase of my life, and to me, Rob was the heavily-tattooed dreamboat who would fit this version of myself like a glove.

We made plans to meet at a bar in the East Village at 9 p.m. on a Tuesday. I usually shied away from drinks after 8 p.m. on weekdays, but Rob had a client dinner, and I wasn't about to say no to my real-life Heathcliff. On my way to the bar, he'd texted me to let me know his dinner was wrapping up, and he'd be about 10 minutes late. No worries, I thought. I don't mind sitting alone at a bar and chatting with the bartender.

I roll up, order a glass of wine, and waited. Ten minutes rolled by. I texted Rob to make sure he was okay, and he said he would be there in two minutes. Another 10 minutes rolled by. I finished my wine and ordered another. Another 10 minutes went by. Now, I was seething. I'd never been stood up before, and I'd dragged my ass down to the East Village to meet this guy. Didn't he know who I was?! How dare he stand me up like this?

At this point, I was mad as hell and I was ready to go. I drained my second glass of wine, paid my tab, and was ready to go — when suddenly someone ran into my chair. It was Rob, 45 minutes late. I stared him down and barked at him: "So, what the fuck?" He apologized profusely, blamed traffic, and begged me to have one more drink with him. I relented — his eyes were broody, okay guys?

We sat down, Rob apologized again, and we got to talking. But after five minutes, I realized something was off about him — he was slurring his words, and he was having trouble focusing his eyes. "Are you drunk?" I asked him. "Yeah," he admitted. "And I took a Xanax because I was kind of nervous." Turns out he hadn't been at a client dinner — he'd been out to dinner with some friends.

That was the last straw for me. I stood up, told him to fuck off, and marched my ass out of the bar into the rain. I wish I could say I never spoke to him again, but Rob called me the next morning, apologizing profusely, asking to take me out again. So, being a dumb ass, I said yes. We dated for two years, on and off, culminating in me landing in therapy and then, eventually, screaming at him at another bar. At least there was a poetic symmetry to our time together, right?

The Lesson? Have a 20 minute time limit on waiting for your date to show. Your time is too precious to wait around for some fuckboy.

*Name has been changed.

I joined the nefariously-named Yes, such a place exists. And it is hell.

I come from a family of Republicans, save for my youngest brother who considers himself an independent. He didn't vote in the last election, but my mother, father, and middle brother all went to the ballot box for Donald Trump, leaving me the lone Hillary Clinton supporter in the house.

This has caused more than a little bit of tension in my family, even in parts of my life that I never expected it to — like my dating life. After the election, I announced that I'd never date a Trump supporter, to which my mother said I was limiting myself. "Why would you turn down a guy based on his voting record?" she asked. "It's a fundamental difference in values," I replied. She was not convinced. So, stubborn as I am, I told my mother that I would go on one date with a Trump supporter, just to prove that I was right and she was wrong.

Since finding a self-admitted Trump supporter in a city like New York on normal dating apps would be harder than finding a livable studio apartment for under $1,200 a month, I joined the nefariously-named Yes, such a place exists. And it is hell. I passed myself off as a Trump supporter by repeating words of praise my parents had for him, and matched with Aaron* a cute, hipster-looking guy with tattoos who, had I seen him in a bar, I'd never have pinned as a Republican.

After faux-lamenting over the prevalence of "snowflakes" on typical dating apps (I deserve a literary award for the fiction I wrote), we made a date to meet for a drink at a bar in the West Village. When I got to the bar, Aaron was there — well-dressed with Buddy Holly glasses and a full sleeve ofd tattoos. Looks-wise, he was my type. And after 10 minutes of small talk, I felt myself warming up to him. We had similar tastes in television shows and movies. He was well-traveled and well-read. He had a fantastic smile and a better laugh. Could mom be right? I wondered, sipping my wine.

But the conversation quickly got political, and the whole scene fell. Aaron went on and on about how "PC culture was ruining this country" and how the "fake, liberal media" was the reason Trump's approval rating was so low. He blamed Barack Obama for racism. He said that if the DNC wasn't so obsessed with Hillary and actually allowed Bernie Sanders to be the nominee, liberals would have won.

I was horrified, but sat smiling and nodding, trying to play up the charade. Every time I tried to steer the conversation away from politics, he'd yank it back. After one drink, I had to get the fuck out of the bar. I was sitting across from everything I hated. So I thanked Aaron for the drink, said I had to meet friends for dinner, and gracefully exited the bar. When he followed up for a second date, I told him I didn't feel a strong connection, but to be well.

Now, I know that not every Trump supporter is going to be as hardcore as this guy. I know that my mother suggested I taste a slice of cake, and I wound up eating an entire bakery worth of crazy by finding a guy on But I couldn't help but feel a tiny bit smug when I texted my mom the next morning, "Looks like I'll be sticking to liberals."

The Lesson? Mom isn't always right.

*Name has been changed.

Related Video
Load more...