Dating Disaster: I Met A Guy Who Cried On Our Very First Date

annoyed girl

Once upon an OkCupid message, a dude named Andrew messaged me.

His message was charming and thoughtful, unlike the many (sarcasm intended) 'Yo baby, wasssssup' spams I get and frankly never understand because, does anyone respond to that?! Anyway, we did the flirty back and forth text tango for a day or so before he asked for my number. I made him give me a pickup line for it, he went with the cheesiest one, and I smiled at my desk at work when I read it.

Two days later, we were finally setting up our first date when he suggested a well-known, old school Italian joint in the West Village. I had always wanted to go but could never afford it, and it felt really odd accepting such a generous offer from someone I hadn't technically met. But he was tall and had a great, interesting job and we seemed to like the same things, so I gave in and made an off-hand comment insisting I'd buy him drinks after dinner.

I wore a red dress I got at a sample sale with some pretty tall heels (he said he was 6'4"!), and I arrived just a few minutes late, finding him sipping on a dirty gin martini at the bar. I was instantly intrigued; it's my favorite drink.

"You must be Lindsay," he asked. I nodded and took a sip of his martini, thinking there must be fireworks already. Instead, he looked at me oddly and pulled his drink toward him. I figured he must have forgotten our conversation about sharing the same favorite drink and I wiggled in next to him. But before I could say anything he continued, "Well, we should get our table. I'll close out. Um. You look, um. Nice."

I gave him a half-grin, and we retreated to a romantic corner that was nestled between other couples. I felt really out of place and started to question if maybe I made the wrong decision about agreeing to a dinner date instead of the safe happy hour drink near a fire exit. But after he ordered us an expensive bottle of wine and began knocking back glasses much faster than me, he loosened up.

Loosened up a lot. Too much.

When our pasta arrived, he took a few bites before saying, "I have a maybe-inappropriate question for you." I nodded, purposefully stuffing pasta into my mouth politely so I'd have more time to think. I was ready for anything: something about sex, something about if I shaved or not, something about going back to his place, something about my long-lost cousin twice removed he used to know. (Really, NYC is an odd place to date.)

"When was your last relationship?" He asked, his stance doe-eyed, his face suddenly flushing red. Thinking this was an interesting turn of events, I answered honestly that it had been two years at that point since my last relationship, then asked him the same question.

"Like three weeks ago. We dated for five years. I really thought I was going to marry her," he answered. "She was really amazing and I'm not sure what happened. She said we never did fancy things or went anywhere fun, but we lived together, ya know? It just changes things. I mean, not to say I wouldn't live with anyone again, I would. I mean, if you and I worked out, I could totally be okay with a dog. Lucy [my dog] seems cute. But anyway, I don't know. I'm dating again. I'm trying. It's really hard. Do you think it's hard? You must, since you write about it. I just think about her all the time…"

...and then he started crying.

Over his noodles. In the middle of one of the most beautiful restaurants in New York City that has an ambiance that makes you want to get naked and costs, like, $30 a plate for fettuccine. And this wasn't just a runaway tear he could brush off his face. These were goblet-sized tears that usually flush down a screaming toddler's cheek in the middle of a crowded grocery store because their mom won't buy them candy.

As people started to look over at us and he continued to rambled words I couldn't understand through the blubbering, my instincts kicked in and I started rubbing his arm, reassuring him it would be okay and that he probably just needed some (read: A LOT) of time to process through everything and that maybe not all hope was lost for the relationship. I might have even offered to call the girl myself if it would make him stop crying, but after a few minutes (which felt like an hour), he excused himself to the bathroom.

I considered making a run for it, but I finished my dish (I really wanted to eat there, damn it!), poured myself another glass of wine and looked straight ahead so I couldn't see the death glares from the other patrons who surely thought I had just broke up with my cute boyfriend. (If they had known it was our first date, they probably would have bought me more vino.) After he returned, he grabbed the bill, boxed up his food, and didn't say much until we reached the subway.

"I guess I'm not really ready to date yet, am I?" He asked. I gave him a hug and told him that if he was serious about that girl, then he should bring her to that restaurant and see if maybe she would change her mind. And if not, to give dating a rest for at least a few months. I took the local train home that night, and I thought about his sad eyes and how embarrassed he must have been to cry in front of me. I was glad I was kind to him (karma!), but I also made a decision from there on out:

I'll never agree to dinner on a first date ever again.

It's too much time to spend with someone you don't really know. And for dates that do go well, it takes some of the mystery out of the chase—it's exciting to haves drinks progress to dinner progress to a day date progress to sex (and maybe love eventually). And if it's a bad one, well … let's just say there really isn't anything worse than a grown-ass man in a suit, sobbing over red wine sauce and moaning about his ex-girlfriend.

So heed my advice. Just suggest drinks. Trust me.

Lindsay Tigar is a 26-year-old single writer, editor, and blogger living in New York City. She started her popular dating blog Confessions of a Love Addict after one too many terrible dates with tall, emotionally unavailable men (her personal weakness).


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