it's complicated

What Happened When My Friend and I Confronted the Guy Who Was Texting Us Both

Illustration: J.V. Aranda

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“I’ve been talking to this really cute guy on Tinder.”

I was sitting at a bar on the Upper East Side one Saturday night with a friend I’ll call Ally. Like me, she was waist-deep in the polluted swamp that is online dating. And considering the fact that we’d each just obliterated our third glass of wine, it was time to start talking about it.

“What’s his name?” I asked. When she told me — I’ll call him Colin — my ears immediately perked up: I’d recently been talking to a cute guy on Bumble, also named Colin. When I told her as much, she immediately whipped out her phone to compare notes. Lo and behold, we were talking to the same guy, who, it appeared, hadn’t even gone through the trouble of changing up his profile between apps. His photos were even in the same order — the ski suit followed by the group shot followed by the laughing photo.

This didn’t come as a complete surprise to me. Not only was I aware of double dipping in the world of online dating, I often participated in it, dating multiple guys at a time until things got serious with one. My friends and I, when comparing notes, would sometimes realize that we’d spoken to the same person at different times. But I’d never been sitting right next to a pal when we realized that we were both talking to the same guy at the same time.

Colin wasn’t even good at playing the game. He was the type of guy who wouldn’t set an actual date — instead, he’d text you at 8 p.m.
on a Friday to see what you were up to that night. Ally and I started comparing notes, and realized that he’d messaged us the exact same things — verbatim! — at the beginning of each of our respective conversations. “What a fuckboy,” Ally said. And I agreed: I’m cool with dudes chatting with multiple women at the same time, but to be that lazy in your messaging? That’s where I start to judge.

Now on the fourth round of wine, Ally came up with a great idea: “Why don’t we both text him at the same time?” It was the exact kind of scheme that you’d think was completely hilarious in high school.
But bolstered by the haze of booze, Ally and I were rolling.

The texts started innocuously enough. At the same time, we both texted him asking what he was up to. Colin answered me first, telling me that he was downtown at a bar with a friend of his. He invited me to come. Two seconds later, Ally’s phone buzzed with the exact same message. I quickly fired back: “Sure! That sounds like fun. Which bar?” Ally followed suit, telling Colin that a meet-up sounded great, and which bar should she meet him at?

There was a lull, during which time Ally and I cackled with excitement. Then my phone buzzed — a message from Colin.
“Actually, I can’t meet up tonight. My friend is taking me to a party at someone’s apartment.” Thinking that he’d discovered our ruse, we expected Ally to get a similar message. Instead, when her phone buzzed, he sent her the name of the bar he was at. Well. He’d made his decision.

“Oh, we are so going to this bar together,” Ally said. It seemed like the most hilarious thing in the world, so I agreed, paid our tab, and we jumped into a cab. On the ride to the bar, we shared our adventure with our cab driver, wiping away the tears that rolled down our cheeks with laughter. We were going to nail this asshole, and it was going to be the funniest shit in the world.

In my mind, Ally and I strutted into the bar like Beyoncé. But given the fact we’d drank roughly a bottle each, it was probably more like a stumble/sway walk that brought us face-to-face with Colin. Ally went up behind him and tapped him on the shoulder. He spun around, looked at both of us, and started laughing. “I knew it,” he said. Then Colin ordered us a round of drinks, and we had a good laugh about it all.

Ally and I continued to razz Colin as we drank, and he seemed like a good sport about it. After we finished our rounds, he invited us up to his apartment with his friend. “I have this great bottle of wine we should open,” he said. Ally and I were wasted. We said yes. But by the time we got to Colin’s apartment, his friend had disappeared. Colin opened the bottle of wine, poured us each a glass, and asked us to join him on the couch.

We drank and talked for a bit. And then Colin kissed Ally. He then looked at Ally and I in way that immediately conveyed what he was up to: this guy was trying to turn a situation in which two women called him out for being an asshole into a three-way. I wasn’t about to wind up in some letter written to Penthouse. The energy in the room shifted with our visible discomfort, so Colin suggested we watch a movie. When he suggested Midnight in Paris, Ally hit the roof.

“I am not watching a Woody Allen movie!” she screeched. (We’d had a lot to drink at this point.) I burst into laughter, and then realized I had to pee. I ran into the bathroom to relieve myself, and when I got out, Ally was gone. “She stormed out,” Colin said.

Laughing, I collected my stuff, told Colin thank you, and made my way to the door. “Don’t you want to stay?” he said. I told him absolutely not, and that he should probably be more mindful about his messaging game. “It pretty much sucks,” I said. Then I walked out the door.

The next day, through our hangovers, Ally and I rehashed the evening. We came to the conclusion that middle-school games are only funny in middle school. But still, ever since then, whenever I went out with a man, I’ve always wondered a few things: Is he messaging other girls the same things? Is he secretly a Woody Allen fan? And will he try to work me into a three-way?

My Friend and I Confronted the Guy Who Was Texting Us Both