Dating Three Girls at Once
Their names were Lily, Jade, and Kim. I preferred them in that order.
At one point in college, I was dating three girls at once.
I’m not bragging. It was not cool at all. This is the kind of shit that kept me too busy to decide what to do with my life.
What kept me even busier: my insistence that none of these girls should ever find out about each other. We weren’t technically in “relationships” per se, but I was operating under the assumption that normal girls are only really capable of loving one man at a time. And tragically, that man happened to be me, though “man” is a stretch; I was more of a a love pit.
Their names were Lily, Jade, and Kim. I preferred them in that order. I mixed up biographical details about them constantly, a result of my inability to compartmentalize these relationships—or perhaps I just wasn’t really paying attention in the first place.
My entire life at that point was a kind of performative juggling act, equal parts desperation and delusion, the kind of thing you could only really get away with at 19, when the consequences of your actions still seem abstract and distant, if they exist at all.
I met them all on Tinder. That’s where I meet every girl. I’m too sensitive and kind to bother girls in real life. I only want to talk to them if I know they want me back. There are many sensitive young men like me out there, I’m sure.
Lily was a transfer student — things didn’t go so well for her, socially, in her first year at Dartmouth and so she decided to hit the reset button and start over on the other side of the country. She only told me this months into our relationship.
Lily was the most like me. She was quiet and curious and secretly full of love. She too was a direction-less wordcel: “pre-law” is what we used to call ourselves. She would have been good to me, maybe, if I didn’t fuck things up so bad.
Jade was not quite as hot as her tinder photos led me to believe, just barely hot enough to keep my attention, but she, too, had a heart of gold. If she had ever let me smash, I probably would have ghosted her right there.
She was the most cautious, principled, of the three. More deeply in love with me than either of the others. I was a little out of her league, physically, which I say not with pride but with a kind of detached observational quality, as if noting the weather. She was a go-getter, involved in several university clubs whose names I’ve since forgotten because I never really cared in the first place. She had socially conscious roommates and an impressive array of succulents that she watered diligently, every day.
and Kim was kind of a bitch. Kim loved to talk and hated to listen. Kim loved talking so much she didn’t realize she had not learned anything about me, which was convenient— because I really was dating three girls at once; that was the activity that occupied most of my time.
She wasn’t all bad. She was into eSports like me. She was an artist—she made cute stickers. She made things and sold them, and I admired her for that. She was loud and made deep eye contact, which intimidated me a little. I could tell she would be the jealous type. I was heavily intoxicated through most of our dates. She didn’t like weed and gave me shit for being high. She made me regret being momentarily honest with her. But she fucked me anyway.
Kim saw me shirtless for the first time and said “you need to wear tighter shirts,” and it took me almost 6 years to un-internalize that. Kim was the first girl who really took it upon herself to fuck me. I didn’t have to coax her into it; I didn’t have to plot my way into her apartment, nothing. She took my clothes off and she put the condom on me and she really fucked me. I don’t remember if the sex was any good. Everybody in college had a Twin XL bed, so it couldn’t have been that comfortable.
It all came crashing down when Lily and Kim found out about each other by hilariously unlucky happenstance. At a University of 34,000 students, these two females happened to have a mutual friend who introduced them so that the three of them ended up in Kim’s apartment one day talking about “boys.”
Here’s the horrific scene as Lily later relays to me: They’re talking about guys they’ve hooked up with at school, or maybe just Kim’s talking about it, and she describes an experience with one “James” she met on Bumble a few weeks ago, who is later revealed to be a “eSports Player,” which pretty much confirms it’s me and makes Lily feel like she’s being punched in the face, because she has been hooking up with this very same gamer with a steadily increasing degree of intimacy for the past couple of months. But she’s duplicitous like me, so she does not mention this to Kim in the moment.
At our next meeting, Lily asks me if I’m hooking up with other girls, and I think, there’s no way, at a school of 34,000 people, she has somehow confirmed that I am privately seeing other girls (remember, I was stupid). I can tell from the look on her face that she would be really sad if I said yes, and I think it’s a genuine question, so I lie to her and say no.
I didn’t think much of it— I just did a quick calculation of the risk-reward and chose the option most likely to make this go away. If I say yes, we’ve definitely got a problem, and if I say no, there’s a very high chance that nothing ever comes of this.
She eats my lie and pretends to accept it. I think: disaster averted. All is well. We do what we do, I leave, and start to think more seriously about the situation.
I don’t have much time to think because that night I receive several harrowing messages from both Lily and Kim… while I’m out roller skating with Jade, who is perfectly oblivious to it all.
Lily went back to Kim to confirm, and K questioned why L might have such a strong interest in knowing this information. So now they both know, and my Facebook Messenger DMs are a war zone. I cannot revisit those messages and probably will not do so, ever.
I go to see Lily again in a day or two and after a lot of crying and angry touching I am able to communicate to her that I Didn’t Know You Wanted To Be Exclusive, And We Can Do That If You Want Because I Like You More (a truth that was as much a confession as it was a final attempt to salvage something from the wreckage). With mixed feelings, she accepts this. And that was the foundation of my first relationship.
And instead of informing Kim, who was always kind of unlikeable anyway, I simply ghost her. She messages me a couple times, and I give bad responses, and she says some mean things about Lily. I try to make Lily feel okay because I like her more. Kim probably comes away from the experience thinking I’m a “bad person,” and she’s right.
As for Jade, who was always nothing but positive and kind, she got an extended cold shoulder which finally froze when I just stopped responding to her, too.
Her last message to me was asking when she could see me again to give me my birthday present. I really wish I was making this up.
At no point did I say: “I’m with someone else now, sorry,” because I couldn’t bear any kind of bad news, ever, to anyone. Ironically, this near-pathological aversion to confrontation caused so much more suffering all around than if I had just been upfront about everything from the start.
But then there would be no story. So yeah, live and learn. And hurt as many people as you can in the process.
You should try dating 4 simultaneously 😏