I Had A Crush On My Best Friend’s Brother & This Is What Happened

Eric* leaned in to kiss me in the hauntingly bare common area of my freshman dorm room. I stared back at him like a deer in the headlights, if only the deer had been cross-eyed and had its arms fixed stiffly at its sides. The kiss was about two-seconds-long and mmm, I'd say exactly two seconds too long. In my head, I was already thinking of an exit strategy, not from the kiss but from whatever this would turn into. You see, even though I'd gone out with Eric that night in November, I knew I had a crush on my best friend’s brother, Michael*.

The only problem was that Michael was almost 10 years older than me, which I figured would be a huge downer on my freshman experience. Wait, there were two problems. He was also in a toxic, on-again, off-again relationship with his girlfriend of six years. Fine, three problems. He lived in my hometown, in an entirely different country. OK, I think that covers it.

So, Eric. He was a stand-in. I hadn't decided for how long or how many stand-ins I would need exactly but my thought process was as clear as the Red Bull I chugged before going on this date. I would spend my college years dating while Michael worked through his relationship issues back home. Then, when I returned after graduation, he would see me for the sophisticated, worldly being I'd blossom into. Duh.

That is, of course, if I made it home alive. Eric proved to be more of an obstacle than a stand-in, really. Here's how it all went down.

Eric and I had exactly two things in common. We were in the same section of freshman music appreciation and we lived on the same floor of our residence hall. Both of these situations presented endless opportunities for the movie-inspired meet-cute of my dreams but, alas, that is not at all what I got. I mean, I've heard of actors veering off script before but, holy hell, this was next-level. Our meeting that November of my freshman year still holds its rightful place in my top five most embarrassing moments. And for context, let me just say that I drunkenly attempted to disrobe in a parking lot last weekend.

It was a Thursday night and my three roommates and I — all covered head to toe in glow-in-the dark paint because college — piled into the elevator of our residence hall to paint the town... well, these colors.

Sydnee Lyons

That's when Eric fluttered in like a moth to a neon flame and, all in one breath, asked me to go out on a date with him that Friday. I felt ambushed and unfairly obligated to agree, so I did, but our date was just as awkward as our introduction. That's right — the first time he asked me out in a public forum was also the first time he had ever spoken to me. And TBH, I wish it had been the last because on the actual date, he uttered these magic words while grazing his fingers against my shoulder: "I just love the touch of a woman's skin." Like, WTF!

The night was a bust, obviously. After he left, I locked myself in my room so I could Skype my hometown BFF Kristie* to tell her all about it. She was just excited to hear I'd been on my first college date — so excited, in fact, that she told her mom and all three of her siblings. The thought made me a little queasy because, like I mentioned, I was working on a long-term plan to woo her older brother. Luckily, none of them reached out to me to tease me about it so I thought, "Eh, all good."

Still scarred by my near encounter with Silence of the Lambs' Buffalo Bill, I was up late scrolling through my Facebook feed when I saw it.

Michael had posted a status update (remember when those were cool?) about how he'd gotten his heart broken by a girl who didn't even know it.

Umm, who's this about? Did he get back together with his ex again? Ugh, I'm going to have to go to this wedding, aren't I?

Wait, does he mean...

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The more I thought about it, the more I realized how badly I wanted it to be about me. Don't get me wrong. I didn't want to be the girl who hurt him but I wanted to be the one he cared enough about for that to be possible. Maybe the one who went on a date with someone else recently? I had to know.

I slid into his DMs (although, I definitely didn't call it that in 2009) and boldly asked if his status was about me. I knew it was. It had to be, right? Right?

We'd shared glances when I took over his living room on a weekly basis to host study groups with Kristie. And there was that one time he pretended to be my date so no one would hit on me because I was already having a crappy day. It's just that, I figured it would be years before either of us admitted we had feelings for each other. There was the age difference and the family complications and the distance and just, literally everything else that made it seem not only impossible but also ill-advised.

"So what if it is?" A text bubble appeared around three in the morning. "Then you should tell me," I quipped back without hesitation. "Because I'm meeting someone for a second date tomorrow. On his boat." Eighteen-year-old me felt the location was important because, hello, I was literally about to sail off into the sunset with another guy. (Full disclosure: I most definitely was not.)

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But Michael didn't need to know that. My little white lie worked. He admitted that the status update was about me. I swooned.

We stayed up talking for hours that night and almost every night after that for the four years we were together.

I'm not going to lie. It was awkward at first — not between us but for the people around us. I'd been friends with Michael's sister for about seven years by this time and our families knew each other exceedingly well. So, you could probably guess that my parents weren't thrilled to find out that the only person they trusted to take Kristie and me to a nightclub for the first time (I grew up in the Caribbean, where the legal drinking age is 18) was now my boyfriend.

It was this weird dichotomy where they truly trusted him with my life, just as long as we absolutely were not dating.

I'm not sure where I got the gumption to do this, but I decided that Michael and I would proceed as if everyone was as excited about it as we were, until they were, and it worked. It's been more than five years since we broke up and my parents still openly talk about how he was the best guy I've ever dated. Thanks, Mom and Dad. I'm glad we have similar taste in guys? I don't know.

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Obviously, similar taste in guys wasn't something Kristie and I had in common since, you know, I dated her brother. She never openly questioned our relationship, but there were times I felt like it pushed us apart, particularly toward the end of it.

Michael and I had one of those year-long breakups that lingers way past the actual expiration date of the relationship. No one cheated, or fell out of love, or anything dramatic like that. But, being almost 10 years younger than Michael was, I felt like I needed to go off on my own for a while. I'd gone from living at home with my parents to living in my college dorm where I Skyped my hometown boyfriend every day for four years. In a lot of ways, dating my best friend's brother was what kept me feeling close to home when I felt most alone.

You could say that Kristie was kind of like our lifeline. So, when Michael found out that I'd moved on more than a year after our breakup and that she'd neglected to tell him, he took it pretty badly. I could feel the cosmic shift in my friendship with Kristie almost instantly. In trying to support me as a friend, she'd failed him as a sister and now, she had to do major damage control, which meant not-so-subtly implying that I should remove myself from the equation.

It always comes back to high school math, huh? If I was going to be seeing other people, I needed to cut Michael off for good.

Looking back, I don't blame Kristie for taking sides because I would do the same for my brother. But now, when Kristie and I speak, it's in vague generalizations about how our lives are going — the weather, apartment woes, and any noteworthy career changes. When we talk about our families, we acknowledge very quickly that everyone is doing well. She never mentions Michael by name and I never ask.

Some people say that dating their best friend's sibling makes them feel that much more like sisters. If that's the case, then Kristie and I have become those estranged sisters who socialize only on occasion (at weddings and family reunions) and who feign European cheek kisses in passing. OK, so it's not exactly like that but it sure feels like there's more space between us than ever before. Maybe that's because Kristie, Michael, and I all live in different countries now and maybe that's the way it should be.

*Name has been changed.