If two years ago you told me I’d start dating my closest guy friend from college, I would have never believed you. We were always super close (going to the same parties, studying in the library, suffering through dining hall breakfast), but in a platonic, group-oriented way. After graduation, we kept in touch really well, making time to see each other one-on-one and catch up. For a while, I didn’t think anything of it. We were just two pals, being buds! But slowly, as the leaves began to change and a cold breeze swept the city, I realized the unthinkable: I had a crush.
Apart from my student loans, this was possibly the worst thing happening to me. In a way, the crush was worse than the loans. (Okay, dramatic, but at least you know what to expect with student loans!) Crushing on your best friend felt like forbidden, uncharted territory. Not only was I worried about losing the friendship, but the thought of potential rejection also stung. Would I ever recover if he didn’t feel the same?
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I remember actively stressing about my feelings and trying to squash the crush at all costs. It was only when my sister directly confronted me — “What, do you like him or something?” that I finally admitted my deep, dark secret to someone: I had romantic feelings for my best friend.
Thankfully, this story has a happy ending. After a long autumn of mulling over my next move, I finally admitted my feelings to my friend. I was happy to find out he was asking himself the same questions. We’ll call him SO, because he ended up becoming my significant other. I’m so happy we took the leap to more-than-friends, but it didn’t happen overnight. If you’re considering moving from friendship to romance, here are some ways to discern your next steps:
Decipher whether your feelings for your best friend are “comfort” or actual romantic interest.
When you’ve been friends with someone for a long time, you can be yourself around them in a way you can’t with someone you’ve just met. Being friends first eliminates guesswork about things like relationship history, self-care habits, willingness to binge-watch “The Office,” etc. Comfort isn’t a bad thing, but it can potentially cloud a crush. Are you interested in your pal because they’re the safe option (they’ve already seen me cry! I can wear sweatpants to their apartment!), or do you genuinely see potential with this person?
Try this: Think about someone you once had a huge crush on. If that person arrived at your door with flowers, would you jump into their arms, or close the door and call your friend? If you’d pick your friend over them, maybe your crush is legit.
Pay attention to behavior changes in both of you.
This was something I thought about often during the early days of my crush. Was I mislabeling affection as interest? Do I like-like him, or do I just care about him a lot? A little green monster called jealousy helped me figure this out. On nights out, I would wish for my crush to be there with me. And when he was at parties, I found myself wishing that I was there and wondering who he was with. We used to easily complain to each other about our dating woes, but gradually, I found myself avoiding those conversations with him. These changes helped me realize that maybe my feelings for SO weren’t platonic anymore.
As for interpreting their feelings — trust your gut. You know when someone is showing interest in you (even if it’s just the slightest spidey sense) so pay attention to those cues and give them room to unfold. But bottom line, unless you directly ask your pal, you can’t infer their feelings with 100% accuracy. Pay closer attention to shifts in your own behavior over time.
Do a risk assessment on your friendship.
This was a pain point for me during my crushin’ days. I cared so deeply about our friendship, and I was terrified of losing that relationship over a couple of dates. We share the same group of friends, so I agonized over whether or not a changed group dynamic would be awkward forever.
Take inventory of your relationship with your pal, prioritizing long-term fallout over immediate gratification. Ask yourself, if you had to wait one month from today to act on your crush, would you still want to? Look beyond the honeymoon phase of rooftop dates and dinner party plus-ones and really consider what a relationship with this person would be like in the day-to-day. And even though it’s tough to imagine, consider the possibility of it not working out. How would that impact your life or your friend group? Are these feelings strong enough to warrant the risk?
If you’re still in doubt, just give yourself time. Continue cultivating and strengthening your friendship, while remaining open to other possibilities. If nothing comes out of the crush, you will at least emerge with a better knowledge of yourself, your friendship, and the wonderfully weird world of crushes!
Originally published on February 5, 2020.