Dear Di

How to manage catching the feels for your best friend. Illustration: Rame Abdulkader.

Dear Ty,

I’ve been best friends with this person for almost 10 years, but over the past few months, I’ve started to realize something … I’m fairly sure I’m madly in love with them. I want to give this a shot, but I have no idea how to approach all these emotions I’m feeling—what should I do?

Best Friends Forever

Dear BFF,

I think everyone’s pretty accustomed to experiencing some kind of love for their best friends, especially after they carry you home from the ByWard Market after a night of too many beers—but it can be normal to feel those feelings of love too. We’re just not used to actually pursuing those emotions, so that’s probably what feels weird to you.

While that kind of “L-word” has been painted as a taboo subject for best friends to address, let alone even talk about, it doesn’t have to be.

It’s hard not to feel some kind of intimate romantic—and maybe even sexual—attraction to a person who knows you inside and out, and vice-versa. They’ve likely helped you through some of the hardest times in your life, and, on the flipside, have been by your side while you lived through some of life’s greatest moments so far. With some best friends, it can even feel like they’ve played a significant role in shaping you into the person you are today.

That being said, it’s important to take a step back here and spend some time getting in touch with these feelings you’re having, differentiating between actually loving this person as a romantic partner and loving them as a friend, which are two different things. If it does seem to be the former don’t fret: As I’ve said, these feelings are expected and normal.

I’ll be straight up about the fact that falling in love with one of your best friends is one of the trickiest predicaments you can find yourself in. On one hand, these feelings you’re having probably feel stronger than any attraction you’ve felt before thanks to the bond you already share with this person. You’re probably holding back like hell to keep yourself from telling them how you feel.

But on the other hand, there’s always the chance that your best friend won’t feel the same way—and that can hurt more than any other heartbreak. I’ll be blunt about the fact that, for some, finding yourself in this predicament can lead to the strongest of friendships imploding in on themselves.

At this point, I’d recommend weighing your options seriously. Have you ever caught the nuanced feeling that they might be feeling this kind of love too? If so, it’s worth the shot. But, if they’ve talked to you about other people they’re interested in, or treat the love as much more platonic in practice, then maybe not—this is your call and not mine to make.

What I can confidently say is if this person really is your best friend and does care about you as much as you do them, the reveal that they don’t feel the same about you shouldn’t have an impact on your friendship at its core. That’s the beauty of the most unwavering of friendships: Rather than crippling and collapsing when struck with an unexpected blow of conflict or drama, they actually get stronger. Being honest with them will do nothing but tighten your bond in my mind.

Bottom line is, I’d say that you should go for it. You’ve been best pals for almost 10 years, so even if they aren’t open to loving you in that romantic way you’re hoping for, I’m almost certain they’ll continue to love you in the friendly way they always have—even more so than before.

Love,

Ty