How do I tell my best friend that I like her?

Illustration: Nadia Snopek

@AskPeaches: I’ve been good friends with a girlfriend of mine for a little over three years. I’m lesbian and she’s been with women. She and I met through a mutual friend at a birthday party in Brooklyn. We hit it off just as friends, and both of us were seeing other people at the time. She had a boyfriend, and I had a girlfriend. But I’ve had a crush on her for all these years, and now that we’re both single I feel like it’s time to share it. I don’t know, maybe it’s the isolation due to the pandemic. She wouldn’t be expecting it, though, because we are such good friends. How do I tell her I like her?

@Sasha: Take a hint from Julia Roberts’ character, Julianne Potter, in My Best Friend’s Wedding. In a pivotal scene, while cruising down the Chicago River, Julianne struggles to find the courage to express her love to her best friend, Michael, in their last time alone before he marries his fiancée, Kimmy:

Michael O’Neal: Kimmy says if you love someone you say it, you say it right then, out loud. Otherwise, the moment just…

Julianne Potter: Passes you by.

Michael O’Neal: Passes you by. Yeah.

The look on Julianne’s face in this moment, as they go under an overpass, should be a meme for what dejection looks like. Don’t let this be you. Don’t let your moment pass you by.

My hope is that you’re not already in the “friend zone.” It can be very hard to get a friend to see you in a romantic light, if they’ve only ever shared platonic feelings for you. And the fear of rejection or of destabilizing the friendship with the news can be crippling. But I think it’s worth the shot if you feel strongly about your friend, or if you feel that she may be open to the idea. Consider as clues her past reactions or body language whenever you expressed interest in others or having to spend time away from her.

However, the way you phrase that she’s “been with women,” isn’t exactly reassuring to me that she will entertain your affections. It sounds questionably hopeful. One thing to note, as a cohort, in matters of love, bisexuals are faced with such a great degree of scrutiny, stress, biphobia, even among gay and lesbians, that the statistic are not exactly encouraging with 84% of bisexuals ultimately choosing a partner of the opposite sex. This doesn’t mean that she couldn’t be in the 9% of bisexuals who choose a partner of the same sex but understand that it may not work based solely on the numbers.

Be brave, find the right opportunity and express your feelings directly and honestly. I would suggest not having this kind of conversation over FaceTime or Zoom. Maybe plan an outing where you can be socially distanced and outside, if you’re not already in each other’s social distance bubble. Assure her either way that you cherish the relationship, however potentially awkward the situation might be. You’ve spent three years together at one another’s sides. But be prepared if her response isn’t positive and you eventually find that you’re alone in this.

I won’t spoil what happens at the end of My Best Friend’s Wedding, but it underscores why it’s important to always give yourself a fighting chance. Like the wise 60 Minutes columnist and beloved curmudgeon, Andy Rooney, once said, “I’ve learned that opportunities are never lost; someone will take the ones you miss.” You don’t have to lose yours.

In the meantime, I’ll be channeling my inner Diana King and say a little prayer for you that it all works out.

The @AskPeacheas column is prepared by committee but written from one person’s experience. Send emails to askpeaches [at] freshfruitinc [dot] com with “@AskPeaches” in the subject line. Be sure to give enough background, so the advice can be more specific and relevant.

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