Should I Date One Of My Best Friends?

How’s your love life? What questions do you have about it? Send your letter to [email protected] or fill out this form.


Hi Meredith,

I met one of my best friends three years ago, and she has become a major fixture in my life. We’ve both supported each other through some of the hardest times in our lives, including quarantine. We text or see each other nearly every day. For more than a year I have felt my feelings grow for her as more than a friend, and she has given me some hints she feels the same way. Two weeks ago, while we were chatting about our days, she said that she noticed that I had called her pretty over text a lot lately and wanted to know whether I had feelings for her. I didn’t know to respond so I asked if I could have more time.

I’m a student and an actress so a lot of my free time is filled, and I know that in the past she has asked for a lot of time and commitment, even from short-time flings (and that is how a lot of her breakups happened). I talked to our mutual friends about it during a socially distanced hangout last Saturday, and they agreed that if I like her, the good times would be really good … but the bad times would be really bad. They reassured me that they would remain both our friends even if the bad times did happen. They warned me that I was also right about her occasionally becoming becomes possessive and anxious when she’s not responded to immediately – something that I have trouble doing since I prefer being in person.

I really really like her, maybe even love her, but I’m worried that I could never meet her expectations. Am I just being commitment-phobic ? Should I try to change my life and myself to make the time for her that I know that she deserves and I want to give her? Also… we’ve been good friends for so long (with minor subtext but no almost-kisses or anything). The transition into dating feels so weird, especially during the pandemic when we both are still waiting for our second vaccines. How do we bridge the gap between friends and friends who kiss? Do friends-to-lovers ever work out?

– Outed-from-the-friend-zone


The nice thing about your very strong friendship is that you can be honest with her. You can say, “I do have feelings for you – strong ones – but I want to make sure I can give you what you need. How would it feel to be with someone with my schedule?”

You can tell her how you like to communicate between in-person visits. You’ve already proven you can talk about difficult things. Why wouldn’t you treat this conversation like anything else and call on her for support?

For all you know, she’d be very different in her relationship with you. There might be more confidence and understanding because she knows the people in your life, how you organize your day, and why you might not be responding to her text.

I wouldn’t talk to your friends about this again until you talk to her. There’s this vibe that you’re getting something like letters of recommendation about her, that you’re vetting her. Please remember that she needs to consider this, too. Make this decision with her instead of with the people you share. It’s not a democracy.

Also, be quick about this. She asked if you had feelings for her, and you asked for more time. But .. you know you have feelings for her. So tell her that, at the very least. Don’t make her wait on that kind of simple validation. Use that best friendship to tell her, “Clearly, yes, I have feelings. I But I don’t know what to do about them. Can we figure it out together?”

– Meredith

Readers? Next steps?

Love Letters

What’s your love and relationship problem?

Ask Meredith at Love Letters. Yes, it’s anonymous.

About Love Letters