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Should I date one of my best friends?

‘I’m worried that I could never meet her expectations’

Love Letters
Love Letters

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Q. 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 how 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 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 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?



A. 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? Would what I offer be enough?”

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. It sounds like you’re checking her references, 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?”



Pep talk, deary. It is your friend who must meet your expectations. Please don’t put yourself in a subordinate position to please people. You will be chasing situations for the rest of your life.


These are the questions you explore with her. It’s better to talk to someone you’re considering dating than to poll your friends. If she’s not capable of having a conversation like this, it’s probably best not to date her at all.


I find it strange that you needed so much intel from your friends instead of going straight to the source — your friend that you like and want to date. Why worry about the breakup before you even start dating? Try being honest with your friend and tell her you like her and want to date her, but you don’t have a ton of time, and see what she says.



You’re young enough to take a chance and live happily ever after. Or crash and burn. You’ll never know until you tell her you have feelings for her. So go ahead. Life’s too short.


“I didn’t know how to respond so I asked if I could have more time.” I think this is your answer. You seem to be doing anything and everything you can to put off deciding on what you want to do. You’re also consulting a committee of friends to help you decide if you should even try to date her. I don’t think you want to date her, but you like the idea of dating her. You should probably keep her where she is, as a good friend.


^I like this take.


^Completely agree.


Send your own relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.