Essentially the title, but more details here. I’ll name the friend that likes me Michael & the person I’m with Jack for clarity, though names are obviously fake.

I’ve been friends with Jack for 4 years. We weren’t that close but would meet up / play games throughout the years. Last year, he introduced me to Michael and we became close friends in the last few months. Michael is one of the kindest people I know, he’s helped me through a lot. It became really obvious the last few months that he likes me (says he misses me, calls me cute, etc.) though he hasn’t said anything.

Jack & I recently found out we’re more compatible than we thought and are currently discussing the potential of dating. Main thing holding us back is distance. Jack & Michael go to the same uni, which is how they met, and they’re decent friends.

My question is – how do I tell Michael I’m with Jack, if we decide to date? I think Michael would be crushed – he’s told me it takes a long time for him to get over people, and has said before that he would be sad if I dated somebody else. He’s genuinely one of the kindest people I know. What’s the best approach? What can I say? Should I offhandedly mention that Jack and I are together, given that Michael hasn’t said anything? Or should I address his feelings when I tell him? Pretty sure no matter what, our friendship has to take a break.

As a side note, I’m worried about Michael comparing himself to Jack later on too. Any way to mitigate this?

Thank you

2 comments
  1. Idk man, if he was that kind he wouldn’t be saying how sad he’d be if you were dating someone else, that’s kinda shitty thing to say to someone. It doesn’t mean he’s a shit person, just lacking some tact that it’s not just his feelings that matters.

    You and Jack do your thing! Don’t let Mike (imma just say mike lol) be an obstacle. You don’t necessarily need a formal conversation with him because he’s never confessed, you and mike have never had any situationship. If anything, you and Jack can post a photo together with heart eyes or something like that. It makes it clear you two are on a date and dating without being like “hey mike I know you’ve liked me for awhile but I’m dating someone”. It’s a bit much to make this a formal conversation about his feelings because that’s just to spare his feelings and weirder because he’s never confessed. In this case, it’s best to pretend and be dumb about his actions and post a picture of you and jack on a date or even hit mike up with a “omg, Jack and I are finally going on a date. I’m excited” type of friend-text.

    Whatever route you choose, Mike will feel crushed anyways. But you can’t control how Mike feels. He will have to move on himself. It sucks he likes you while you and Jack like each other but it is what it is. It will likely negatively effect both your friendship with him for awhile.

  2. You should let him know and if you’re his real friend encourage him to meet other girls and introduce him to some of your friends.

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