Ask A Guy: How To Tell If Your Friendship With A Guy Is Too Intense

Hey Joel,

My best friend is a guy. We are close and he tells me everything. Sometimes we will talk all night. I know his secrets and he knows mine.  A few years ago he told me he used to have feelings for me but we never really talked about it, because I friendzoned him before I knew. I’ve been realizing lately that we kind of act like a couple. Even though we talk about relationships, I know something’s there, but I also know being together would be a VERY bad idea. I actually keep a list to remind myself.  I know if we dated I would love him and hate him. We would break up and be hurt. But I don’t know if he’s a mistake I have to make. (And vice versa.)

He’s about to start dating someone he “doesn’t really like” or “want to be with” but she wants a long term relationship. He doesn’t. Regardless, I know if he has a girlfriend our relationship might change, in fact I know it will because I think I act like his girlfriend. 

 So, two questions: someday, should we date even if we know we’ll break each other’s hearts? And, if he dates this girl, should he and I really talk all night and have deep conversations? Where does it cross from platonic to relationship bounds?


Before you can even answer the question of what to do about this guy and how your friendship might change when he’s dating someone, I think you need to decide on what you want him to be in your life. Either he’s “friend material” or he’s “boyfriend material.” It can only be one of the two, as the approach to each is completely different.

If he’s NOT boyfriend material, then you need to move past the “what ifs” and be okay with him dating other girls–and meeting/hanging out with those other girls. It sounds like you have a very solid friendship, so I’d think twice before crossing that line into “more than friends.” Once you cross that line, you’ll never get back to what you have now.

It sounds like you know him well enough to strongly believe it wouldn’t work out in the end. It might be an amazing, passionate few weeks or months at the start, but it would likely end in tears and frustration. If you “know we’ll break each other’s hearts,” then why are you even considering it in the first place? Friends who cross over into an intimate relationship do so because they truly believe it will go well in the end. It sounds like you’ve got too many reservations and hesitations for things to have a fair shot, so I probably wouldn’t risk it.

In terms of how to act when he is dating someone else, that’s largely up to him and his potential girlfriend. If she sees you as a threat, it could become a big problem. However, if you keep things completely platonic and that’s obvious to all, it shouldn’t be an issue. I’ve had both situations with my long-time best friend, as an ex was very much intimidated and uncomfortable with her and our relationship. In the end, I felt the friendship was more important than the girlfriend and I was very much right in my choice.

Decide whether you really want to move things to another level with this guy, and if not, find yourself someone else to focus those feelings on.

Best wishes,


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

Are you confused about a guy? Do you find yourself wondering, “What is he thinking?” Tell us everything in the comments! And if you have a question for Joel, email him at!

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