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Pursuing a relationship with close friend whose brothers are also close friends.


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I am interested in starting a relationship with one of my close female friends (I am a 26 year old man). I sense that we have a mutual attraction to one another and she probably already knows I like her. When we go out as a group, her and I sometimes flirt when nobody is paying attention. There are a few obstacles that have made it difficult to let her know how I feel. First, I am very close friends with her already. Second, I am very close friends with her two brothers, as well as her parents. Because of this, the situation is very delicate and I am not sure how to go about this. I have written a letter to her that I am considering sending her. Please let me know if you think I am approaching this in the right way. Here is the letter:


Dear ****,


Life is weird. I really don’t want you to feel uncomfortable, but what I am about to tell you might make life a little weirder. I feel like I need to be honest, even if it is hard to process. Maybe you already suspected this, but I have liked you for some time now (in an emotional/romantic/sexual way) and I wonder if there is possibility of a future for us in that capacity. In other words, I fink u freaky and I like you a lot! Haha! I haven’t done anything about this because I’ve had the impression that you were “off limits” (not sure if this is true or not) and I was worried about overstepping boundaries. I just needed to get this off my chest so I can move on. I would have rather talked to you about this in person, but we never have much privacy when we’re together.


If you feel the same way:

Yeah! We can move forward however we want and be awesome. This may include some awkward moments for us and your family to deal with, but I can handle that if I need to.


If you don’t feel the same way:

I will not hold it against you in ANY way. I will continue to love you as a friend. I love hanging out with you and our friendship is very important to me. I really hope that this won’t change your mind about that. You deserve to be happy whether it is with me or not. You’re a great girl and any guy would be lucky to be with you.


I know you are probably thinking this is weird. I agree that it is a little weird, but I don’t know what else to do. I hope this doesn’t creep you out or make you not want to be around me. That would suck really bad! It is really important that you understand that I am not trying to pressure you into anything. ABSOLUTELY NO expectations or time constraints are on the table, just my honest feelings. Please don’t think of me as a jerk for putting all this on you now. I’m taking a big risk here and it is not easy for me. I wouldn’t be doing this if I had not thought about it for a while. I am sure about the way I feel.




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I dunno. There's nothing wrong about your letter but it seems that sending it might send a wimpy, beta-male vibe. Plus it's SO concerned with not offending her, it's almost as if you're scared to actually admit your feelings. That's high school mentality, not adult and not very confident. If she's attracted to you, this note might even turn her off.


Why not ask her out on a proper date - dinner and a movie, then go in for a kiss at the end? If she reciprocates, yahtzee!


And if she doesn't, I hardly think she'll consider you a horrible person for trying, and will probably give you points for being confident enough to go for it without hesitation. Just accept her rejection and at that point you can just tell her IN PERSON the stuff you wrote above. Then lick your wounds at home for a week, then never mention it again when you see her. Done.


That's my vote anyway.

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