I have feelings for friend who is very close to my best friend.

[Tidal30]

My best friend is a female and we've been best friends for years. Her second closest friend is a female that I have recently developed feelings for. We both came out relationships the beginning of the year and are single. We are both 30 and in similar spots in life, single, no kids or divorce and have similar hobbies. I have hung out with this girl with my best friends a few times in the past, and it seems at the very least, she thinks I am a nice guy and likes talking to me. Seems like on the surface there is a chance.

 

I don't know if I should approach my best friend and ask her if she could gauge the her interest or even give me any feedback/advice on this. Honestly, never have been in a situation quite like this.

 

The problem here is if I make a move and get rejected it; or we go on dates and things don't work out it could either sour my relationship with my best friend or add an air of awkwardness whenever we are all together.

 

I don't know if the risk is worth. My best friend is always talking to the both of us everyday or hanging out with us separately or together. So we are for sure her two closest friends.

 

Long time ago I had a situation where I had a close friend who played match maker with another one of his single close friends. We dated for a few months, it didn't work out, and that poor friend got caught in the cross fire for awhile (I was much younger and would never do that to a friend again).

[preraph]

It can be awkward, but it doesn't have to be THAT awkward if you are all mature, and you are. I mean, if you date her friend, don't you gossip with her about it and then if you don't work out, don't gossip with her and expect her to side with you. Just a simple "Nice, but it wasn't going anywhere" and then probably you may not be able to all hang together, but you might if you're both not real mad at each other. In other words, don't involve the friend any more than maybe asking her if she thinks her friend might be up for a date. Tell her "No, don't go ask her. I can ask her, but I figured you might know if there was any inkling of interest there and save me embarrassing myself, and also I want to be sure it wouldn't put you in any kind of awkward position." Of course, she probably will tell her friend, though, so once you've said it, it's on.

[Satu]

Engage the four powers of the Sphinx:

 

 

To Know, to Will, to Dare and to Keep Silent.

 

 

Take care.

[Tidal30]

It can be awkward, but it doesn't have to be THAT awkward if you are all mature, and you are. I mean, if you date her friend, don't you gossip with her about it and then if you don't work out, don't gossip with her and expect her to side with you. Just a simple "Nice, but it wasn't going anywhere" and then probably you may not be able to all hang together, but you might if you're both not real mad at each other. In other words, don't involve the friend any more than maybe asking her if she thinks her friend might be up for a date. Tell her "No, don't go ask her. I can ask her, but I figured you might know if there was any inkling of interest there and save me embarrassing myself, and also I want to be sure it wouldn't put you in any kind of awkward position." Of course, she probably will tell her friend, though, so once you've said it, it's on.

 

Thanks. I agree, we are all mature people and if it doesn't go anywhere, I personally feel fine with moving on in the friend triangle and not bringing it up to my best friend unless she asked about it OR acting different when I am with the two of them.

 

Do you think I should even attempt to bring it up to my best friend at all? The advantage of doing so is exactly what you said but maybe its not necessary? I know whatever happens will get back to my best friend anyway, but do you feel it looks better without asking her?

 

Here is what I am thinking today. Why not just ask the girl out for coffee or something simple and going from there? There are ways I can gauge her interest from something like that and moving forward with it from there. I don't know if she'd view asking for plans as a date/semi-date or just hanging out as friends. Honestly not too sure what is better, but I would imagine she'd agree to plans either way.

 

I should say I value my friendship with my best friend alot. I have a few best friends, but this one is the one I'd never want to lose. Too much history of helping each other out in bad situations or sharing good situations. I was an only child growing up, she's like the sister I didn't have. That kind of bond is important.

Edited August 11, 2016 by Tidal30
Had to fix a few Typos!