"Hey I am really interested in your sister but don't want things to turn awkward if it's not mutual. " Even better, have this conversation with your friend's dad.This helps you avoid potential awkward moments with your best friend and Dads are supposed to be able to have these conversations when their daughters reach adult years.Also, if she is not interested in you, you would be amazed at how much relief this can bring.

friend dating sister-89

You need to talk to your friend about this and gauge his reaction. (Or you could choose to go ahead, to hell with friendship.) But if you care what your friend thinks, you'll run it by him first even if you are 99% sure he'd be fine with it. I had a few sister of friend oppurtunities back in my late teens adn early 20s.

You might think he'd be OK with this, but if you ask her out and he's not, it's going to be awkward between the two of you. I was real close to one of them and had a few back of my mind type moments where I wondered if there could be a spark there.

Personally, I don't think it's a good move going out with a best friend sister. Personally, I don't think it's a good move going out with a best friend sister. -I see her a few times a year and we always get along and laugh. -Haven't told best friend but sure he would be fine with it.

One is risking a lot if it goes sour; especially if one is that close to the family. One is risking a lot if it goes sour; especially if one is that close to the family. Lol-Been best friends with this guy since we were toddlers. -I feel like we have a more brother sister relationship since we've known each other so long. I can't just ask her out because if it some how fails, every time I'm with there family it will be awkward as hell.

It was amazing how different things were after that.

I had closure and while I still had a slight crush on the girl, it really helped me move on. " But if he has a problem with it, then you'll know and you can decide to lay off the sister.

I finally decided that the possible loss of my friend mattered more in this case and also the oddness of moving from friend of the son to possibly dating teh daughter would feel odd for me and the parents, so I didn't go forward. For me it would depend really what I thought of my friend.

I have some amazing friends I would have zero issues dating my sister.

One day I couldn't take it anymore and asked my sister if her friend would potentially be interested in me.

What I didn't realize is that my sister had already tried to play match maker and her friend was not interested because she was too close to me like a brother.

So if your best friend has a level head on his shoulder, it is perhaps okay to date his sister.