Rules dating your best friends brother
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.
In the past, I have two so called best friends *dumped* me because of my brothers.
I didn't want to introduce them to my brothers because the whole concept sounded so weird to me.
So if your best friend has a level head on his shoulder, it is perhaps okay to date his sister.
As a matter of fact, I just didn't want conflicts, my brothers didn't even know these girls exist!
Also, if she is not interested in you, you would be amazed at how much relief this can bring.
I once had a thing for one of my little sister's best friends.
(If you are new here, tune in to what she says often, because she usually is right, BTW.) This isn't just any girl. You approach carefully for the reasons you've laid out.
I would advise sitting down with your friend and having a heart to heart.