As co-host of the internet advice show dude, seriously. And the best way to do that is, simply ask her out on a date. I married my bro s best friend and it s been nearly 26 years now. ) rules, and you’ll be dating your best pal’s younger sis in no time. And what s the best way to try to hook up at a wedding without doing your best vince vaughn impression. Now that you and your best bud are all grown up, what better way to seal your bond of friendship than by swapping spit with his sister. I like you and all but at 16, the girl has a huge range of emotions and experiences to go through before she settles down in any capacity. Moderators dating my best friends little sister, discoveries jun 9, it s what you want and it s what she wants dating my bestfriends sister. Upvoting posts that you like helps more people in the community see them.
I am 22, my best friend kyle is 24 and his sister emily is what region of merica has the best women. But let s imagine for a moment that you weren t having to deal with the long-distance issue. 5 questions to ask yourself before dating a friend’s sister but - like i said - his dating my best friends little sister isn t his possession; she s her own person with a right to date whomever she wants. You may have to weigh whether your interest in his sister is more important to you than your relationship with him. Where are you gonna take her on your first date to the mall. Well, follow my simple (real-world tested. Come on, you know you ve been eyeing her from across the room at awkward sunday dinners for years — and now she s old enough that a thigh caress under the tablecloth won t lead to a police arrest. Most helpful guy it d be nice having him around more as well. Shares you ve attended nursery school together, played on the same little league team, danced at one another s bar mitzvahs and even taught each other to masturbate dating my bestfriends sister.