Should I tell my best friend I’m dating her older brother?

Me and this guy have been talking for a few weeks now. And it's getting pretty serious, but the problem is, is that he's my best friends older brother. All my other friends know about us except her. Should I tell her? Or is the whole thing wrong and I should just end it all? - Lillian F from Manhattan, NY

Oh that good old dating the older brother but are good friends with the sister situation! Here’s the deal Lilly.  Bottom line:  if you like him and you are really into him and it’s not some kind of sick game, this could be a really good thing.  Just keep in mind that this sounds like an affair.  The thrill of an affair is that it is fun.  It creates secrecy, and goes against morals/ethics/etc.  But once someone finds out, the fun of it goes away and people get hurt.  So perhaps you need to discuss with him if these feelings are real or if this is just one big mind f*** because of the rush you’re both getting by keeping it a secret from her.  If it is a rush and the secrecy is what’s keeping it going, your feelings might get hurt, but it may be able to spare her feelings and keep the friendship intact.

On the other hand should it be that he is sincere, really does want to get serious, and likes the idea of openly discussing it with his sister, it might make things even better.  One day she may become your sister-in-law.  Who knows how serious it could get?  Or the two of you can become even closer, but keep in mind that you need to set boundaries.  NO SIBLINGS EVER WANT TO HEAR DETAILS OF THEIR BRO/SIS’S LOVE LIFE.  Keep that shizzle to yourself!!!!  You won’t be able to talk about where your relationship is going or share those stupid girly details we are all guilty of. . .  you know, “Oh last night we totally messed around in a movie.”  She’s NOT going to want to hear what you and him are up to.  That and it’s not healthy.  And definitely start slow with the displays of affection in front of her.  It can come as a total shock and make her close up real fast if she’s not broken in.  Just take it slow, and come up with a strategy/game plan on how to tell her yourself.  You’re going to have to do it –  NOT HIM!!!

Remember a slow, easy approach is best.  Find a good time, like over dinner, or coffee, or whatever it is you kids do these days.  Make sure you have her full undivided attention, and be very straight forward about how you feel.  If you sugar coat it, she might not get the message.  You need to be honest, and willing to accept the fact that she might just reject the idea right after you tell her.  Be prepared for hurt feelings, and the possibility that she may no longer want to be close friends.  This is just the reality of it all.  And sometimes these situations they are worth the risk.  Just follow the advice of having the talk with the brother first, and then see how it goes from there.  Good luck!