Dear Mistress Maeve,
I've been single for a while, and I'm looking to get back into the dating game. I recently was introduced to the older sister of a close friend of mine, and we hit it off. About a week ago I had a party at my house, which both my friend and his sis attended. I found out from my friend at the party, in some vague terms, that his sister had some interest in me. He also, while hammered drunk, gave me his "full blessing" to "hit on [his] sister".
However, I worry about whether he actually feels comfortable about it. He's the kind of guy who is more apt to put on a brave face than speak out about something that bothers him. On top of that, his sister is coming off a serious relationship, and I don't know her thoughts on dating again. Personally, I'm not expecting anything serious, and it makes me worry that if I do opt to pursue the sister and it doesn't work out, things will become awkward between the three of us. Do I take a shot with the sis, or play it safe with my buddy?
Bro Code in Boston
Dear Bro Code,
Forget it. If you're "not expecting anything serious," don't even go there. The Bro Code — a set of laws dictating how dudes interact — prohibits you from pursuing a relationship with your buddy's sister unless you are ready to make her your bride. Given your lukewarm feelings and her fresh-out-of-a-relationship status, you are better off hosting your pants-off dance-off with someone else.
However, if your feelings for her grow, there is hope. Have a talk with your friend. Let him know that, while you appreciate his drunken blessings, you'd prefer his sober reassurance. If you date her, you must be the consummate gentleman — you'll have little room for error in this relationship and a high price to pay if you screw it up. Be sure you care enough about this girl to risk your friendship with your buddy — because that's exactly what's at stake.