I have a crush on this guy whom I work with. We've known each other for a couple of years, and he is kind of messed up. He drinks too much and obviously doesn't take great care of himself, but he's smart and he is a really talented musician. I seem to always be attracted to guys who seem like they need help. My friend who works with me thinks I'm crazy. She thinks he is immature and a mess and that I am just asking for trouble dating a guy like that.

Anyway, I'm really shy, and I'm worried about if it will be awkward if he says no, if I even do get the courage to ask. The thing is, he has asked me before to come to his music shows, and both times he invited me I really couldn't go because I had other stuff to do. I told him why I couldn't go and that I wanted to, but the next show he didn't ask. But I went to that show anyway, even though it was a little farther away and I had to get up early the next day. He didn't really react to seeing me there, and now I don't know what to do. I know he is still single, but I am so shy! I don't think he will ask me out again but I don't know how to ask him! Or even if I should. Does this sound like a bad boy to you? Will I just get my heart broken? Help!

First, while I agree to an extent with your friend—I have often said that you can't date potential—I also think that it's easy to miss out on potential partners by dismissing them because of how they act when they're not in a relationship. Many people would prefer a quiet dinner at home and a beer or two every night, but not having anyone to share that with means that they choose instead to go out all the time and hang out in bars drinking because they're lonely or bored. I am not saying that this is necessarily the case with your guy, but you should definitely consider the possibility. It sounds like you have already decided to ignore that bit anyway.

As for how to ask—just ask! This is a guy you have known for a while, which means he knows you're shy. So, go up and say "I've been trying to figure out how to ask you out for months now—so how about it? Do you want to get dinner sometime?" The more you make a big deal out of this, the more difficult it's going to be to do it. Just ask him already!

I just found out that my younger brother is gay. I'm in my early 20s, and he is 19 and still living at home. I'm slightly pissed that he didn't come out to me (I found out by accident when I came home from school and ran across his porn stash in our shared bedroom) because we have always been close and I feel like he should have felt comfortable telling me. I have always stuck up for him our whole lives. I don't understand why he would hide it from me.

Anyway, when I confronted him he didn't try to deny it or anything, and I kind of yelled at him for hiding it from me. Then, a few days later, I saw an interaction between him and one of the neighbors that was kind of odd. It took me a little while, but I finally put two and two together and figured out that they are obviously hooking up. The thing is, this guy is married and has kids. I confronted my brother about it later, told him it was wrong and that he should find somebody his own age, etc. I told him the guy was using him and he's going to get hurt, and think of his wife and kids, etc. He said the guy's wife knows, that the guy is bi, and the wife doesn't really care. The kids are too young to know anything, too, so he's not hurting them.

I still don't like this, and I don't know what to do. I am afraid if my parents find out that my dad will kill this guy. I don't think my parents will care too much that my brother is gay, even though I am sure they would prefer that he wasn't, but an affair with a married adult? That's too much. On the other hand, my brother is a big boy and he can take care of himself, and it's not really my parents' business. What should I do?

Big Brother

There's not a whole lot you can do, BB. As you said, your brother is an adult. And if this guy's wife does know (I'd be lying if I said I wasn't skeptical about that, by the way, but you don't seem to doubt it so I'm rolling with it), and she doesn't mind, then it's really nobody else's business. Open relationships can work. This is a situation you can't protect your brother from, BB, no matter how badly you may want to. Just tell him to be careful and that he can come to you if he needs anything, and then walk away and hope for the best. And, hey, maybe you can introduce him to some gay guys his own age if he comes to visit you at school.

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