Lucinda, 27

How do I tell a potential hookup that I have bedbugs?
You can tell after a few dates whether the person will judge you for it or be cool. The second time ours flared up, my two roommates knew and they didn’t tell me. Unfortunately, I didn’t tell my new boyfriend because I thought they had been gone for three months. So the second or third time he stayed over, he woke up with the telltale red dots on his arm. He was visiting from out of town, so we had to wash all of his clothes at a laundromat. It was really embarrassing. But it worked out; we’re getting married.

Is there a sexy or funny way to ask someone if they have bedbugs?
No. But a non-sexy/funny way, if you want to be creepy about it, is checking their address on the bedbug registry website.

My best friend went through a really bad breakup a few months ago. She's spent the past three weeks communicating with a man online. They haven't even met up yet, but she's already way too into him. How can I tell her to calm down without sounding judgmental?
Don’t be the asshole friend who says, “Well, maybe he’s not going to like you.” It would be one thing if you met the guy and knew it was a bad situation, but who are you to tell people what to be excited about?

What should I include and what should I leave out of an internet personal ad?
People take what they put in their profiles too seriously. It’s never a good idea to misrepresent yourself but, don’t put everything out there, either. On the other hand, I’ve seen a lot of people whose pictures are all of themselves taking their own picture. And they have to think of what message that’s sending. You don’t have one friend who will take a picture of you? So step back and think of little things like that. Maybe you do have a friend, and you just didn’t really think of how that would come off.

I had one awkward hookup with a woman I've known for years, and the sex was terrible. Despite our off-night, I'm still really attracted to her, and want to give it another go. When I approach her about a rematch, is it best to acknowledge the previous time was bad?
If you got to that point and there’s not enough chemistry to take you forward, that’s a sign. You either have that chemistry with that person or you don’t.

A buddy of mine is seeing a woman who thinks they're exclusive. She was recently gushing to me at a bar about how lucky she feels to have a "boyfriend" like him. I told him that he needs to tell her he's still dating other people. He disagreed. Should I say something to her?
I’ve heard people say things like, “Oh, the bro-code. Don’t ever fuck with someone else’s whatever.” I wouldn’t go to the girl, unless I knew her very well. But I would certainly reiterate to my friend that it’s pretty clear the girl has high expectations and he’s probably going to hurt her. Tell him to man up.