My roommate is a huge flirt and really lets guys have it when they arrive to pick me up. I’ve tried to drop hints, but she just doesn’t get it. Recently, after quizzing me about one guy, she “accidentally” ran into him. I know it was intentional because they met at a club where he hangs out. She’s never been there before and doesn’t like the music they play. She’s a great roommate in every other way and I don’t want to lose her. How can I tactfully tell her to keep her hands off my dates?

Dropping hints is like leaving crumbs on a trail under a dark moon. In order for someone to follow, they have to be on the same path and using their intuition as a flashlight. But if the initial problem is communication, it’s doubtful that they’re tracking you. What you really accomplish by dispensing occasional tidbits of displeasure is an opportunity to become very, very patient waiting for her to “get it” or very, very frustrated that she doesn’t. Either way, the problem is you, not her. You’ve chosen to communicate indirectly by presenting a sliver of your truth, rather than revealing it (and yourself) in wholeness. It’s possible that your roommate has no clue that her behavior is anything but friendly. Some women believe so deeply in a core difference between men and women that they don’t know how to just be friends with a guy. They truly have no idea that men are anything but potential boyfriends, so they can only interact sexually.

I suggest that you find a mutually agreeable time to sit down and tell her how you feel. She may accuse you of being jealous or insecure. Are you? It’s worth investigating before you talk. That way, if the accusation flies, it won’t velcro to you and you can stay conscious about the issue at hand.

By the way, remember that if you have no commitment with the guys you’re dating, they are actually fair game for someone else. Yeah, I don’t like it either. The best you can do is ask her to respect that your dates are potential boyfriends and trust that if you are meant to be with one of them, you will.

There’s a guy I really like at work. He’s intelligent, funny and aware, both culturally and spiritually, but I’m totally embarrassed to be seen with him in public because he dresses so badly. Should I tell him? I think he’s going to ask me out. A friend says I’m controlling. Am I?

It depends on how you tell him and on your attachment to the outcome of the conversation. If I had spinach stuck between my front teeth after dinner and we were headed to a party, would you point out the greenery for my sake or yours? Hopefully, for mine. If not, control is creeping in. Ask yourself: If I’m with a friend who is oddly dressed, what do I think it says about me? Write about it and see what you can teach yourself. When you have little or no concern left, you can talk to him with the vulnerability of understanding that some of the charge is related to your own history. Then you can potentially embrace him as is, if your conversation reveals that he simply disowns society’s concept of style.