Kiss and Tell?

Dear Mistress,

I have a friend who is good friends with her ex-boyfriend — let’s call him “Jack.” I hang out with my friend and Jack from time to time, and we get along well. Luckily for me, when Jack and I get a little drunk, we tend to have make-out sessions. My friend has not shared with me whether or not she is bothered by the kissing, nor have I asked her. Kissing is as far as it has gone, but I kind of like him. Since he and I have done this multiple times, I am wondering if he likes me, but I don’t have the guts to ask.

Is it appropriate to have drunken make-out sessions with your friend’s ex? We’re adults, and we’re having a good time. I sense my friend is protective of Jack, so I haven’t asked him for more than kissing —I think it would be uncomfortable talking with her about it. I would rather remain friends with her than start something with him and ruin our friendship permanently. Do I just suck it up and tell her that I like him? Tell him? Help!

Miss Kissdon’tell

Dear Miss Kissdon’tell,

You’re all over the map. In one breath you say that you like “Jack,” yet in the next you’re ready to ditch him in order to preserve a friendship you’ve already put in jeopardy. In most instances kissing is relatively harmless, but in your case, you’re risking a friendship for some drunken thrills. It’s time for you to decide what you really want, and then take action. If you really like this guy, sit down with your friend and tell her about your feelings. You don’t have to ask her permission to date him, but talking with her first might prevent tension down the road. Hopefully your candor will soften her protectiveness, and she’ll give you her blessing. If she protests, you’ll have some serious thinking to do about what’s more important to you.

On the other hand, if you’re not head over heels for this guy, stop kissing him. Why risk a friendship for someone who doesn’t really interest you? And while you’re at it, ask yourself why you’re inviting so much drama into your life. Take it from me: Drunken kissing trysts are much more fun when drama is not involved.

Martini Kisses,
MM