originally published January 10, 2007

I have been dating this guy (whom I will call Matt) long distance for a couple of years. We both have good jobs and have never talked about either of us moving, but I have been planning on moving to the city he lives in sometime in the next year and have been looking for a job there. We have never really discussed exclusivity, but I can usually tell if he has something else going on by the frequency of his calls and visits. Recently, I met and started to date another guy, and I didn’t tell Matt about him because I wasn’t sure where it was going to go. Well, things started to get more serious with the new guy, so I decided to tell Matt about him. I tried to call him a couple of times, and he didn’t call back, which isn’t unusual because he travels a lot for work and we often go for a month without talking on the phone. I was particularly anxious to get the conversation over with, so as not to have any guilt while pursuing my new relationship, so after trying unsuccessfully to reach Matt for a few days, I wrote him a 15-page letter explaining how I felt about him, about us, and about trying this new thing out before making any final decisions about my moving there. I sent the letter, and feeling that I had done what I needed to do to be fair to him, I went out with the new guy. Actually, I went out with the new guy several times, and we slept together, and things seemed to be going well. I never heard back from Matt, but I assumed that he had gotten the letter. After about a month, the new guy wasn’t working out as well as I had thought. He stopped calling as much, and I realized that he wasn’t that great for me, after all. So I tried calling Matt again, but I didn’t get an answer. I have now called several times, sent emails, and written a letter, trying to be lighthearted and even naughty, and he won’t call me back. Do you think it’s fair for him to be jealous, considering that we never discussed exclusivity and that he has seen other people? I thought I did a good job of explaining everything in my letter to him and if he had a problem with it, he should have called me right away and told me he didn’t want me to see anyone else, right? I really, really like him (I might be in love) but I don’t know how hard I should fight to keep things together between us because I don’t think it’s fair for him to hold me to a different standard. I’m 28 years old (he’s 30) and I thought we were old enough to be realistic about the circumstances we’re in. Now I don’t know what to do. Help!

You’ve Got Mail

Let me get this straight, my postal princess: You wrote a 15-page letter to a 30-year-old man that you are barely dating, ostensibly in order to let him down easy about a guy you are about to start sleeping with, meanwhile detailing your previously unmentioned intention of moving to the city where he lives and pouring out your feelings for him, and you think he’s not calling you back because he’s jealous?! Do you have any idea how crazy you sound? What could you possibly say to the guy that would take 15 pages? I would guess that he’s avoiding you because you freaked him out. Leave the poor guy alone, find somebody to date locally, and - for the love of god - slow down.

There is a girl, a woman, I should say, that I have been admiring for a long time. I used to see her at the coffee shop where I worked at least twice a week and we would small talk, and then it got to where I would take a smoke break when she came in. We never said anything that big or important, but we did have a routine and I know she at least liked me as a friend. She usually hung out for about 20 minutes and then she would rush out “to work.” This went on for about six months, twice a week, almost like clockwork. For about five of those six months, I had a girlfriend, so I didn’t think anything of it. I thought she was cute, but never thought more about it than that, really. Eventually I got another job, and I didn’t see her unless I went back to the coffee shop, which wasn’t convenient for me. I never got the guts to ask her out, but one day I did follow her. It’s not as creepy as it sounds, because I was going the same way anyway, but I wanted to see where she worked. Now, I know this is going to sound ridiculous, but I was too embarrassed to ask any of my friends. Has anyone you know ever had a successful relationship with a stripper? She seems really cool, but I just don’t see how anyone could do that job and stay normal.

Curious George

No one that I know personally has ever had a relationship with a stripper that worked out, CG, but that doesn’t mean it’s impossible. The first thing that jumped out at me about this letter, though, is that you said you were “too embarrassed” to mention this girl and her line of work to your friends. Think about that before you bother asking her out.

What you really ought to do is talk to her more. You never even bothered to ask her out. I guess when you worked at the coffee shop it would have seemed silly to ask her to out for coffee, but now that you don’t work there, and you know she likes coffee…

The only way for you to find out how normal she might be is to get to know her. She may be a total nutbag, or she may be a perfectly cool chick who happens to take her clothes off for money. Whatever you do, don’t go and try to talk to her at work, or stalk her there, or expect to see who she really is onstage (assuming she actually is a stripper and not a bartender at a strip club - have you considered that possibility?). In fact, don’t go there at all unless she invites you.

Jyl Inov

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