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Dear Miss Information,
I am a forty-something guy in a relationship. It's been a few months, and I'm happy. But I keep browsing Craigslist's "Casual Encounters" section. I've never contacted anyone, and I don't intend to. What's behind my fascination? Is this going to lead somewhere bad? — Slave to Craig
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Dear Slave to Craig,
There are more theories here than a quantum-physics convention. They're listed below, along with degree of threat to your relationship. "1" is no threat. "5" means "recover any family heirlooms and delete all nude photos."
Theory #1 — You're a serial dater, and you've grown accustomed to combing all the dating sites. You discovered Casual Encounters while looking for an impromptu chess partner, and became addicted to reading about granny trannies and guys who clean your house naked while you smack them with a pasta fork. Now that you're in a relationship, you've abandoned all the other sites but can't seem to give this one up. Degree of Threat: 1.
Theory #2 — You've cheated on a few (okay, all) of your exes, but otherwise you're a stand-up kind of guy. You see nothing wrong with looking at a few ads, as long as you don't contact anybody. Well, nobody good looking, anyway. And how can you tell if she's good looking? The only pictures she sends you are of her tits. Besides, it's not cheating if you never meet in person. You tried, but she didn't show up. Degree of Threat: 5.
Theory #3 — You love your girlfriend, but lately, not so much. The sex is decent, but sometimes you envy your single friends. You're not unhappy enough to dump her, but you aren't exactly "in it to win it" either. You read the "Hot Slut 4 You" ads and wonder what it would be like to go out in a blaze of glory with one stupid, irreversible act. Boom! All the ambivalence is over. Degree of Threat: 3 (sober), 4.99 (drunk).
As long as you're not contacting anyone, Slave to Craig, and it's not interfering with your sex life, I don't think your Casual Encounters habit is too big a cause for concern. Looking at these ads might be harmless fun, or they may be an outlet (and a relatively safe one at that) for your negative feelings about your relationship. The only reason for you to stop would be if you were a chronic philanderer (see Theory #2) with weak impulse control. The lure is strong, and browsing this kind of site is playing with fire. If you can't stop yourself, download a program that blocks access to the site. Have your best friend set the password and you won't be able to hack your way back in. I have friends who've used this method to stop looking at the blogs/websites/Friendster profiles of ex-boyfriends and girlfriends, and it worked like a charm.
Dear Miss Information,
At the age of eighteen, I'm confident in my status as lesbian. I've been accepted to a women's college and am looking forward to some girl-on-girl action this fall. But a part of me remains hetero-curious. A few months ago, I messed around with a guy friend of mine who lives in another town. I'd like to get together and have sex the next time I see him. While I'd be up front about his role as a fuck buddy and practice safe sex, I don't want to tell him about my true orientation. Am I taking advantage of him in this circumstance? Am I compromising my sexuality? Is this a good idea? — One Night on the Other Side
Dear One Night,
In the coming year you're going to have lots of revelations about your sexuality, none of which are necessarily a fuck buddy's business. Sure, if this is someone you're going to be with for the rest of your life, you might want to tell them about your gay past, but it's not. It's a boy you screwed around with who lives two towns over.
You're fulfilling your end of the bargain by telling the guy your emotional expectations (i.e., that you have none) and protecting him from the pregnancy menace and sexually transmitted disease. Telling him you're a lesbian wouldn't be the worst idea, but I wouldn't be too shocked if he starts getting all up in your grill asking for threesomes, making dorky jokes about converting you or just being generally annoying.
I don't think this is compromising your sexuality, unless you judge sexuality by uniformity of experience. If so, then the trophy goes to Clarissa and Henry of West Peabody, Massachusetts, a WASP couple who fuck in the missionary position for precisely seven minutes every Tuesday night. If you're really unsure, you might want to put it off for a while. Maybe see how you feel after your first semester. The first semester of college is a crazy time, and your lesbo playground might give you a different perspective. Despite their reputation, most sister schools won't kick you out if you experience a little dick after you enroll.
Dear Miss Information,
My ex refuses to return the stuff I left at his apartment. It's been two weeks. The items aren't expensive, but they have sentimental value. He won't return my calls or emails. What's the best way to handle him? — Missing Something
Dear Missing Something,
In 2002 my entire record collection was thrown out by a jilted ex — everything from Thriller to my parents' Beatles and Bob Dylan. I can't say I blame him. After all, I did make out with his roommate/best friend. And even though the ex and I were broken up when it happened, I still had no excuse, so my vinyl bore the brunt of his revenge. From this, I learned an important lesson: How you act after a breakup is just as important as how you act during one.
First, ask yourself if you really, desperately need these goods. "But that stuff is mine! I own it!" All right, fine. It's yours. But is it really worth prolonging a stressful situation just so you don't have to repurchase The Big Lebowski on DVD? Funnel that emotional energy into therapy instead.
If you've determined your stuff is truly irreplaceable and you must, must ask for it back, send him a polite email that lists each item you're missing and offers different options for their safe return — drop-off at a neutral location, exchange through a friend, etc. Who knows? He may be resisting because he's freaked about you being in his house.
Whatever you do, don't use the email as an excuse to go on and on about the sentimental value attached to each item. He's sounds like he's mad and isn't going to hop on the Poor You train anytime soon. "They're special to me" is all you need to say. If you do all this and he's still resistant, have a lawyer friend draw up a letter and send it via certified mail. That usually grabs the attention. Or consider taking him to small claims court. Let me know if you meet Judge Judy. I want an autograph.
