Rupert Pupkin Redux?…Male Confusion…Female Confusion

Q: I’m a woman stand-up comic—not famous or anything, but keeping busy here in the downtown scene. I’ve got a Website that lists my gigs, and there’s this guy who comes to all—I mean all—of them. It’s better than I can say for my friends or my boyfriend, but it’s really starting to give me the willies (and ruffle my boyfriend’s feathers). The thing is, he’s never actually crossed any lines—all he does is say “Hi” or “Great job” and leave—so I feel like I can’t call him on it. Help!

A: Good one! Your instinct not to confront him, that is: It’s a good instinct. If you were to say, “I’ve noticed you at all of my gigs, and I’d like you to stop,” he might hear, “I’ve noticed you at all of my gigs!”—and think “Cool!” If your boyfriend’s feathers are so ruffled, have him come with you one night and act conspicuously boyfriendy—that alone might serve to puncture any fantasy your creepy groupie may be nurturing. While you’re at it, when was the last time you Googled yourself? It’s worth making sure no one’s erected some sort of unsavory “The Funniest and Most Beautiful Comedienne in the World” cybershrine to you. But if he goes on keeping his distance, you’re probably fine just doing the same. Though it wouldn’t hurt to add a bit about your black belt to your routine.

Q: After many happy years of bachelorhood, I started dating a wonderful woman whom I became very fond of. I did my best to turn on the romance. I bought her flowers, took her to nice restaurants, and sent her nice cards, always acting the perfect gentleman. In short, I did everything the right way. I even kept my natural urges in check—until one fateful night when, after almost six months of dating, we had wild, raunchy sex in the backseat of my car in some abandoned parking lot in Brooklyn. Ever since that night, whenever I call her, I get the royal brush-off. What gives? Did I do something wrong?

A: Sorry to have to tell you this, but after “many years of bachelorhood,” might you be a little naïve about the opposite sex? And frankly, the “wild, raunchy” scene you describe, followed by her never speaking to you again, almost sounds sorta kinda like, with all due respect, a vaguely date-rape-ish situation. Then again, it could just be that she didn’t think it was as hot as you did and decided to call it off because of a lack of chemistry, but then there’s another disturbing element: this weird line you seem to draw between your repressed “natural urges” and your big-spending–“gentleman” alter ego. Which suggests that, yes, you probably did something wrong. And if your former date isn’t talking, you might consider seeing someone to help you figure it out: a therapist.

Q: I had a great first date with a man. We are both 53. We talked, held hands, kissed … it was really good. He called me when he got home to say he made it safely and had a great time and he would talk to me later. I called him the next day and we talked a few minutes; I wanted to keep it short because I’d told him I had just called to say hi. Now it’s been five days and I haven’t heard from him. Should I give him a call? Send him an e-mail? What do you think is going on?

A: What’s going on? Perhaps he has been kidnapped and is this very minute bound and gagged but still screaming your name. So rush right over there and untie him so you can go off and get married immediately! Sorry to break this to you, but when some-one doesn’t call you for a second date, no matter how good you think it was, the most likely reasons are that he’s having a busy week (it has been only five days, after all) or—and here’s where it gets really unfathomable—he doesn’t want to go out with you again. Either way, calling him won’t do any good. The ball’s in his court.

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Rupert Pupkin Redux?…Male Confusion…Female Co [...]