My pal O is tall, good-looking, in his 40s, and a near virgin. Throughout his 20s, O was so constipatedly Catholic that he avoided dating for fear of being tempted to sin. When he finally did start dating in his mid-30s, he was hampered by both the clumsiness and awkwardness of a teenager and the notion that he ought to get someone extra wonderful after waiting so long. But God does not reward stupidity.

Recently, a clueless mutual friend put two and two together, got 17, and told this guy that I wanted to bed him (not true, although I have a weakness for inexperienced men). So O asked me out. I told him that I am in a monogamous relationship, then I did my best to put him at ease. Since then, we’ve occasionally had dinner together. Last time, I necked with him briefly out of curiosity, and to take my mind off a temporary crush on another guy. O’s got eagerness but nothing else to make up for a serious lack of chemistry.

Even if I wanted to cheat, I don’t do mercy fucks. Moreover, he’s obviously not into me personally; he’s just desperate. Teaching is fun when the guy is shy and/or inexperienced but also really into me and otherwise suits my taste. That’s not the case here. He’s a turtle on his back, and I feel sorry for him.

I think he needs teaching even worse than he needs to get his rocks off, and I’m not convinced that whores-with-a-heart-of-gold exist outside of the movies. Besides, he is too scared of disease to try a call girl. I don’t know anyone I can fix him up with. How can he best seek out a kindhearted, nonprofessional fuck buddy who’ll teach him how to please a woman, so he can get on his feet and maybe have a successful relationship thereafter?

Not Going There

Good on you for saying no to the pity fuck (the worst of all the fucks). It’s been my experience that those never end well.

I’m guessing your pal is probably in need of a lot more help than a sympathetic friend and a newspaper columnist can offer. It’s obvious that he has severe Catholic damage, which can manifest itself in many ways, none of which will be any fun for the women he’ll eventually sleep with. (“Hello Ms. Madonna, let me make you my WHORE, then I’ll treat you like shit and kick you out the door!”) I know this because I’ve dated men like him. (OK, there was only one, but damn, he left his mark.) You should definitely not fix anyone up with him. (Unless you have a slutty friend that you secretly hate.)

Hiring a pro won’t help, either. A hooker won’t teach him how to throw it, and even if he did get up the nerve to go there, the ensuing guilt just might kill him. This “kindhearted, nonprofessional fuck buddy” you yearn for exists only in your dreams. This dude needs shrinkage and a lot of it.

But the thing is, he probably won’t get it. It’s nice that you wrote a letter looking out for him, but he’s a big boy. He needs to take action if he wants to get action. He could check out the American Association of Sex Educators, Counselors, and Therapists for a referral (www.aasect.org). Or he could ask a therapized friend for a recommendation. But these are things he needs to do.

You’re missing the point of the bachelor party [Dategirl, “Fräulein Freak-out,” March 15]. We are not celebrating impending nuptials; rather, the groom is saying goodbye to bachelorhood. Those boobs in your face and naked body rubbing against you will be the last ones you see except for your wife’s (if the marriage is successful). Get it?

Helpfully yours,

Me

Oh, OK, I get it. Then, by using your reasoning, you’re saying the bride should go out just nights before the ceremony and administer as many blow jobs as she can stomach because (hopefully, if the marriage is a successful one!) she’ll never taste another man’s seed once she’s married.

Hmm. Know what? That still doesn’t make sense.

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