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Dear Dan —

My brother is 22 years old and mentally ill with social anxiety on the scale of agoraphobia (officially diagnosed). He's made significant progress in the past few years, but he's stuck on the fact that he's a virgin and is convinced that he's not going to make any real social progress until that's no longer a fact. His particular problem makes it impossible to reason with him—he's a little Asperger's-y—and he is convinced that he will only be able to pursue a job, have a social life, and tackle other obstacles after he loses his virginity. Financially, it would be easy for me to drive him to Nevada and eliminate the virginity issue. He's asked our mom to do so. My family isn't hung up on "purity" where sex and virginity are concerned, so we're open to this. I don't have any illusions that this will solve his problems, but my mom and I are hopeful that it would eliminate an excuse that's keeping him from taking positive steps forward. Should I offer to take him? Or force him to sort it out on his own despite his crippling social issues?

— Socially Interactive Sister

"I want to commend SIS for considering the services of a sex worker in such a positive and nonjudgmental way," said Siouxsie Q, a San Francisco–based sex worker and the creator and host of The WhoreCast, a weekly podcast that seeks to humanize people working in the sex industry. "And I want to reassure her that the right provider is out there for her brother."

Some will object to your hiring a sex worker to help your brother out, of course, but you can tell those people to go fuck themselves—or you can tell them to rent The Sessions. In that acclaimed 2012 film, John Hawkes played a poet who is paralyzed from the neck down. Helen Hunt played a sexual surrogate—a clinical/glorified sex worker—that the poet, with the blessing of his priest, hires to take his virginity. No one had a problem with the sex-work aspect of The Sessions because Hawkes's character is so profoundly and obviously disabled that audiences sympathized with his plight: It would be difficult, if not impossible, for him to get laid any other way.

So hire a sex worker for your brother, SIS, if you think it will help—even if it just eliminates an excuse that's blocking his progress—and there's no need to drive to Nevada. Siouxsie suggests you look for an "experienced" (read: somewhat older) escort with an online presence in your area. So what do you do once you locate a prospective sex worker in you area?

"Send an e-mail explaining the situation and your brother's special needs," said Siouxsie. "There are sex workers out there who specialize in working with clients with disabilities, and many have experience working with clients who might be very similar to her brother."

Once you find your local Helen Hunt, SIS, prep your brother for the experience. "Give him a pep talk," said Siouxsie. "Let him know about etiquette and protocol: no haggling, no prying for personal information, his personal hygiene needs to be impeccable, and he should know the basics on protection and STI transmission. Above all, he needs to treat her with respect."

I'm a straight guy who recently got out of a long-term relationship. Best sex of my life: Physically, she rocked my world. Unfortunately, she rocked my world mentally, too. I finally feel ready to date again, and last week I met this drop-dead gorgeous girl. Intelligent, successful, positive—an unbelievable catch. She even pursued me! But there is just one thing, and it's killing me: She is a skinny girl. In the past, I've always dated women with curves. This girl is gorgeous and athletic but she's also skinny. Am I objectifying women's bodies here? Am I fetishizing curvy girls too much? What is my dick thinking here?

— My Dick, My Annoyance

The dick wants what it wants.

That said, MDMA, sometimes the dick wants more than the guy attached to it realizes. You may discover, once you start fucking around with this girl, that your dick must have curves and this girl is just too skinny for you. Or you may discover, as so many men have discovered before you, that your dick wants more than one narrow type. Sometimes it takes meeting someone wonderful who isn't the ideal you've locked onto to realize that your dick was into more than one thing, but your brain—your bigger and more powerful sex organ—was shutting your dick down.

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