Q: This question comes from a point of real frustration. I'm a 26-year-old straight guy. Due to my being overweight, awkward and generally unable to attract women I'm actually interested in, I have only been sexually intimate with prostitutes and women of low caliber. I have never been able to sustain an erection during intercourse. I've climaxed during oral sex or hand jobs. I'm not physically accustomed to getting off with anything but my hand. Worst of all, the intense fear of impotence has caused me to avoid sexual liaisons. When dating, I feel threatened by the expectation of sex within the first few dates. Any solid advice? —Sick Of Beatin'
A: Join a gym and lose some weight. You'll gain some confidence and improve your health — and your circulation — which could help in the keeping-the-dick-hard department. (I'm not telling you that you have to transform yourself into a muscle god to be happy or find love.) Seeing a doctor and getting your hands on some Viagra couldn't hurt, either. Vary your masturbatory technique.
Stop sleeping with women unless you're attracted to them on some level, and recognize that holding the women who will sleep with you in contempt is an expression of self-hatred and knock it the fuck off. Since sex within the first few dates makes you feel anxious, inform anyone you date that you're not up for having sex within the first few dates. And the next time you find yourself in bed with someone or sense that things are headed there, SOB, tell her that you're really only interested in oral and mutual masturbation — at least at first — and that you generally take a long time to come. Then you don't have to stress out about failing to meet her expectations, because she won't be expecting anything other than what you're capable of delivering.
Finally, there are sex workers out there who will not only get you off in exchange for your money, SOB, but will work with you on improving your skills and building up your confidence. You may have slept with one already without realizing it because you so resented having to pay for it that you dismissed her as a cheap whore to protect your ego. Dumb mistake.
Q: I'm a heterosexual male. I've never been in a long-term relationship, I've never been in a short-term relationship, I've never been in a relationship. Four make-out sessions in my youth and paid sex with cheap street prostitutes is all the physical intimacy I've ever known. And sometime before the end of this year, I'll be turning 45. I have no explanation for how I fucked up something this important this badly for this long, but here are my best clues:
1) Deep down, I don't think I've ever really believed women could possibly find me attractive.
2) For me, being rejected or humiliated after approaching someone is an almost paralyzing fear.
3) My professional, career and financial situations are only slightly better than my romantic and sexual situations: I'm always either barely getting by or in some crisis where staying non-homeless is my only priority.
I want to understand what the fuck is wrong with me and why I'm staring at a lifetime of totally unfulfilled romantic and sexual hopes and dreams. The last thing I need right now is some Pollyanna bullshit. I want brutal honesty. —A Lifelong Onanist Needs Explanations
A: Some people are alone all their lives because they're too damaged or too terrified or too terrifying, ALONE, and some people are alone all their lives because they are simply, as the cliché goes, unlucky in love. It sounds like you suffer from social and sexual anxieties — damaged and terrified — and could benefit from seeing a shrink. You say you're barely getting by, ALONE, but if you're spending money on cigarettes or booze or pot or all three, well, you might want to prioritize your mental health over those nonessentials.
Now here's the usual line of Pollyanna crap that we advice professionals are supposed to squirt out for people like you: There's someone out there for everyone, kiddo, hang in there! But that's a lie, ALONE, and you know it and I know it and everyone who's ever said that knows it. If it were true, then … no one would be alone all his life. Unfortunately, I can't just tell you to accept that you're going to be alone all your life because we can't know for sure that you were one of those people — one of those people destined to be alone all his life — until your life ends. So here's what you need to do between now and death: Keep a roof over your head, put food on your table, get some help with your emotional problems, and take your pleasures where you can. Do things you enjoy — alone, if you must — and you might meet someone along the way.
And finally, ALONE, if the only intimacy available to you is paid sex with cheap street prostitutes — or, as they prefer to be called, "conveniently located and economically priced sex workers" — that's better than nothing. Remember: Sex workers are part of the solution for you, if not an entirely satisfactory solution, so have a little gratitude and treat them with respect.
Q: I'm a 60-year-old white male, securely retired from a successful professional career. I own a nice home that's paid for. I ought to be happy, right? There's just one catch: I'm still a virgin.
Growing up, I suffered the outcast status to which class brains are routinely assigned. So I fell behind socially. Then I went to an elite, all-male university and fell even further behind. The sexual revolution passed me by. So I retreated into my career. I never learned how to date. I considered paying for sex, but I decided that was the equivalent of admitting that I was a failed human being. Now I spend my days consumed with loneliness, resentment of the past, and a constant longing for a hint of intimacy. Longevity is a family trait, and I expect to live into my 90s. Is there any plausible way to salvage something from this mess? —Stop The Parade, I Want To Get On
A: You've got a big advantage over ALONE, STPIWTGO, in that you're financially secure. That's something that many women look for in men — women are sex objects, men are success objects, blah blah blah — and you could leverage your professional success to your personal advantage. You wouldn't be the first man who was paying for sex but, since he was careful to launder the money through a relationship, wouldn't have to admit to "paying for sex." So, STPIWTGO, why not sell the house, move to a retirement community where single women outnumber the men, wear nice clothes, and drive a nice car?
But first: See a doctor. Reading your letter, I wondered if you don't suffer from an undiagnosed case of mild-to-moderate autism. There's no cure, but a diagnosis might make you feel like less of a failure, STPIWTGO, and it could give you a better idea of the obstacles you need to overcome to make a personal and romantic connection with a woman between now and death. And I know you're opposed to "paying for it" in the traditional sense — no conveniently located and economically priced sex workers for you — but you also might want to consider seeing a shrink who can refer you to a sexual surrogate. Then your insurer will pay for it, STPIWTGO, not you.Download the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage. Send letters to firstname.lastname@example.org