Dear Sasha,

I’m a 43-year-old, socially shy, inept, never-dated, no-girlfriend-ever, never-had-sex, living-at-home-with-Mom guy. Should I kill myself?

Not a solution, I know, but an ending, definitely. Tired of being a virgin, tired of my inability to “get into the game,” tired of psychiatrists, psychologists, counsellors, therapists, tired of generic advice and suggestions, tired of trying to feel good about myself, tired of being a joke.

The Reluctant Virgin

You are not a joke. You are one of millions of people struggling with love and intimacy to a radical degree. The biggest problem for those facing this challenge is the dearth of positive, common-sense information about involuntary celibacy.

How do we calmly and non-judgmentally integrate people wrestling with their sexual identities in such a fundamental way into the broader sexual culture? The degree of shame attached to this is completely out of proportion and leads to secrecy and humiliating roadblocks.

We have education systems in place for adults to catch up on many important social cues and milestones, so where the hell are our adult sex ed classes? It seems the only “educators” visible in this field are attempting to profit from your shame by attaching anger to it, suggesting you cultivate some mysterious “killer instinct,” as though you’d been deliberately deprived of sex and now must treat prospective mates as quarry rather than a partners.

I say this with great confidence, Virgin: you can change your life, but you must be willing to take it in hand by integrating yourself into a sex culture that is affirmative and well-informed and by having a vested interest in your health and pleasure and that of your partners.

Many sex shops have a variety of workshops. Why not suggest to your local ones that they try some basic adult sex ed? It’s difficult to connect with sex surrogates in this country, but go to the Board of Examiners in Sex Therapy and Counselling in Ontario ( and see if you can’t talk to a shrink who may have one on his or her roster. Many sex workers are also great with first-timers. Peruse the independents on the Toronto Escort Review Board and look for one to guide you through some basics.

God and the Straight

Dear Sasha,

I am 42, and my wife is 37. We have been married 12 years. We never had a great sex life. I have always suffered from premature ejaculation because of our once-or-twice-a-month sexual activity. Here is what our problem is:

1. My wife takes a very long time to reach orgasm, usually about an hour with oral stimulation, although she prefers vaginal intercourse over oral. If I try vaginal intercourse, the only way she can have an orgasm is by laying down flat on her back with me on top, but then she has to squeeze her legs to achieve orgasm in this position. It becomes hard for me to penetrate her, while she expects a good half-hour of penetration in this position. If I try any other positions, she doesn’t feel much. I’m an average 6 inches. Maybe size is an issue. Sometimes I remark to her that she definitely needs a bigger size, and she laughs. She hates toys, never even wants to try them.

2. She is always wet down there, so she has to use panty-liners. With very little stimulation she gets very wet and starts dripping.

3. She feels that if she gets penetration for 40 to 60 minutes, she will feel more satisfied. I do not have this kind of stamina. She is religious and conservative, with no history of sexual experience before marriage. 

Can you advise?


It sounds like you and your wife got married with little to no prior discussion about how your sex life would look. This isn’t unusual for highly religious couples. The problem is that most religions are extremely confounded by the topic of sex, so relying on yours as a guide shuts down any possibility for your sex life to change and grow naturally.

When consensual pleasure is viewed as sinful (oral sex, for example), you know you’re going to have trouble integrating it in a straightforward, natural way.

Also, many people are wary of altering their “method” of orgasm. They’ve carved that pathway, and they’ll be damned if they’ll let anything interrupt them on their way to that goal. Here’s the thing: generally, you have sex with someone, not at them. You need to engage her in the process of change, compromise and exploration. Requiring things to be just so is one way of cultivating a very resentful and alienating atmosphere.

However they’re behaving and whatever they look like, please don’t be suspicious of or mean to each other’s genitals. They’re the good guys. They didn’t ask to be assigned to people who imbue them with wicked intentions.

I often feel my hands are tied when advising people whose sexual identities are influenced by arcane, obfuscating and sexist religious doctrine, Festering. As an atheist myself, I find it exasperating and believe, to steal from Trudeau, that religion has no place in the bedrooms of the nation. I wish you the best of luck navigating your sex life in such a contradictory framework.

Open Your Books

Dear Sasha,

I ordered the book Opening Up that you recommended for open relationships and wonder if you can suggest other references.


Absolutely. There are a couple of classic tomes in the open relationship canon that might interest you. The Ethical Slut, by Dossie Easton and Catherine A. Liszt, is one, as well as Polyamory: The New Love Without Limits, by Deborah Anapol. Wendy-O-Matik’s Redefining Our Relationships is also good.

I encourage you to read Andrea Zanin’s reviews of all these books, from her own very poly point of view ( Her take on Tristan Taormino’s Opening Up is particularly interesting. Zanin thinks and writes very thoroughly about this shit. I seriously don’t know where she finds the time to fuck or if she’s one of those enviable people who can multitask — fuck and think at the same time, possibly getting one of her lovers to transcribe.

Sasha Van Bon Bon

Sasha is a nationally syndicated sex columnist whose work has appeared in a variety of Canadian weeklies and online magazines for over 15 years. Her column appears weekly in NOW magazine. She is also...