Dear Sasha,

I’m a guy in his mid-20s who has never gotten laid, and never seriously pursued it either.

I had romantic notions about how it should go down — and was a bit naive about my bi tendencies, which threw me — and just kept putting it off. I wanted to “invest” in a real moment with someone special. That’s still true, but I’m also eager to finally just get down with someone. After all this time, I think I’d be going in with a lot of expectations. Even if I just had a random fling, I’d risk walking away feeling stupid, having built it up for so long…or having given up on the idea that I deserved to be with someone I knew was really “invested” in me.

So my question is this: we always hear about how important it is for girls to wait and make sure they’re ready, but don’t some guys also take their time before hopping into the sack? Is it just as normal for a guy to wait it out until he’s got a handle on who he is before getting it on? And are those guys glad they did?

Man Still Waiting

Here’s just one of the many things I find curious about virginity: it is one of the few states of naïveté that precedes a pleasurable, vital activity wherein we feel our first attempt at it will set the official and incontrovertible tone for our lifelong relationship to that activity. Somehow, we believe lack of practice will make perfect, not the other way around. Bizarre, no?

As much as I appreciate the message that one doesn’t have to rush headlong into fucking, I would also like to mention from my own experience that it’s no big deal if you just go over to someone’s house and stare in listless agony at their Jean Harlow poster while they hump you. Many moments will mark your sexual journey, and your first time — good, bad, glorious, boring, confounding, frightful — does not have to be some flawless, defining moment. Let me tell you, Man, even those of us who heard doves cry on our first ride had many experiences after that didn’t live up to it. Or did. Then didn’t. Etc.

Good lord, for another example of a pleasurable, vital pursuit, look at food. Your first meal comes out of a tit. Do you think you can sustain that kind of epicurean excellence forever? Certainly not, but there are other inspiring ways of enjoying a meal.

Here’s another secret: you will never have a handle on yourself. And just when you think you do, all hell will break loose. You’ll want to fuck your way through some of these squalls, while at other times it will be the last thing on your mind. Sex is not something that robs you of self-knowledge; it adds to it.

Dear Will Munro


It has been a delight knowing you for the 12 years I have lived in Toronto. It has been lovely watching you grow, watching other people grow with and because of you, and following your chaotic yet serene career and life.

Thank you for being part of the nascent stages of my own creative life in this city when I first began doing burlesque. Thank you for providing the Scandelles’ first stage for Neon Nightz at Vazaleen, even though that stage was made of an old futon base and a broomstick. (And although I was outraged by this makeshift platform, I never imagined for a second that it would be anything but plunder you’d hauled out of a dumpster and dragged down the street behind your bike.)

I have been thinking a lot about your last two years, when you, so independent and self-sufficient, allowed yourself to be vulnerable enough to accept what I could give you — love in the form of fanatically prepared food. Though we never spoke of it openly, I think we recognized in each other someone who had a hard time accepting help. So thank you for letting me hug you through quinoa stew. This gift you gave me, the knowledge that in order to affirm your humanity you must first allow yourself to be human, is a lesson I carried through a very rough time myself.

I would also like to thank the beautiful men in your life for standing up at your memorial and sharing their passionate stories of romance and love. To their parents, for openly calling you lovers and respecting that that’s what you were: men in love, full of depth and tenderness and desire.

Men are not unbreakable; they should not have to be. Breakable men are strong, enlightened men, men who speak of love as though it is the most important thing in the world, who find strength in holding one another. These are the men you have been with, and they will always be this way because of you. I was so touched by this, reminded of the stir of young love and how we must all strive to respect those who have loved our partners well.

To watch your lovers honour one another and their shared intimacy with you was remarkable. Remarkable in that not a touch of covetousness or apprehension defined their connections, only deep esteem. The intense admiration they showed for the coterie of queer women with whom you surrounded yourself spoke to yet another aspect of your exquisite nature. You were indeed a lesbro.

The guileless ferocity with which you embraced your deviance galvanized us all. You led by following in the footsteps of those who came before you, and to them you offered unmitigated respect by providing a stage, a space, a renewed voice. We will all do the same for you. Our will lives on through your name, you dazzling little shit disturber.

And on that note…

Just sayin’.

Ask Sasha: [email protected]

Independent rukus-raising news site seeks new friends (at $5/month) for support network. rabble will always be there for you, looks pretty good and has a winning personality.  Loves new friends and will shower them each with a free independent print magazine subscription.  Contact at  No photo required.

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...