Canadian gigolo

Sasha gives advice to a would-be male escort and a woman experimenting with a polyamorous lifestyle.

Hi Sasha,

I’ve been thinking about becoming a male escort exclusively for women. I’ve searched the Internet, and I gotta admit I didn’t like most of the websites I saw. was somewhat fine, but are there other ways to get started? I mean, I want to have a classy approach towards this (lacking in most websites), and I also want my eventual lady-clients to feel they are hiring someone with class who has a genuine interest in pleasing them and being good company for them.


Dear Jeff,

I spoke with Alex S. Logan, a self-described luxury companion for ladies. Here’s what he had to say:

“The first thing any prospective male companion has to answer is, are they comfortable with the idea that the lady is choosing him, and he is not choosing the lady? Are they able to understand that not every lady has the looks of a model? If the answer is not unequivocally yes, then the odds of success in the endeavour are close to zero.”

Like with any business, a short-term investment (this can actually take a year or more) is required to obtain a long-term result.

“Getting started does involve creating a website,” says Alex. “How a companion presents himself is critical — a clean look with the relevant information, grammar, spelling, providing a sense of who you are and what might make an experience with you special. A willingness to engage with ladies via email or phone over some time so they can get a sense of you. The market for male companions tends to be longer dates, not one-hour sex fests. Are you ready to spend multiple hours with a relative stranger?”

Alex also suggests you have a look at this website — “a discussion forum that is exclusively dedicated to male companionship for women.” And I suggest you look at his website, especially the etiquette section. Alex has done a really good job of presenting himself in a direct and appealing manner. Other existing or potential male escorts, take note of this: the photo of you holding your iPhone in your bathroom mirror is some lazy bullshit.

What is often most taxing about being an escort, Jeff, is not necessarily the work itself, but the uncompensated work around it. As Alex says, engaging with people via email or phone is an important way to establish a connection, but it does not always lead to a date. It can be both draining and vexing to spend several hours establishing a professional yet intimate connection with someone only to find they are wasting your time. You must really learn to let your frustration go and, at least at first, make sure you don’t rely on this as your primary source of income. It may take you years before you establish financially rewarding credibility.

Also, if I may add two last things: when you choose wording for your profile, please recognize that those who use the word “classy” very rarely are, and when you come to the part where you talk about client confidentiality, please spell “discreet” the way you intend to mean it in this case: tactful, not separate.

Lessons in polyamory

Dear Sasha,

I’m a 27-year-old bisexual woman and I’ve been seeing another woman (23) for about two months. I also have a boyfriend of six years. They know about each other, though they haven’t met. This is my first “real” relationship with a woman, and hers as well. Everything is amazing, except that she’s extremely jealous of my boyfriend. It’s obscuring all the awesome things about being together. She gets fits of rage and cries, but says she wants to be with me. What can we do to make it work? Or are we doomed to fail? Would it help if they met each other? Please help — I don’t want to lose this girl!


Dear Me,

This is all part of the process of having sex with multiple partners. Everyone has to accept they will have the part of themselves that wants security, comfort and commitment from one partner worked over with a cheese grater. Everyone needs to take responsibility for their own shit and also know that often nobody does; they just talk about taking responsibility for their shit and then they do irresponsible shit that everyone needs to spend three weeks bawling about afterwards.

I know — applying dispassionate, selfless ideals to this chemical stew is like trying to calm a tantrum-ing child with a broccoli floret, but it is part and parcel of being poly. You all have to get past the idea that “if you love me, you’ll only want to be with me.” It can be very uncomfortable. Because it requires a lot of negotiating, it can also feel really artificial.

I do believe that some people are more predisposed to non-monogamy than others. I, for one, am terrible at it. I tend to be attracted to people who choose this model because it allows them to spread their emotional inaccessibility out over a group, rather than having to confront it head-on with one person. Unwilling to accept that I simply need to stop pulling my chair up to people who are delectably out of reach, my next manoeuvre is to then systematically insult and belittle all of their other partners (“Really? A spoken-word artist? When you have sex, do they come in that jolting, staccato cadence?”) in the hopes that I am the last one standing. Guess who’s single now.

I don’t want to condescend, Me, but you guys are young, so you are in nascent stages of your poly history. This doesn’t mean that the older you get, the better you get at it (though many people do), but you are going to have to garner experience to know what all the shades of poly look like. Emotions can be overwhelming, which is why poly people like schedules and rules. For example, when you arrange a meeting, make sure that you’re not shitfaced and that there’s a precise timeline. Do it in a public, neutral place so that everyone is more inclined to behave. Be strong in your intentions. Don’t pit partners against each other for excitement.

Personal introductions can be scary but people are way less frightening, and you can build up way less uninformed and cruel judgments about them, when you meet them face to face. Your lover is young, but she also has to know she can’t just go flipping out all over the place whenever the mood strikes her. 

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