I'd appreciate your thoughts on a matter of sex worker etiquette and social boundaries. Someone I'd describe as an acquaintance/casual friend recently let me know that she is working as an escort. I've known her for a few years, and have always been more than a little attracted to her. We dated very briefly when we first met and have had an intermittent friendship in the years since. We're close enough to talk about subjects like sex work and our mutually non-judgmental attitudes toward it, though this is someone I bump into fairly rarely—maybe a couple of times a year. If there's an appropriate and respectful way to bring up that I'd be interested in her professional services, I'd love to do it in the right way. Or would you advise me to leave this alone? We're well enough acquainted that I could broach the subject in an in-person conversation or by text (as opposed to, say, booking an appointment anonymously and saying "Surprise! Remember me?"). Any thoughts?

Friend In Favor Of Compensating For Benefits

I have some thoughts—I always do—but in your case, FIFOCFB, the thoughts of actual sex workers should carry more weight than mine and would doubtless have more value. So I tossed your question on Twitter, tagged some smart and insightful sex workers I know, and sat back and listened as they kicked your question around on Twitter. I've edited their responses for pace and clarity, FIFOCFB, and you'll find them below. If you're interested in sex work—as a profession, as an issue, as a cause—you should be following these folks. (Some names I don't recognize jumped into the conversation, FIFOCFB, so not everyone on this list may be a sex worker. But everyone was smart and helpful and you should follow them all.)

@MistressMatisse: My answer to @fakedansavage's reader letter is: I personally do not accept people as clients if I've been friends with them socially. But that is partly because I'm a dominatrix and some fantasies and D/s rely on a certain level of mystery and distance. Definitely via email, NOT in person. Tell her it's cool if she doesn't feel comfortable. And accept it will change things.

@BringMeTheAx: "How's business? Are you taking new clients? Would you be open to seeing me professionally?" Best approach I can think of. As mentioned, the prior relationship could make it awkward. As any client should, if she declines to see him, LW should accept that graciously.

@MissLaraBelle: I would choose one of the zillion other SWs where boundaries are not an issue. The question can be broached: "Are you open to seeing clients who are part of your personal life," etc., but don't even go there at all if he expects her to keep it a secret and have a whole range of new pressures forced upon her with her other friends/acquaintances.

@MistressMatisse: He said he only bumps into her a few times a year. That seems manageable.

@MissLaraBelle: She might study with his sister or something though, it happened to a friend.

@MistressMatisse: So she can say no. And he should be very cool about that.

@Maggie_McNeill: It's a delicate one. If they had never dated I'd say it was pretty straightforward. But as it is she could conceivably feel awkward. My advice: He should tell her he'd like to see an escort and ask if she has any recommendations. Then IF she's comfortable, she can volunteer her own services, and if not he'll get a very good recommendation to another.

@RosemaryLashes: I had a friend ask this of me when I came out and frankly I find it insulting. For me, I want compartmentalization. I do not mix business/clients w friends. It complicates too much, and $ creates power dynamics regardless of intention.

@AvaGraceVIP: Definitely don't surprise her with a booking without notice. But considering the history of the friendship you can always ask the question. If she's not ok with it she will say no. And you need to be prepared for and ok with accepting that no if it comes. Good luck.

@strangerswmandy: Every SW is different but to me the "used to date" part gets a little dicey, there are plenty of other pros to seek, always

@melodienelson: Sex—paid for or not—can change relationships. But he should ask simply. No more stigma 1 day.

@ConnerHabib: Yes, he definitely has the right to ask! But I want him to ask himself why he's asking, too! I'd ask: Out of all the escorts in the world you can hire, you chose one whose boundaries may be problematic for you and would need negotiation. What does that tell you about yourself? Self-investigate & move on.

@MistressMatisse: He wants a situation where he feels safe. He may/may not get it but asking seems OK.

@ConnerHabib: I guess I'd need to know more about their relationship. I can imagine a situation where that seemed right. Not reading it here though. Biggest problem for me is I read an "I'd get special treatment" vibe. But maybe that's not the case. That's why I'd like to know more.

@MistressMatisse: Well, he would get special treatment. He'd get the "I know you're not a cop, and I'm PRETTY sure you're not a serial killer" treatment.

@SensualMuse: IMO no on this—personal life is separate from work. To mix risks never having down time. It's personal. I think. Just my boundary preference. No clients in personal spaces.

@Joy_deVive: Refer them to colleagues, it's the professional thing to do.

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@SensualMuse: Exactly.

@MistressMatisse: Let's remember times are tough for some ladies. She might LOVE a vetted new client.

Listen to my podcast, the Savage Lovecast, at www.savagelovecast.com.