Good answers from the guest experts. Always great to hear from MistressM. Her point re him probably not being a serial killer is a bit chilling.

I gotta go with Rosemary on this one. While I am not a sex worker, I have worked in the customer service industry. When the relationship goes from friend to client or client to friend, things never seem to end well. I too suspect it is due to money and the power issues that arise from it. Not suggesting that either party in this situation are not credible people, but it is very easy to blur that line and find yourselves wondering what went wrong. OP sounds like he is just into the sex worker, why not just ask her over?

As a female who isn't a sex worker, but who has male friends (without benefits), this squicks me out. LW comes across - to me, at least - as sounding entitled, desperate and opportunistic. That probably doesn't distinguish him from a lot of men, but it's still not appealing. If his friend really needs the money, I can understand why she'd say yes. But in an ideal world, one where sex work were normal and legal and socially acceptable, I still think this should be a "no".

I particularly liked the one from probably-my-favorite-porn-star:

@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.

Hopefully, if the guy is self-aware enough to write to Savage Love in the first place, he's self-aware enough to ask himself these questions & answer himself honestly.

LW, if you have always been more than attracted to her, yet only dated briefly and have a casual friend/acquaintance, sounds like she wasn't that into you, right? Hire someone else, if she sleeps with you because she needs money, you will just be a john from now on, no longer a friend, however casual. And if you want to hire her because she rejected you before, DON'T do it. Resist the urge to be a POS! Life is short, try to get through it without hurting people.

IDK why they're all so mystified about "why her out of all the SW". She's someone he's lusted after for years, struck out when they dated, and now finds it may still be feasible to get a fuck from her.

@6 right, the question is whether he understands his motives and understands that he'd be getting a fuck and nothing more. Less than nothing, in that it will squelch any friendship here, probably. If he's got any hint of wanting to buy the relationship he didn't get, don't go there. If he's going to get attached or obsessive or possessive, don't go there.

Has he ever had FWB sex before with a friend he previously had a thing for? And had that go well? Because that's easier than this.

I liked the suggestion to ask for a referral, and she can refer to herself if she wants to.

Most sex workers their work and private life strictly separate. If he asks and she accepts him as a client the friendship will probably be over.

KEEP their work and private life separate , sorry.

Also, many sex workers don't have a very high opinion of their clients. I doubt that she'll appreciate someone she thought was a friend wanting to be her client suddenly. Especially the fact that they used to date is shady. As if he thinks "If I pay her I can still fuck her".

Pretty obvious that the guy wants a girlfriend without the bummer needing to prove yourself stuff. He needs to keep this thought in fapland.

ConnerHabib: "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?"
That he prefers to have sex with someone he knows and likes, I'd say.
So it's just as obvious why he would want her as why she wouldn't necessarily want him.

I'd be squicked out be this. It seems to me like he's saying, "you considered fucking me for free and decided you weren't into it. So now I'd like to pay you to fuck me, even though I'll know the whole time that you are absolutely not into it."
I mean, of course one always knows that a sex worker is doing it for the money rather than for lust. But in this case, he'd really really KNOW it. I can't imagine wanting to fuck someone, especially a friend, knowing that they were not into it at all.
It reminds me of years ago when a friend became a stripper, and a bunch of mutual guy friends started going to see her dance. These were all guys who shed turned down dates with, but now they got to see her naked anyway and she couldn't stop them. She said it bothered her 1000x more than the most lecherous strangers. She finally quit that club and went to a different one, and tried to keep anyone from finding out where.
Of course this woman has the option of saying no, but I have a hard time imagining a friendship lasting through, "I know you don't want to fuck me just cause you like me, but, well, how hard up are you for cash?"

Why did she tell him this? Maybe it is just friends sharing information about their life.

But maybe she's seeking clients. There seems little doubt that she knows he is attracted to her. Perhaps she views the letter writer as a relatively low-risk potential client.

Sure, if she is offended or squicked it might ruin the friendship. But he sees her like twice a year. I don't think it would be *such* a transgression to subtly inquire if she is seeking new clients, and if so, if she would consider the letter writer. He seems respectful enough to back off if she says no way. And if it ruins their tenuous friendship, oh well. Make some more friends, preferably ones you aren't not-so-secretly pining to fuck.

Smoakes @12: "I'd like to pay you to fuck me, even though I'll know the whole time that you are absolutely not into it."

I'd like to refer you to a comment from a few days ago:
http://www.thestranger.com/slog/2016/07/…
@92/@93: "there is a nugget of truth that at some level, I'm inclined to believe that anyone I find attractive must be interested in me. I'm pretty sure it's a guy thing"
"men believing that women must want to sleep with them despite all evidence to the contrary is a real thing in my experience."

So it's possible that FIFOCB would not know the whole time that his friend wasn't into him; he'd convince himself that she was into him, and that her previous lack of interest was just... bad timing? Who knows.

I have a hard time imagining a friendship lasting through, "I know you don't want to fuck me just cause you like me, but, well, how hard up are you for cash?"
As an accountant whose friends frequently ask whether they can pay me to provide my professional services, I can easily imagine this. She just has to say what I do, which is, "Sorry but I'm not taking on any new clients at the moment. Can I refer you to someone else?"

She just has to say what I do, which is, "Sorry but I'm not taking on any new clients at the moment. Can I refer you to someone else?"

Your friends asking you for your professional accounting service is not in itself something which would endanger a friendship (I'd guess). From what I know of the relationship between sex workers and clients, someone who she thought was a friend asking a sex worker for her professional services might very well turn the friendship sour.

I'm with @MaggieMcNeil, mention that knowing she is a sex worker has got you thinking that you might like to give it a go with a pro, but are a little leery about approaching a total stranger. Any suggestions on how to proceed? This seems like a distant friendship, not inner-circle stuff, so let her decide if she wants to throw her own hat in the ring.

I don't understand why people think this is a friendship and/or previous dating relationship. He thinks they're causal friends, he has her phone number, he took her out to dinner this one time and paid for it so it was a date, but he never quite managed to get a second date. She would be hard pressed to remember his name out of context, vaguely remembers the time he paid for her dinner and thought it was sweet but so not happening, and probably didn't even save his phone number.

I don't think there's a problem with asking, and I wonder if when she "let him know she was an escort," she was thinking of exactly that. If he were to ask for a referral to another sex worker, though, I think it would be somewhat unprofessional to offer her own services - so as usual, being clear and upfront, and, if it happens, taking rejection with grace is the way to go.

Maybe I am misreading American relationship lingo (wouldn't be the first time) but I interpret We dated very briefly as "we had a brief romantic relationship", not "we had dinner once".

Wrong interpretation?

Mention what you're interested in and ask if she'd be interested in taking you on as a client OR if she knows a colleague who she could recommend you to. That way if she's cool with it she can say so, but if she feels uncomfortable she can avoid a lot of awkwardness by making a referral and leaving it at that. (Assuming of course that FIFOCFB is a decent guy whom she trusts.)

RE @18: If you're interpreting "romantic relationship" as "sexual relationship," I think you're misinterpreting. It seems pretty clear they never had sex, though he always wanted to. Whether that's no sex over the course of one dinner or several, I'm not sure, but "we had dinner once" seems a plausible interpretation of "very briefly."

TND123, unless you're the LW or the escort, you're making an awful lot of assumptions. "We're close enough to talk about subjects like sex work and our mutually non-judgmental attitudes toward it" doesn't fit your "she would be hard pressed to remember his name out of context."

RE: If you're a sex worker, I'm presuming you're quite used to dealing with requests and conversations most people would find objectionable. "So, are you taking on new clients?" is probably among the tamer questions she gets asked.

BDF @21

If you're a sex worker, I'm presuming you're quite used to dealing with requests and conversations most people would find objectionable.

Of course. But because of the tendency of sex workers to keep private life and work strictly separate, she might not appreciate a friend making a "professional" request, even a tame one.
Maybe the LW should first try to find out where his sex worker friend stands on the separation of work and private life before making actual requests.

@21: ""So, are you taking on new clients?" is probably among the tamer questions she gets asked."

That doesn't make this question respectful and healthy to the friendship by comparison.

@18: I'd generally agree, but considering the LW's intentions his boundaries are questionable and I wouldn't be able to make any educated guesses on whether she had coffee with him or anything moe involved on her end. I would however assume there was little romantic interest on her end and no sexual activity if he's asking this question.

Undead @23: It's hardly a friendship. "This is someone I bump into fairly rarely—maybe a couple of times a year." This is an acquaintanceship.
Many friendships survive one person taking the risk and asking the other person out on a date or making a drunken pass. I don't see how this is much different. So long as he acts as if she is perfectly within her rights to say no, which he does seem to understand.

And "I don't understand why people think this is a friendship and/or previous dating relationship"

Because he's positioning it as that in how he framed the letter.

"he has her phone number, he took her out to dinner this one time and paid for it so it was a date, but he never quite managed to get a second date"

He obviously knows her beyond this, he's maintained a "friendship" and she trusts him enough to discuss sex work matters in private. They're not besties, but he knows her IRL and she would certainly remember who he is.

@25: Eh, I mean he doesn't care about torpedoing what they have, but her not being interested in continuing as a partner doesn't mean that he deserves a shot by paying for the privilege. That he's not asking for referrals directly just seems odd. I have no clue what the etiquette is for these scenarios but the other professionals polled sound skeptical. Probably because the power dynamic is different when she chooses to not continue as equals versus starting from the job aspect and her having the ability to select from the get-go and then getting to define their sexual relationship?

Encouraging him to pursue when she's already declined his advances seems a bad decision in the making.

My sex work experiences are not all sex workers' experiences, but I had a friend/acquaintance ask if I'd see him as a client, I wasn't squicked out, and I even gave him mates rates (although I sorta regretted that because getting him off was a bit tiring). He was someone I'd kissed when we first met, but it wasn't a kiss that made me want to sleep with him. When he asked about making a booking I said no because I thought it would be difficult for him to deal with, but he convinced me that he was in the right headspace. I fucked him, it was fine, I didn't find I wanted much of a friendship with him but not because he'd once paid me for sex.

Compartmentalisation was never my style. I was always more or less me with clients, and it was never a secret that I was a sex worker. I also never looked down on my clients (or customers, when I was a stripper). Some were great, some were nobheads, most were pretty normal - much like those of us who sell it. Going by other comments, maybe think about where your friend seems to be on these issues.

I think the closer I was to someone the less likely I'd be to accept, though. Keeping emotionally detached from work was natural for me, whether it was super hot or icky or whatever, but I wouldn't necessarily expect the same from clients so there's definitely a chance that it'll get in the way of a friendship. If I really cared about the friendship I wouldn't risk it for some cash and giving someone something they thought they wanted.

So, I can't be friends with my plumber either????

I think if he wanted to be seeing random sex workers, he'd already be seeing random sex workers. He wants THIS girl. He doesn't want a referral to someone else.

@29 I don't know. Ask your plumber.

Wow. Lots of sex-negativity and sex negative stereotyping about both sex workers and sex-work-seeking-clients going on here. Not from everyone, but enough to make me write this. This guy is seeking a sex worker. Has a friend who is a sex worker. Surely both of them are mature enough to work this business transaction out? A lot of you seem to believe he's trying to get something he "doesn't deserve" and that she's so ashamed of what she does that she can't possibly do her job without getting all her feelings about some random friend muddled up.

Maybe some of you here should re-read your comments and then re-evaluate your judgmental attitudes about sex work (and clients of sex workers)?

Damn. I expected much more open-mindedness from readers of Dan Savage here. What a disappointment.

"that she's so ashamed of what she does"

This claim, that nobody but you are trying to state, says much more about you than it does is.

I have been a client of sex workers for decades and I have been hanging around on forums visited by both clients and sex workers for 14 years. Sex work is legal where I live but it is not socially acceptable, not for the workers and not for the clients. It is a kind of underworld where there is a lot of mutual distrust and contempt between clients and workers. (Not always, but often enough.) I hardly expect things to be better in a society where sex work is actually illegal.

Wishing that it was all a happy-hooker scenario doesn't make it so. LW should tread carefully.

@33,
Plenty of others are making that claim. That she's incapable of doing her job without getting emotional about it. This is a business transaction. Period. Either she'll do business with this client or she won't. If she's mature and professional, she won't let her feelings interfere with her work. Women ARE capable of doing that, you know.

Lots of man haters on this site too. You appear occasionally to be one of em. This guy writes a very respectful and non-threatening letter asking if and how he should ask his friend if he should do business with her. You jump to the conclusion that he simply MUST have some ulterior motive to get what she denied him in the past. Shit. For all you know, his motives are simply: 1) Since he knows her, he knows she's not a cop out to bust clients, 2) he knows he's already physically attracted to her, 3) it's potentially easier to have sex with someone you know at least somewhat rather than an utter stranger, and 4) he's personally contributing to her career and livelihood. You make him out to be some self-centered lout when his letter comes across as humbling and genuine.

I love that you think this is about "hating men".

Self-centered, clueless and totally sincere are all not mutually exclusive.

I don't think it's likely to work out, I don't think he's a horrible monster.

"Sex positive" doesnt mean thinking every single pairing in every single context is a good idea and worthy of recommendation to the LWs.

So this actually sorta happened to me from the customer's perspective. In a gay context.

There's a guy I met through mutual friends who I had a mild sort of crush on. Then he started to go-go dance at some of the gay clubs, so I got to see him dance in his underwear and tip him. We were friendly and on a first name basis, and would chat when we saw each other out, but didn't hang out outside of clubs and really only saw each other every few months.

Anyway, I stopped going out so much and hadn't seen him in a year or two. Then my roommates were planning to be out of town and, thinking I might take steps to relieve a long drought, I started perusing listings on a gay escort site. Lo and behold, he had an ad up (or someone using lots of photos of him had an ad up). I wasn't sure if it was really him or if someone had stolen his photos.

I hemmed and hawed for a long time. I wasn't sure if it was legit or a stolen photo situation, and I felt weird contacting my friend through Facebook to find out. I had always wanted to see more and do more with him out of his underpants (having seen him go-go dance but not more than that) but wasn't sure if it would be weird.

After thinking about it for some time, I finally messaged the person through the escort site and arranged to set up a time when my roommates were out of town. Once we had set things up, I messaged back and told him that I knew him in real life, told him who I was, and told him that I totally understood if he felt uncomfortable going through with it.

Turns out that it was legitimately him. He was cool with going through with it. Maybe things are different in the gay world. Maybe it's because we were more casual acquaintances than close friends. Maybe he felt he knew me well enough to feel I wasn't a stalker or anything. I dunno. Anyway, I got to see him out of his undies, I got to do things with him, and afterwards I got to try out my remodeled shower with a cute guy.

That said, I doubt I would have contacted him if we were closer friends. From my end, the casualness of our friendship helped.

One more maybe ... maybe he was okay with it because even though we met in a different context (at an event at my house, actually), I also already knew him as a go-go dancer. If I only knew him through school, or work, or brunching with friends or something like that, perhaps then it would have been weird. Perhaps the fact that I'd already put dollar bills in his underwear while he was dancing on a box had "broken the ice."

@38: "Maybe things are different"

I can see that, I have a friend that occasionally dabbled and would have zero issues getting some extra cash for someone he knew that he'd enjoy sleeping with anyway.

"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."

Well, sure he can ask. But I think that there are some potential motivations that would make her wary.

1) He might hope that as an acquaintance, she'll give him a discount.
2)) It does read as though he would have liked to continue (or start) having sex with her, and she wasn't interested and now he figures that as a paying client, he'll "get" something she didn't want to "give" him in a non-transactional way.

Now it might be that he feels safe or comfortable with her, and it might also be that she'd feel safe and/or comfortable with him, but it will shift the relationship to a client and service-provider, and I would imagine that would be the end of the friendship, casual as it is.

I'm not a sex worker, but I have friends who are and they don't socialize with their clients. They also have told friends that they do sex work, and their telling them that isn't an attempt to solicit their friends. Once you start having sex with someone in a kind of obligatory way, I can see that you would, as Registered European says, develop some contempt for them.

Basically, she's had the opportunity to have had sex with the lw for years and if she wanted to for its own sake or because she's attracted to him, she would have. Maybe he wouldn't be bothered by the knowledge that he's only getting to have sex with someone who didn't want to have sex with him just because, but maybe he hasn't thought this through and he really would.

She is certainly able to tell him she's not interested in that relationship with him and she can offer a referral, or she can say yes. It seems a pretty low-stakes question; since she has told him she's working as an escort, it doesn't seem likely she'll be offended by his asking to book a session.

But yeah, just booking an appointment anonymously and saying "surprise!" when he got there would be an ultra-stupid move.

Seems odd, and unfortunate, to me that sex workers would develop contempt for their clients. I guess I can see it from a point of view of "some of my customers are idiots/assholes" in the way that people in all other businesses sometimes do, but I'd assume that only happens if the client really is an idiot/asshole. Otherwise, you're just hurting your own bottom line by holding your paying customers in contempt. What's so contemptible about a sex worker client anyway? I don't get it.

"Otherwise, you're just hurting your own bottom line by holding your paying customers in contempt. What's so contemptible about a sex worker client anyway? I don't get it."

A lack of empathy, likely.

Customers outside of sex work can be shitty enough. Why wouldn't some be less enjoyable to work with than others?

Empathy is unnecessary. Nice but unnecessary. As long as the customer is respectful, professional, and timely, empathy doesn't really play a role.

If I hire a mechanic to fix my car, I expect him/her to fix it to specifications in the time promised. Likewise, the mechanic expects to be paid for their work in full, on time, and treated with professional courtesy. Empathy doesn't come into the equation. Bonuses or tips or referrals from the customer are an option if service is exceptional and preferential treatment from the provider are an option if the customer is exceptional. But they're neither a requirement nor should they be expected.

Sex work is no different. Business is business.

@44: Actually, sex work is different.

Y'know, if LW's friend wanted to keep her personal life and professional life completely separate, she wouldn't have told him in the first place. This isn't him stumbling across her ad out of the blue. This is her consciously revealing what kind of job she has.

Given that, I'd guess that someone who's comfortable telling you what they do for a living will also be comfortable with you asking if you can patronize them. They might not be comfortable being patronized, but in that case it's trivial enough to make up some excuse why they're not available.

@45,

How so? It's an exchange of goods, no? One person's time for another person's money? Sounds like almost every other business out there.

UF @42

Seems odd, and unfortunate, to me that sex workers would develop contempt for their clients.

A few possible reasons:
Some clients, especially those from more patriarchical cultures, have a low opinion of "whores". After having paid, they feel they can do with them as they please.

Societal opinion says: only a loser will pay for sex, because he has no other options. So a sex worker has to earn a living by having sex with "losers" who are often old enough to be her father or grandfather. And she has to pretend to like it.

The money. Sex work can be a kind of "golden cage": the hourly wage is much more than can be earned in most "normal" jobs. So even if you'd rather stop, actually doing so can be very difficult because of the substantial pay cut you'll have to endure. Many sex workers keep working reluctantly because they got used to the money.

Urgutha @35: How does "Plenty of others are making a claim that she's incapable of doing her job without getting emotional about it" (citations requested) equate to "she's ashamed of what she does"?

Nocute @41: "since she has told him she's working as an escort, it doesn't seem likely she'll be offended by his asking to book a session."
Bingo.
Mentioning that I'm an accountant means people at parties ask me about their taxes.
Mentioning that one is a plumber means people ask one about their boiler playing up.
Mentioning that one is a doctor means people ask one about their health problems.

If she truly were "ashamed of what she does" she wouldn't have told this casual friend, would she?

What new information is she going to get out of his asking if he can contract her services? The knowledge that he'd like to have sex with her? Presumably she already got that vibe years ago.

I think a lot of people are projecting; if one is not a sex worker, then yeah, "may I pay you for sex" would be really, really creepy. But if getting paid for sex is what one does, receiving requests to be paid for sex is part of one's job.

"I think a lot of people are projecting; if one is not a sex worker, then yeah, "may I pay you for sex" would be really, really creepy. But if getting paid for sex is what one does, receiving requests to be paid for sex is part of one's job."

We're certainly reading in because of the short period of dating and statement of friendship along with knowing very little of either's personality. It could work out and she could find/set professional boundaries, but that he wants to be taken on as a client after feelings developed from his short relationship... that's why it seems like a referral is the idea most likely to work out (even if that's not what he wants.)

It's certainly an incomplete set of data to work with.

If it were that easy — “I want to hire a sex worker. Hey, I happen to know one socially and I like her” — there would be no letter to Dan. He would just contact her, introduce himself and negotiate (whether an appointment or a referral).

The fact is there is a letter to Dan. That tells us there’s something else going on. He’s apparently got a good angel on one shoulder telling him not to be a creep and a rationalizing angel on the other shoulder telling him that it’s just business and businesspeople don’t have feelings.

That’s why we’re advising him to listen to whatever it is his good angel is saying.

I know a sex worker socially. They’re nice and smart and attractive and they’re the first person I would think of if I wanted to hire a sex worker. (They are the first person I refer to when friends want to hire a sex worker.) Thing is, I know their parents socially too, and it would just be weird. I respect the little “nah, it would just be weird” voice in my head and get on with my life. No letters to Dan.

venomlash @19 +1

There's all this talk about removing the stigma from sex work and how it should just be a profession like anything else. Yet, all I read in these comments are how creepy this dude is for wanting to hire a woman he knows for her services. If it's really just a profession (I think it should be), then why is it even a question?

And don't give me the line about "private and personal lives separate" because that's not the case for a lot of self employed people. Self employed people need their friends and family to purchase their services and spread the word. That's how a lot of people grow a business.

Also, he probably chose this sex worker "out of all the sex workers in the world" because he knows her, trusts her, and is attracted to her. There's lots of people that can't jump into bed with just anyone and he is probably one of those people.

If I were in his situation, I would ask her how she chooses her clients and what things would make her say "no." She very well might be open to performing her services to a casual friend.

The one-line summary: the difference between "I've been interested in hiring a sex worker, and now I know one", and "I've been interested in having sex with this woman, and now maybe I can."

@53 if he is a "can't jump into bed with just anybody" person, then it would make sense that if he has any interest in hiring sex work, this woman is a unique option from his POV. I'm just gonna say the odds are, though, that he *could* hire other people and have casual sex, he's just more into this idea. For various possible reasons, some of which would make hiring her likely go fine, and others less fine. So he should think about which he's got.

I do like your "how your filter your clients" approach. As long as it's not used trying to be a super-chill totally hypothetical question.

Alison @51: The good angel apparently told him to write to Dan.
I'm willing to defer to the experts, but the experts aren't in agreement. Some of the sex workers are saying, no, but some are saying a casual acquaintance is a safer client. We don't know which sort of sex worker LW's friend is. I agree that he should approach it indirectly, for instance by asking, "Would you ever accept someone you know as a client?" Then she can either say, "Eww, no way" or "Sure, pre-vetted clients are the best," and he can proceed or not from there.

I'm a little surprised by the chorus of "No, it's a bad idea". Seems like a great idea to me - she may turn him down, but he seems willing to approach it respectfully and realizes he may get turned down. I didn't read any questionable vibes in the letter.

I did sex work for several years, although I was a SW of the GFE variety and only saw a few, regular "boyfriends". I realize my experience and preferences may be different than that of other SWs. However, I had one long-time acquaintance approach me (actually he had a mutual close friend, whom he knew was already aware of my work, mention it casually to me while we were already talking about my search for a select few desirable clients - "hmm, what about 'Adam'? I bet he would be interested"). I thought it was a great idea, reached out to him, and we've carried on for several years now. While I know he cares for me, he has never tried to push a boundary.

This was a win-win for me. I knew he wasn't crazy or scary. He wasn't in my close circle of friends, so if things were awkward, it wouldn't poison our social group. While I wasn't interested in him enough to date him previously, (I always knew he harbored a crush on me), money sweetened the pot enough for me to take him on as a client.

I don't think it's fair to suggest, as a few people did, that she clearly isn't into it, and that it's creepy of him to want to have sex with her knowing that she isn't into it. There's an undeniable supply and demand aspect to it, assuming that she is an attractive woman. There will be plenty of men who want to have sex with her; if she is going to date someone (not as a professional) she probably has many choices, and maybe the LW just didn't "make the cut", so to speak. That doesn't mean though that she is disgusted by him or dislikes him. Money may sweeten the deal.

If LW has been carrying a torch for this woman since they dated a bit, and throughout the time that they have been casual friends, then I would suggest that he not reach out to her for sex work. In that case, he should simply ask her out socially, and if she says no, accept that answer gracefully, and decided whether to seek the services of another sex worker or not as the case may be.

On the other hand, if LW can truthfully say that he does not have any romantic feeling for his woman and he has been contemplating engaging the services of a sex worker, than I think he can follow the suggestions given to him by the sex workers who responded to Dan. In this event, LW gets the services of a sex worker who he feels comfortable with and knows. I don't think LW addressed this point, but it may be that he has never engaged the services of a sex worker before, which may be one reason that seeking the services of this particular sex worker is appealing to him. In return, as previously noted, this woman gets a client with whom she can feel safe.

@17: I think your entire comment was cut from whole cloth. LW says that he see this woman socially about 4 times a year. That may not make them besties, but I think that qualifies as friends.

@56 I agree. She liked him enough to go on a few dates, but she wasn't interested enough to get serious.
Then she told him that she found a new job, as an escort. That may have been her way of starting negotiations with a potential client.
@53 has the right idea. The LW should ask her how she chooses her clients, and find out what her boundaries are before asking for a booking.

@58: "Then she told him that she found a new job, as an escort. That may have been her way of starting negotiations with a potential client."

Is combing the phonebook for past dates and discussing your new gig common in that field?

That sounds more like Amway to me...

BDF @ 14, I'm honored to be quoted by one of my favorite Savage Love commenters and thanks for drawing my attention to the earlier responses to my post.

I do think it is very possible for a man to convince himself that the sex worker who previously dumped him is really into him even though he has to pay her for sex. Tons of men convence themselves that strippers and sex workers have the hots for them. Of course, it does occasionally happen that these women do develop feelings for a customer. I've read about incidents of it happening right here on Savage Love. But I suspect the number of men who believe that is happening outnumber the sex workers who have such feelings about 10 to 1.

For that matter, do you really think that this guy's sex-worker ex- considers him a friend? The see each other once or twice a year, apparently when they happen to bump into each other. I think the odds are pretty high that she thinks of him as an ex- she dumped who is still trying to get into her pants years later.

On the bright side for the LW, if that's the case, maybe that's why she mentioned the sex work and he can finally get lucky and he has no friendship to lose.

But if there is a real friendship, I suspect that asking for this, whether she says yes or no, would likely end or greatly diminish that friendship.

UF @45 and 47, Why is it so important to you to pretend that hiring a sex worker is exactly like hiring somebody to mow your lawn. It is not, never has been and never will be for reasons that are obvious to all of us, even if you won't admit it.

@49,
Everyone who says she might feel "squickish" about it. Or that it might ruin their friendship.

Why would it ruin their friendship?

@61,
For a long time I've believed that sex work should be legalized because it's just like any other work. Fucking is legal. Selling is legal. Why isn't selling fucking legal?

Apparently though, for reasons that are obvious to all of you, sex work is NOT like any other work. So tell me mr. obvious to all of us, how is sex work not like any other work?

Oh fuck it, I don't really give a shit what any of you think. It's really the inconsistency of attitudes and beliefs among so many of you that bugs me. See, I've always thought that women are strong and smart and capable of understanding the consequences of their decisions, and that they neither need nor want to be treated as inferiors. Thus, I've always felt sex work should be legal, because sex workers know what's best for themselves. However, for reasons that are obvious to all of you, perhaps women DO need to be treated with kid gloves... they can't handle the squicky feelings they might get if someone they know might ask them to do their job for them. It might even ruin the friendship!! Because why? Because women are incapable of separating friendship and sex and work?

I always thought women were far more capable than that... but for reasons that are obvious to all of you, maybe they're not?

and I'm outta here, this thread is dying. just chew on it for a while, k?

@59 I've never been a sex worker, and I've never sold Amway, so I honestly don't know.

I assume the LW's friend doesn't tell all her casual acquaintances that she is an escort, since it's illegal in most places and judgemental people may think badly of her. Who knows?

I would just ask her for a referral and be like "assuming you don't accept personal friends as clients..."

Makes it easy for her to reject you by just giving you the name of somebody else, and she doesn't even have to answer that particular question but you'll get the drift. Win-win.

DCP @60: Thank you!
she thinks of him as an ex- she dumped who is still trying to get into her pants years later.
No, I don't think so. He says they dated "very briefly." If I were to use that phrase, I would be describing a situation where, there was initial interest, we went for a coffee or dinner, had a nice chat, but there wasn't really a spark or I was interested in someone else or didn't have time to get involved or whatever, and neither of us asked for a second/third date, so it just petered out. I interpret from the letter that no sex ever happened -- that's why he's still curious about what sex with her is like. I would never think of someone with whom I had a chaste date or two as an "ex."

I completely agree that the overwhelming majority of men who think the sex worker/stripper/bartender fancies them are deluding themselves. Acting interested is a part of these jobs.

Undead @59: FWIW, I know my business is different, but if I hadn't approached friends and acquaintances as my initial client pool I'd have quickly gone out of business.

Urgutha @62: Firstly, who says it's only women who can experience complicated emotions related to sex? That's your sexist assumption. Secondly, different kinds of work are different. Have you only done one job your whole life? Do you come home with different aches and pains after sitting in an office all day than you do after working in a warehouse? Do police officers and social workers suffer emotional effects from their work in a way that delivery drivers never will? Thirdly, have you never heard the phrase "mixing business with pleasure"? Example, as noted, I'm an accountant. One of my lovers asked me if I would prepare his tax return, and I said no, because that would be a conflict of interest. Doing sex work for someone you chat with at parties may feel the same to her. That doesn't mean she's "ashamed of what she does" or emotionally weak any more than I'm ashamed to be an accountant.

How can you be so certain of how a complete stranger's mind works, in contrast to the people who said she "might" be squicked out? Those people are at least allowing for the possibility that, you know, she might not. Has everything to do with personal preferences, nothing to do with being a delicate flower. Aren't women, whom you purport to respect so much, entitled to make their own choices?

-- Quote Registered European #48: --
"Sex work can be a kind of "golden cage": the hourly wage is much more than can be earned in most "normal" jobs. So even if you'd rather stop, actually doing so can be very difficult because of the substantial pay cut you'll have to endure. Many sex workers keep working reluctantly because they got used to the money."
-- End Quote --

That sounds like a lot of attorneys I know.

@64: And this is hard to argue with, really. She knows herself and the LW better than we do.

UF @61, Because sex, unlike lawn mowing, is something that we usually only do with somebody we area attracted to or have feelings for? Because most people (particularly women) find the idea of having sex with someone not fitting those categories not just unexciting, but a little repellent? Because when most people look down on an activity, it affects the feelings and behavior of the people who participate in it? Because part of what is purchased is the ability to treat the seller in ways that you wouldn't treat a romantic partner and/or the ability to degrade the seller? Because millions of years of primates having sexually transmitted diseases have given us a predisposition to find something a little "dirty" about those human primates who have sex with dozens and dozens (or hundreds and hundreds) of partners?

We can all sit around and say that condoms prevent most STDs, sex workers provide a valuable service, it should be legal, etc. and that's all true. But the facts are that there's still a stigma around sex work and the purchase of an activity that is usually associated with emotional attachment is emotionally complicated for buyer and seller, with buyers frequently looking down on sellers and sellers frequently looking down on themselves.

And, while there are plenty of happy exceptions, there is a real correlation between a history of sexual abuse and strippers and people who sell sex.

Look, I'm not going to knock myself out here trying to come up with the world's best explanation of why selling dry cleaning services is a little different from selling BJs, GFEs and anal. If you can't admit that there's something a tad different there, you're not stupid, you're a liar.

Caveats: Of course I think it should be legal and try not to look down on the sellers and to be open to the idea that maybe some even some buyers have legitimate reasons, etc. And, yes, I have been a buyer: A couple times when I was quite young. I don't think I looked down on those women, but I did recognize that they were in a bad place. I got the impression one probably had an abusive partner. That wasn't fun and I left without "finishing."

BDF @65, I think you're right that "dated briefly" implies a couple of dates and almost certainly no sex, so "dumped" is probably not an accurate word. I really used it to exaggerate my conviction that she probably thinks very little of him.

This is all reading tea leaves, but my impression from the letter was that he's been carrying a torch for her for years and that he only sees her when they "bump" into each other (I hope this doesn't involve any stalker-ish hanging around in places he knows she's likely to be, but I wouldn't bet on it). People in that sort of situation tend to exaggerate the nature of their relationship with the object of their obsession, so I rounded down everything he said about them having a friendship and guessed (and it is just a guess) that she agreed to hang out with him a couple times, wasn't interested in him as a romantic partner, and probably finds his ongoing lust for her to make him unappealing as a friend.

So, that makes me think it is possible that she may view him more as a potential regular than as a friendship she'd want to preserve by avoiding commercial sex. That's the silver lining for the LW: Maybe selling him sexual services is exactly what she wants from their relationship.

Also, good point in response to UF about the emotional issues for men. Male customers can easily fall in love with sex workers, which can be demoralizing for the man who is in love with someone who may find him disgusting but pretends not to. It's also dangerous for the sex worker when the love-sodden customer feels betrayed.

Sex work should totally be legal, but that's mostly to reduce the risks, not because it's a great and happy career choice for a lot of people.

Quincunx @66, Ouch. And we don't even get to have sex on the job. Speaking of which I have to get back to my well-paid job that I don't especially love, which is probably why I'm goofing off here.

Ms Fan @65 - Highly appropriate and very Rumpolean - "Never have friends as clients, Fiona."

DCP @70: Aha, you're a lawyer, that explains why you wouldn't hire a goth.
And why I didn't become a lawyer.

Venn @71: Friends, absolutely. Friends were my initial client base. People I'm fucking are in a slightly different category.

If sex work is work, then of course he should ask her. How he asks, by text, email or in person should make no difference. My brother once asked a lawyer friend of his to promise to "opt out" of representing either him or his wife in their divorce.This was just fucking selfish. As a lawyer I know how difficult it can be to find clients. A divorce lawyer needs clients. A sex worker needs clients. The nature of all sorts of work is personal, but if I am a good lawyer I want to help my clients and if one of my clients is a friend, so much the better. By treating the sex worker as a different type of work we are perpetuating the idea that it is not work. Or it is not "normal" work. Real estate brokers sell houses for their neighbors. Pediatricians treat their friends' children. I trust someone more in their work if their friends use them professionally. Isn't that a sign that the person is good at their job, you know him personally and still trust that he will do a good job for you? Sure there is more at stake when your friend is also your daughter's pediatrician. More can go wrong if that job is botched than if your sex worker friend slips up (or slips out), but that doesn't mean you shouldn't trust your friend to treat your daughter, particularly if you believe she's a great pediatrician. So, the only question should be, do you think the sex worker good at his job? If the answer is yes, then hire him.