“Should I Tell Future Partners I’ve Hired Escorts in the Past?”

I’m a 20-year-old guy, and, while I think of myself as average looking, I have struggled with confidence in the past. I have used a few escorts (as well as had some sex I didn’t pay for). I treated the escorts respectfully and am not a misogynist. I used protection, felt safe before, during and after, and got tested (and was NEGATIVE); however, I deeply regret using escorts in the past.

I am trying to learn from that mistake and accept myself for who I am, and I’m ready to put this behind me. Maybe it was a good thing to get a little bit of promiscuity out of the way. I would never even think of doing it again because I believe I’m a good person. I do care about people, but, at that time, I was just foolish and horny. It’s not like I’m the first or last guy to do it (a lot of men just won’t admit doing it), but I know that’s not the point.

I learned through this that I am a relationship guy. Do you think that my sexual history has damaged my chances for a relationship? Down the road, should I tell my partner? I know I’m young and have virtually my whole life ahead of me to date other women. I try to be an honest person, but I think this might be a skeleton that will never come out of my closet. Thoughts? — Escorts in the Closet

My thoughts are that you are being too hard on yourself. So you slept with a few escorts. So what? As you said: you aren’t the first person to pay for sex and you won’t be the last person. And you know what? As long as you are disease-free and don’t have kids, your sexual history is no one’s business — not your friends, not your family, and not any future partner.

You are allowed to have past experiences that are and remain entirely yours and they don’t need to be shared with anyone. You are allowed to have a past. You’re even allowed to be glad you had certain experiences, even if they aren’t experiences you’d ever want to repeat or recommend to anyone else. Those experiences made you who you are today, and, as you said: you’re a good person.

But here’s the thing: even good people pay for sex sometimes. You can care about people and still pay for the experience of having sex you may not be able to have otherwise. Trading cash for physical intimacy isn’t a symptom of being bad. You know what is? Treating people disrespectfully. Being unkind. Being a racist or a misogynist. Blaming others for your own low self-esteem. Being close-minded. Taking, taking, taking without ever giving back. Hurting people intentionally because you’re hurting yourself and you can’t stand anyone else being happy. And people who are all of these things — even people who are “bad”— are still just human like the rest of us, making mistakes and maybe even learning from them and growing from them.

We’re all on our own journeys, celebrating our own minor and major victories and battling our own demons or insecurities or general shit that gets us down. Most of us are doing the best we can, and some of us are even pretty good at hiding the ugly stuff, the hard stuff, the stuff that keeps us from being the best versions of ourselves we can be. But we all have that stuff. All of us. Every single one of us. So… stop being so hard on yourself. Stop beating yourself up for being human and having experiences in your past you aren’t 100% proud of.

You are the sum of all of your experiences, not just isolated ones that represent a teeny tiny percentage of your entire history. You are the kindness you’ve shown others and the work you invested in reaching a goal and the moments you’ve fallen a little bit in love with someone you just met. You are the good days and the bad days and the weeks you’ve lost to being sick. You are the races you’ve won and the jobs you didn’t get and the exams you aced after too much or hardly any studying. You are all your first days of school and summer vacations and the dates you’ve had with someone you were trying to get to know. You are the sum of ALL your experiences, and you are under no obligation to share with potential partners any of the isolated experiences you feel uncomfortable with or ashamed of or that don’t effectively represent who you are now.

Don’t let a handful of experiences define your past or steer your future. Your life is so much bigger than that. And so are you.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. RedroverRedrover says:

    They should just legalize prostitution already. I’m not a big fan of it, personally, but it’s here and it’s not going away, so they might as well make it safer for the people doing it. Then guys like this won’t have to break the law if they can’t get sex through more “traditional” methods.

      1. RedroverRedrover says:

        Yes, I’ve seen that data before. But it’s not a reason to keep all prostitution illegal. I saw a great documentary a few years ago where they went around the world and studied legal prostitution businesses and which ones were safest for the prostitutes. The safest ones by far were self-owned.
        If it were legal to be a prostitute, but not legal to employ prostitutes, then it wouldn’t be as attractive to human traffickers because they wouldn’t have legal control over the prostitutes. If the prostitute themselves had to register as a business, it would be less safe for the trafficker. Another thing that would make it better is if you had to be a citizen to be a legal prostitute. That would make things much harder for traffickers.
        Also, I have to wonder if the uptick in trafficking is somewhat tied to additional awareness. When it’s legal, it’s not as underground, and so it can be tracked down more easily. Not to mention that illegal prostitution, if it involves a pimp, could be counted as sex trafficking anyway. Those prostitutes are typically not just free to go, they’re more like slaves. But they’re not counted in trafficking numbers because they weren’t necessarily brought in from another country.

      2. That’s really interesting. I had never thought of solutions like that to dissuade trafficking but increase safety for prostitutes. I agree with the must be a legal citizen and no employing prostitutes.

      3. RedroverRedrover says:

        Thanks! And the great thing about it is, if prostitution is generally legal, then you won’t end up with a black market for it, so there will be nowhere for the traffickers to go. Especially if you have large punishments for any john who uses an illegal prostitute. Who would risk it when they have legal options?

      4. Avatar photo Northern_Coast says:

        I agree with you, jlb80.
        I live in Germany, and I see lots of negative consequences of the legalisation. Huge brothels (4500 sqm) are opening in my city – and this is not a very large city. Johns come over from neighboring countries where prostitution is illegal. You can imagine what kind of clientele that is, and how they behave when they’re in the city centre.
        And the ones who are profiting from all this are not sex workers, but smug, dressed up, glorified pimps who advertise their businesses in serious political talkshows on national TV. (And if questioned what they’d do if their own daughter worked in a brothel, answer “I’d be heartbroken.”)
        Street prostitutes are everywhere, and many of them are from other countries. Are they here voluntarily? I wouldn’t bet on it. And like in the old, “illegal” times, they still have to be outside all night, going with whomever picks them up, risking abuse etc. So the dangerous half-legal milieu is still there.
        The city council can’t do a lot about it, since, let’s repeat it together: “It’s a business like any other.”
        I’m a bit more critical than Wendy regarding the LW’s question, too. In my opinion, it IS misogynist to pay an escort for sex. It’s telling that he uses the expression “USING an escort” twice. So no, it’s not okay. But it happened, and you’re not intending to do it again. Personally, I’d like to know if my boyfriend paid for sex in the past. It’s of course not something that belongs on a first date, but if you want an honest relationship, I’d say disclose this fact at some point.

      5. RedroverRedrover says:

        I agree that I wouldn’t be happy to find out that a guy I was dating paid for sex. I guess it’s an unpopular opinion judging by the other comments, but I think that in the current environment it’s immoral. The main reason being that there’s no way the john can tell if the prostitute is doing it freely, or is being coerced. They may be debt slaves or they may be actual slaves or they may be living under fear of violence if they don’t comply. Or they may be totally free to leave prostitution and they do it for the money. But there’s no way to know, unless maybe you actually know the person and know their life. Therefore if you’re paying for sex, you’re basically saying that you’re okay with taking the chance that you’re contributing to forced prostitution. You might not actually be contributing to it, but you’re willing to take the risk as long as you get sex out of it. I couldn’t date someone who thought that was okay. And if he hasn’t thought it through or realized that sex slavery was a possibility, that’s almost worse. It just shows he doesn’t even think about what their situation might be like or why they would agree to prostitute themselves.
        It’s too bad that legal prostitution has gone so wrong in Germany. I hope that instead of fuelling the movement to keep it illegal, it can be used as a case study to learn the right way to do it. In my opinion, if the safety of the prostitutes is the core of the legislation, it will become difficult to take advantage of them. If no one was allowed to make money from prostitution except the prostitutes themselves, then traffickers would have a real problem doing business. So would the sleazebags who run those brothels.

      6. There will always be sex trafficking because some things will always (rightfully) be illegal: kidnapping/bait and switch, sex with minors, etc. Legalizing prostitution will chip away at some of the issues if more countries get on board. But as long as it is illegal somewhere, then it will behoove criminals to abduct women and children from that place for criminal activities.

  2. LW, I really think this should stay in the closet. Not because it’s something you need to feel ashamed of (it isn’t), but because it’s unnecessary information.
    I don’t need to know every detail of every sexual encounter my boyfriend has had in the past, and this counts as one of those details. I do know that he had some one night stands in college; that was many years ago and I couldn’t care less. It has zero relevance to the relationship that he and I have.
    You were careful and safe and got tested, you know there’s no chance of your passing on an STD, so these encounters have no relevance to your future relationships, either. 🙂

  3. WWS — I am not even going to try to add to that.

    (Wonderfully written, BTW!)

    1. Yes! Wendy´s reply was beautiful

  4. WWS for sure – she really says it perfectly. My fiance and I are very open with each other, but we have never shared any specific details about our sexual pasts, including numbers of how many we’ve slept with and it has done no damage to our relationship. As you say, this is part of your past, so leave it there and move onto the next phase of your life!

  5. That was a super heartfelt response, Wendy. I loved it.
    LW, a lot of people judge others a lot of the time. ESPECIALLY when it comes to sex (and parenting and being single and weddings and your hair color, but I digress). That’s why I don’t think I would advertise your sexual past with potential partners. It’s nothing to be ashamed of at all, and Wendy covered the reasons why. Personally, I don’t care about a boyfriend’s sexual past and I probably wouldn’t continue seeing someone if he cared that much about mine. It’s just like, so what? You know?

  6. WWS. This is so not a big deal. And, if it is to somebody you’re seeing, then that’s not the right person for you! It’s okay that you did this. Hell, I’ve done things I’m not proud of. Probably will again. Nobody is perfect. And anyone who is, is lying (and really boring – seriously, our flaws are what make us interesting).

  7. You would only need to tell someone if you had an std and even then you would say I have x rather than I have x because I slept with prostitutes. There’s really no reason to tell anyone about it nor is there a reason to be ashamed but its just better not to tell.

  8. Wendy, I’ve always enjoyed your writing but I feel lately like you’ve reached a new level – such beautiful and compassionate, well-written responses. This was no exception. Keep up the great work 🙂

    As for LW, definitely WWS!

  9. Anonymous says:

    I have a checkered past too – to the point that I disclosed to my partners that I have tested positive for Hep B. Disclosing potential STD exposure is common courtesy and one has an obligation to do that. Yet disclosing shadows of a past, yet varied sexual history? That depends on the person you’re seeing and how much you trust them. One guy I was seeing did reveal to me that, although he did not have as many partners as I did, he HAS paid for sex before. Yet even though some people may make a revelation of that kind a red flag, I also saw how kind he was now, how I appreciated his honesty and how dedicated he could be, as well as all the other bells and whistles that signaled to me I could be serious with him. Almost 10 years later (including 7 years of marriage), I’m still seeing that guy. And I’m sure something similar will be happening to you too….Good Luck LW.

  10. Avatar photo fast eddie says:

    Way, way too much energy on such a tiny part of your life, no pun intended. I lost my virginity with a professional sex worker in Athens Greece (it’s legal there) and the only regret I have is that happened far too fast. It was not the last time that I hired a woman for sex but it didn’t take very long to conclude that masturbation was just as satisfying, safer and cheaper but sometimes a hard cock overrules reason. As long as you use protection and get tested before having sex with someone else there’s nothing wrong with paying direct. Telling a partner all about your sexual history is something that listening to your gut about is the best advise. The best general guide I can suggest is to not say anything until your pretty sure that the relationship is going to be long term.

    I bet this subject will kick off a lot of comments.

    1. That’s actually fascinating!! And isn’t it kind of a rule that most first encounters are over way too fast and/or fairly unsatisfying??

  11. Hmmm so I once worked as a stripper and I take this kind of information similarly. I’ve always told partners because I don’t feel bad about it at all. So I agree that you should stop beating yourself up about paying for sex. It’s not a big deal. There are lots of sex workers and someone is hiring them, yet that side never gets talked about. I don’t think it’s wrong per se not to mention it to a partner, but I also don’t see the point in hiding it. The right person wouldn’t judge you or care that you paid for sex. My husband was a very late bloomer and told me he considered paying for sex so he could lose his virginity. He didn’t do it, but it wouldn’t have mattered to me if he did. So I wouldn’t go telling everyone if I were you, but I also couldn’t imagine not eventually telling the person I will my spend my life with.

    1. That’s what I was thinking. Don’t go around broadcasting it, but don’t hide it either.

    2. And also I just want to add, that I think it’s important to tell a lifelong partner eventually to help get rid of the stigma. Because again the right person won’t care. Everyday people pay for sex. The more people who can talk about it openly, the less stigma there is. There are many countries where paying for sex doesn’t have the negativity it does here.

  12. I’ll be the first naysayer: this letter gave me the creeps. Not the escort thing, but the language and tone. “Used escorts” =/= (to me) someone who recognizes those women as people. “Maybe it was a good thing to get a little bit of promiscuity out of the way”–the word “promiscuity” rubs me the wrong way; it’s a judgmental word. As Wendy says, paying for sex doesn’t automatically equal “bad person”. And why is he careful to mention that he hasn’t always had to pay for it? He’s learned he’s a “relationship person”, great. But when he meets women who are interested in a relationship with him, is he going to be as generous with THEIR sexual pasts or see them as “bad people” if they’ve engaged in behavior he doesn’t approve of?

    To me all this sounds suspiciously like Men’s Rights Awareness Activist stuff, though it may just be standard Nice Guy stuff. In any case: LW, if that *isn’t* you, I would think about how you present yourself to women, because this would scare some of us off.

    1. Wendy (not Wendy) says:

      (sorry, that was me–obviously not Wendy herself.)

    2. Hi, I’m the guy who posted. I understand how my tone may have been weird. I get that these escorts are people too, that’s the point I’m trying to make! Also, I’m sorry it offended you about clarifying I haven’t always had to “pay for it”. I just felt that someone was going to assume that’s the only kind of sex I’ve had. One last thing, I would never hold anyone’s past against them. Particularly people I like. People change and grow from experiences and mistakes. I don’t present myself in any weird way. I’ve just had low self esteem in the past. I try to be a nice friendly guy. It isn’t me anymore honestly. I know that it’s difficult for someone to understand someone’s tone over a letter, and I’m not being sarcastic. Thanks for the kind words everyone! I’m glad most people on here are very forgiving and open minded.

      1. Wendy (not Wendy) says:

        I don’t think you’re getting my point–in my opinion (and apparently some others), you ARE presenting yourself in a “weird way”–at least through this letter. The only reason I commented on it was because I thought there was a chance that you are a good, regular guy not realizing how he sounded. I’m not offended. And I am, to some extent, “forgiving” and open minded. (I put “forgiving” in quotation marks because you haven’t done anything that I need to forgive you for.) The way I read your letter just made you come off as creepy. Again, it isn’t the behavior. It’s that you sounded defensive and judgmental. This, for instance: “I just felt that someone was going to assume that’s the only kind of sex I’ve had”–why would we care? Why would that matter in the context of your letter? You say you realize that “escorts are people too”, so make sure your words reflect the way you feel.

  13. I think this is NBD *because* you used protection, therefore basically ensuring you, your partner/escort, and all future partners you and the escort have are safer. I would feel otherwise if you had unprotected sex with them (my ex-bf hired an escort after we dated and paid extra for BBFS – meaning, unprotected and not pulling out. *That* I judge.)

  14. SixtyFour says:

    I think you should disclose this information to your future girlfriends. It’s not a big deal, and it’s not something you should be ashamed of, but it seems like it’s a really big deal to you. You don’t want to always fear that this might come out later, and you don’t want to end up lying about it because you’re ashamed.
    Don’t sit your girlfriend down and have a Serious Talk with her and break this info to her like it’s something huge, but after you’ve been dating for a while and if/when the opportunity presents itself, like while watching Law and Order SVU or Pretty Woman, just mention that you frequented escorts when you were young but don’t do it anymore. And if she is curious about it, describe all the things you wrote here. If she runs, then she’s not someone you want to be with anyway.

  15. LW, I would say to give yourself a break. My husband and I have been together 10 years and both know that we were by no means virgins when we got married. We have talked about it from time to time but never really delved into the details. Let sleeping dogs lie and I will tell you that when you get distance from this, it will be less of a big deal.

    Now, that being said, I liked what Wendy (Not Wendy) said about the language you are using. There is a bunch of shame and judgment in your letter. Be open minded about the totality of your sex life and be kind to any future female partners and their histories.

  16. Jamielynn says:

    I say good for you. I wish it were as easy for girls to be able to pay for sex, because god knows I would have gone for it a long time ago. Long story short, I grew up terribly bullied and never developed enough confidence to interact with the opposite sex. I thought it would get better over the years, I’ve gone to therapy, etc., but this feeling that I’m gross and no one will ever want me still lingers.

    Now I’m 33 and I have absolutely no relationship experience. The only sexual experience I’ve ever had is a handful of one night stands in college. Now I’m so afraid to even try dating because of my lack of experience across the board. I don’t know how to explain that to a potential partner. Now I’m at an age where guys don’t want to go to bed with a woman who really doesn’t know what she’s doing.

    So once again I say good for you for getting some experience. This really is no one’s damn business.

  17. LW, if I was dating you, I wouldn’t want to know that you paid for sex as a horny teenager. It’s not that I think it makes you a bad person (it totally doesn’t), I just don’t want to have to think about it. I guess it all depends on the girl that you’re doting. If they start bringing up past sexual partners, and ask you about yours, then, yeah, tell them. If they fault you for what you did in your past instead of looking at who you are now, good riddance to them. But I wouldn’t bring it up otherwise.

    1. So, my ex-fiance breast fed until he was four. His family jokes about it. BUT, it totally skeeved me out. I don’t know why. It just did. So yeah, I don’t judge him for it, but it was something I couldn’t get out of my head. The boob area ended up being off limits. That was totally my hang up, I realize that.
      Unless asked, there are some things I just wouldn’t bring up. But I’m not the kind of person that thinks you NEED TO KNOW EVERYTHING about your partner or friends or family.

  18. Everyone approaches relationships differently- I think with an issue like this it’s not about right vs. wrong but rather a subjective preference. Some tell their partners EVERYTHING and would consider it a lie by omission if you didn’t disclose this. Others their sex lives none of their partner’s business, so long as it’s not still happening and doesn’t affect them. You just need to figure out what level of disclosure you and your are comfortable with. If you want to know more about how your girlfriend views this topic, maybe broach a hypothetical with her, or even ask her flat out how she feels about partners sharing their pasts.

  19. tbrucemom says:

    I remember asking my now husband if he ever paid for sex and he said no. I wasn’t being judgey at all, just curious, we’re very open about our past sexual experiences. He said no. The funny part is the very next day he was telling me a story about vacationing in Brazil and that he hired a female local to show him around, have dinner with, and yes had sex with! I guess in his reasoning either because it was in another country where it was legal or because it was a “package” deal he didn’t think he paid for sex.

  20. I think you should tell your girlfriends/serious partners. For some people, it’s a deal-breaker, and they’re entitled to that kind of information if they ask for it or if you reasonably perceive that it would be important to them. I’m apparently in the minority on this, but I definitely think it’s relevant information that goes to character. Everyone has character flaws–don’t get me wrong–but everyone deserves to know the values of their serious partner. Just casually mention it when things get serious and see where it goes. For most people, I’m sure it won’t be a problem.

  21. Avatar photo something random says:

    If I’m being honest, twenty-year-old (very cautious) me would have been skeeved out if I guy I started to date told me his first few times were with escorts. I don’t think it would bother me now, but I think a lot of young adults who are just becoming experienced might have a less worldly reaction. Of course now is a different time and so maybe that isn’t the case. I would just avoid bringing it up early on. It really is nobody else’s business. But know that it doesn’t make you a bad person.

    This is going to be unpopular but I’m just going to say it. While I don’t believe people’s morality and sexuality are intertwined, I wouldn’t want somebody I loved to go into the sex industry. And would probably discourage someone I loved from turning to the sex industry to gain their first few experiences.

    I know there are exceptions. There are women (and men) who work phone lines, webcams, strip, or escort that are young and comfortable with their bodies and what they do. Maybe they feel empowered and like they make good money in a way that is fun and giving. But for every one of these young people, worldwide there are probably about 10 or more people that have been coerced into using their bodies in ways that feel degrading and hurtful. So many of these people got started as children or underaged teenagers that were often forced by their very parents to help feed their families. They are being deprived an opportunity to develop themselves in other ways.

    Even in the united states, many young people who have run away from home wind up in sex industries for lack of other options. And in my area, glamourous young escorts aren’t the norm. A lot of local prostitutes (don’t ask how I know) struggle with addiction problems. They aren’t educated, have crappy self-esteem, and are doing the only thing that seems accessible. The men who visit them tend to be married and often are suffering from sexual compulsions.

    The oldest profession isn’t going anywhere and criminalizing it instead of managing it might feed the exploitative nature. And there are certainly exceptions where paying for sex makes sense (I’ve heard of this in situations with disabilities). I’m glad the stigma around sex toys, therapy, and entertainment is receding. Nobody’s personal value should be associated with how they use and experience their own body. But if we are going to discuss sex work its only fair to examine it from all angles.

    Let the throwback begin!

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