My Boyfriend Has a History of Sleeping with Prostitutes. What Should I Do?

I met a man online last year who has treated me wonderfully. He is everything my ex’s have not been. He treats my child as his own. He is transparent (opens all accounts, phones, computers), honest, loyal, caring.

After one month of dating, he told me that he slept with prostitutes for several years. He’s in the military and started with them as a virgin at 23 and continued until 28. He’s seen around 20-30. He is 30 now (like me). He let me read his journal from those years. He never wrote about what they look like or the intercourse, so I don’t think he was focused on “using them” but instead he wrote about how desperate he was to find someone to love and to settle down. He even tried to date them. He had a very hard time dating and was rejected often. He is a very sensitive man. I can tell that he was looking for a connection, love, and intimacy. He also wanted to get laid and that was an easy way to do it. He believed that it was more respectful to pay a woman for the act instead of randomly hooking up with someone at a bar. However, he was arrested at 23 for it and still saw them for years after that. That alarms me. He feels regret and remorse but I just can’t get past it. It doesn’t bother me all of the time, but it comes up from time to time and I feel worried that I’m making a mistake. Especially since I’ve been through a bad marriage. I don’t think he is a sex addict like my ex; sex with him is very vanilla. He seems more interested in the connection for the most part.

Recently he flies to my hometown to ask my father for my hand in marriage and now he just proposed to me. I love him but I just feel worried sometimes, I am afraid of his past.

Like I said, he is wonderful to me and outside of this, he’s pretty perfect for me and my child but I worry I am making a mistake. What do you think? Should I let his past go? Is it a big red flag?


Somehow, in ten years of writing this blog, I’ve never gotten this question and I’m really glad it was worded the way you worded it. It forces me to think about my answer and try to put myself in your boyfriend’s shoes.

To be fair, it’s a little tricky because I’ve never been to a prostitute. It’s not that I never thought about it. I’d see thousands of ads in the back of LA Weekly and marvel at HOW MANY GUYS were willing to pay for sex. Personally, I couldn’t fathom it – both because I had no money in my twenties and because half the fun of sex was in the act of seduction. Paying someone to be interested in me for an hour was far less interesting than charming someone into actually being interested in me.

But that’s not who your boyfriend is. He’s not a player. He’s a sensitive man with no game who was willing to take the easy way out and straight-up pay for sex. I can’t say I have any friends who’ve confessed to being this way, but I make it a policy to try not to be judgmental about different people’s life choices. Especially if they’re not hurting anybody else. And that, to me, is what makes your boyfriend’s story feel more sweet than creepy.

I think you should let his past go and focus on how he treats you and how you feel with him

While most men would never bring their sordid past up at all, and if they did, they’d minimize it, your boyfriend told you the whole story, his feelings about why he did what he did, AND shared you his journals from the time. You tell me he was looking for connection and that was the best he could do? I completely believe him.

Furthermore, I believe that (most) people grow and change a lot from 20 to 30, and again, from 30 to 40. I wouldn’t want to be judged for the most embarrassing behavior from my early twenties, and I don’t suppose any of our readers would want to either.

So, as surprised as I am to be saying this, I think you should let his past go and focus on how he treats you and how you feel with him, as opposed to behaviors he was open about a decade ago, well before he met you.

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  1. 1

    I completely agree. None of the things that would be red flags (for me) are present in this story: no lying, no secretiveness, no indication it’s ongoing. If he had been a “sugar daddy” and supported his various girlfriends financially, would you have even though to be concerned? I really hope you don’t hold his past against him, especially not when it sounds like he is doing everything in his power to demonstrate his commitment and respect for you.

  2. 2

    Why shackle yourself to a guy with a criminal record, someone who didn’t learn from their mistakes?   If the law didn’t stop him, what makes you think you can when he runs into the arms of a hooker for comfort after you had a fight.

    Date him sure, but marrying him without a very very long engagement is setting yourself up for a fall.  Be smart, protect yourself, your finances and your health.  If he pushes for marriage then you have a very insecure guy on your hands who is desperate to marry anyone. Why settle for that?

  3. 3

    To Dani-  I completely agree with EMK. The fact your guy has been very transparent with you speaks volumes of his character. He hasn’t tried to hide his past from you, and that had to be a difficult decision for him to tell you about the prostitutes. He’s being an open book with you, as it should be. If he’s that honest now, he’ll continue to be truthful. From the sounds of it, he treats you like a queen and also loves your child. That is a good, solid man.

    Don’t let his past determine your future with him. He clearly matured and has left his youthful experimentation behind him. I’m a middle-aged woman and see too many men in my demographic who are emotionally still boys.

    You found a decent man who wants to take care of you and build a life with you. That is priceless. Don’t let him go. All the best to you—


  4. 4
    Emily the original

    I’m not sure why he revealed this to her. Fine, he was bad with women in his 20s and wanted connection. I’m sure there are other men in his shoes. But now she has the images of him with prostitutes in her mind. She may understand his reasons as a person but as a woman is borderline creeped out. Also, there’s desperation in this story, which as a woman kills some of the respect she needs for him as a man for there to be attraction. No woman wants to hear her man has no game at all, just as no woman wants to hear he hooked up with half the women in his college. TMI. If he’s now a different person all these years later, why bring up a person who no longer exits?

    1. 4.1

      I’ve had this experience with an ex.  He told me when we had the condom discussion.  He had always used a condom but I’m glad I knew.  A man with history with prostitutes is a higher risk category for me.  Then there is the fact that he didn’t want to get tested  . . . a tale for another day.

      I’m fine and have tested clean since.  I think his not getting tested bothered me more than the prostitutes.   He was a woefully disorganized person, I must admit.  If I arranged for the whole testing situation he would have shown up and done it but I refused to organize that for him.  And he was a bit immature about women.  One thing I can say is while hookers provide sex, it doesn’t mean the man learns much about courtship and seduction from them.

      He was really, really sweet.  Again, I’m glad I knew.  Then it made sense that he was sexually experienced but not as experienced with kissing.  (Quick study, though. ;-)) That’s the thing to. Going to a prostitute doesn’t make a man a good lover.  Or knowledgeable about a woman’s pleasure.

      It meant a lot to him to be able to be vulnerable, tell me the truth, and have me hold that without judgment.  Really set a tone of openness and honesty in our relationship.  And yes, you know me and my former history of beta males.  So that didn’t affect my respect for him, but him not taking some responsibility (getting tested, buying condoms) eventually did.

      On a side note:  that was my last beta male. I have been finding men in the middle lately and it certainly is  . . . interesting.

      1. 4.1.1
        Emily, the original


        It meant a lot to him to be able to be vulnerable, tell me the truth, and have me hold that without judgment. 

        I just wouldn’t want to know that a man I was dating seriously had been with a prostitute. It’s one things to say, ” I didn’t do well with women when I was younger.” Ok, fine. But I don’t need to know every detail, that you could never get a date or get laid … because the natural response is … why am I hanging out with this guy?

        On a side note:  that was my last beta male. I have been finding men in the middle lately and it certainly is  . . . interesting.

        What are the dudes in the middle like?

        1. S.

          I guess we differ. I want to know details, especially if it possibly affects my sexual health.  Now, he didn’t tell me specifics.  But yeah, a lot of men I dated weren’t the most successful with women.  I don’t mind that.  They were very sweet, wonderful men just no where on the alpha scale if that exists.

          why am I hanging out with this guy?

          I’m hanging with this guy because he’s kind, treats me well, looks hot to me, and has no trace of arrogance.  That’s how I roll. 😉  Still is even with middles.

          First, middles I meet in person.  They are not online and are rare anyway.  It’s interesting.  Sometimes there is a bit of a power play.  They want to lead and it’s usually not where I want to be led.  (Not talking about sex.)  So they are strong.  It’s not edgy, it’s just strength.  But they are all of the above too.  It’s actually really attractive to have both rolled into one.

          My default was feeling safe.  If I guy made me feel safe by being kind, and we could have vulnerable talks together, and I found his face/body hotter than a firecracker, I was in.  Alpha males–just to use that term for ease, not that I agree with the term–just don’t make me feel safe.  I always feel they are going to make fun of me, be full of themselves, or just be unkind.  I’m a sensitive person so I’m not a match with them.  They probably are good men too, but once I feel like someone might say something unkind any budding attraction I may have had dies a quick death. Others are less sensitive to that kind of thing and can remain attracted.

          Middle have a combination of both.  But I have to be careful too because they even sometimes have conflict over which they are sometimes.

          Still learning. 😉


        2. Emily, the original


          I want to know details, especially if it possibly affects my sexual health.

          I could see that. I hadn’t thought of that. But, really, someone could give you something even if he’d been with just one woman. I guess the best thing to do is be safe until you both get tested.

          My default was feeling safe

          Well, a little safe is good. Not too safe.  🙂 I’ll have to think more about your concept of the middles. Just off the top of my head, I don’t know any.

  5. 5

    As one of those rare people who doesn’t see sex as a big deal, I don’t see how visiting a sex worker prior to the relationship is something that should end a relationship.  If anything,  knowing how bad people tend to be in bed, I’d be feeling sorry those poor women had to put up with that for any amount of money 😂

    I’m friends with a woman who did cam work for a few years. She’s in a similar situation regarding her kid,but she doesn’t have access to child care (in the way of family). I remember sitting at her home one night and I offhandedly asked her how work was and she replies “I feel like I’m chatting more than showing my tits.”. This seems to be a common thing sex workers tell me. A lot more talking than screwing apparently.

  6. 6

    What is this giant hang up about prostitutes?  Yes, I wouldn’t ever do it.  Yes, I find it distasteful.  But in this new world where people are free to do what they want and sleep with whom they want, what is the big deal?  Would you be having the same misgivings if he admitted to one night stands?

    1. 6.1

      Honest question, Skaramouche, would you mind if a woman had a history of seeing male escorts (including criminal history)?

      1. 6.1.1


        98% of women will never have to see a male escort due to the market saturation caused by men seeking casual sex, so that’s really an unfair hypothetical. But honestly, if she did it in her 20s and was over it, no, it honestly wouldn’t bother me.

        1. Marika

          Hahaha, fair enough Shaukat.

        2. Yet Another Guy


          Once again, you have highlighted the fact that female incel is an oxymoron.   A lot of women try to shift the argument to not being able to have sex with a man they desire; however, that is little more than a straw man.  There are very few woman on this planet who cannot find a sex partner if they desire one.

          With that being said, visiting a sex worker is fairly common in the military services.  All one needs to do is visit a military base and one will have one’s answer.   Men outnumber women by a ginormous margin, and the bulk of the men serving in uniform are under 26 years old.

  7. 7

    Showing his diary about the sex workers is creepy and TMI.

    I feel like there’s more to this story.

  8. 8

    Here in Europe prostitution is legal and I do know a number of decent guys who paid for sex when they were single. Personally, I wouldn‘t „punish“ him for his honesty and let this subject go. Good luck to you.

  9. 9
    Elle 1

    She uses words to describe her feelings that raise red flags for me. She feels worried and alarmed enough to write to Evan, despite the fact that she has only positive things to say about this man aside from his sexual history. On the one hand I agree with Evan, but on the other hand her intuition may be telling her through these feelings not to marry this man. I trust intuition more than logic and reason in these circumstances. Marriage is about feeling secure in a committed relationship. If she isn’t feeling secure now, she probably never will. For that reason, I think she should move on.

  10. 10

    I enjoyed reading Evan’s response, and agree with all of it.  The guy is described as someone who was simply looking for a connection, through sex. For that matter, he seems to be one who creates emotional bonds through sex. I think that’s more rare for men compared to women.

    That being said, EMK.. the following part of your response was a bit cold!

    But that’s not who your boyfriend is. He’s not a player. He’s a sensitive man with no game who was willing to take the easy way out and straight-up pay for sex.

    C’mon Evan.. that’s just.. look.. you surely realize that confidence and game is a positive feedback loop.  If a young man has the physical tools, he will experience so many instances where women affirm his worth as a partner, for minimal effort expended.  And if said guy has even a modicum of intelligence, he can easily build upon it.

    I think the guy described in the OP does not have those advantages, and if he is sensitive (which is something to which I can relate), then he likely internalized every rejection, and associated it with self-worth.  I’m sure you’ve seen this a million times in your travails as a dating coach.  So, to say he “took the easy way out” is just too harsh.  Going against what society, or at least women in the dating realm, says about your worth as a partner, and building confidence in the face of such negativity is difficult.

    1. 10.1
      Evan Marc Katz

      I can sympathize with a sensitive man with no game who was willing to take the easy way out and straight-up pay for sex. But that doesn’t negate my belief that this is exactly what happened. You may be lonely, you may be shy, you may be insecure, but you’re not “brave” for paying for a hooker in the face of “society.”

      1. 10.1.1
        Karl R


        I think you misunderstood what Scooter said.  He didn’t say that hiring a hooker was brave.  He said that having confidence, especially when society is dumping on you, is difficult.

        1. Evan Marc Katz

          If that’s the case, then I stand corrected. It wasn’t clear to me from his last paragraph. Either way, as a coach I’m sympathetic to anyone who is struggling, but as you and I know, the one thing you can change is how you approach things; you can’t change the rest of the world.

        2. Scooter

          Karl had it spot on.  I didn’t say going to a hooker is brave, however, it’s understandable under such circumstances.

  11. 11
    agatha schwarz

    I think the LW is not so much in love with him. I wouldn’t marry a guy who goes to my parents for my hand before speaking of it with me, after a year of dating. He is desperate, he has issues, and to show his diary about his past prostitutes: ick! I would run, not so much about the hookers – though I despise the behaviour – but because of his actual behavior with you. Too dependant, too creepy.

    1. 11.1
      Karl R

      agatha schwarz said:

      “I wouldn’t marry a guy who goes to my parents for my hand before speaking of it with me,”

      That’s a cultural (and sometimes generational) thing.  My wife was a little disappointed that I didn’t ask her father’s permission before asking her to marry me.


      It never occurred to me.  I wasn’t marrying him.

  12. 12

    What is with the quote “especially if they are not hurting anyone else”. Anyone who is paying to use another persons body may want to think about this a bit. If prostitution truly isn’t hurting anyone, then why are prostitutes disproportionately coming from impoverished backgrounds? Why are their trafficked women at all? Why is this not the sort of “work” that people aspire to? I am not saying that happy escorts do not exist, BUT for the majority, it is not something that they want to do and it is usually done by people with no other options. Have you ever sat in the middle of a place full of men, with paid women who look like they want to be in any place other than where they are? No, sorry, I have traveled through many poor countries where westerners go in order to enjoy paying for women, and it is not a happy atmosphere.

    1. 12.1
      Karl R


      I watched this TED Talk a few weeks ago.  I believe it answers all of your questions:

  13. 13

    I cannot believe anyone is encouraging her to continue seeing this man. Just because “he’s vanilla” in bed with her doesn’t mean A THING about whether or not he’s got a sex addiction problem. The guy was arrested for soliciting a prostitute, yet continued to break the law, risk his health and risk serving more jail time by paying for sex again after the arrest. One of the key signs of addiction is when a person continues to do something despite the negative consequences it has in their life. If this dude doesn’t see going to jail as a hugely negative, destructive event in his life… if that wasn’t a huge wake up call to him, that would be a huge red flag to me. Yes, it might have happened a long time ago, but I wouldn’t trust a man like this unless he was in therapy and/or had done some major work on himself around the issue. Even then, I’d tread carefully.

    Secondly, she stated that she doesn’t think this guy is a sex addict like her ex…. so she has a history of dating men with sexual addiction, and this seems to be a pattern for her. If I were her, I would RUN to a 12 step meeting like COSA (co-dependents of sex addicts). This is more about HER past with sex addicts than it is about whether or not this guy is a suitable partner. Good luck to the OP, but again, my advice is to RUN to therapy and/or a meeting.

  14. 14

    I cannot believe anyone is encouraging her to continue seeing this man. She has a history of dating sex addicts…. HELLOOOO?!?!? First red flag. Next, he got arrested and STILL continued to risk his health and the threat of more jail time by continuing to solicit prostitutes??!?!?!? BOY BYE!!!! One of the biggest indicators of addiction is when a person continues a behavior despite major negative consequences to their health, job, life, etc. If being arrested didn’t come as a wake up call and enough of a reason to STOP paying for sex, I don’t know what it would take for this guy to see the writing on the wall and face this problem for what it is. Another arrest? An STD? RUN, don’t walk away from this guy. And go to a 12 step meeting like COSA (co-dependents of sex addicts) and/or therapy while you’re at it.

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