“I’m Married, But I’ve Fallen In Love With an Escort”

I have been married for 28 years but the love is dead. I have been having an affair for two years and am madly in love with this woman and she with me. We were making plans on one day getting married after my divorce. I have been going to school full-time along with working full-time to prepare to provide for her and myself. I met this woman as an escort (I am not proud of that but it’s the truth). We hit it off immediately, and I persuaded her to stop doing what she was doing and I eventually got her enrolled in a medical assistant school, which she loves.

Recently I found a hidden app on her phone for text messages. I confronted her about several texts yesterday. After a long, drawn-out discussion I found out she has had several affairs. One affair is with a guy who has been giving her money for her services. She has plotted on so many occasions to hook up with this guy around my schedule. My heart is crushed, but I still love her. She’s begging me not to leave her. I know I should leave but can’t find the strength to do so. She makes me so happy. But now I’m torn in two.

Please give me some advice. — In Love with an Escort

Why aren’t you divorced yet? If the love is dead after 28 years of marriage and you’ve been having an affair for two years with a woman you’re madly in love with and plan to marry, why haven’t you divorced your wife yet? You don’t mention that you’ve filed for divorce, so I’m assuming you haven’t. Does your wife even know about your affair? Does she know you plan to marry someone else? Does your wife know that the reason you’re going to school full-time (on top of working full-time) is in preparation of supporting another woman? These are all things that should be addressed immediately before you shift your focus onto your girlfriend/mistress. Deal with the wife you’ve got before you start supporting (or planning to support) the wife you want.

Ok, so you want to marry your girlfriend — once you get divorced — and you’re concerned that she’s been having affairs behind your back. Well, first of all, she’s an escort and, even if you believe you “persuaded her to stop doing what she was doing,” if she’s accepting money from a man in exchange for her company (and maybe sex?), then she’s still doing what she was doing. She may be enrolled in medical assistant school, but girlfriend still needs to pay the rent and, if she’s paid well doing what it is she does, it’s probably going to take a whole lot more than some persuading from a married man who isn’t supporting her to get her to stop.

If you want to be with this woman — and again, I am not endorsing your being with her until you actually separate from your wife — you have to accept that she shares her company (and her body?) with other men for money and that that kind of work — that kind of money — is very, very hard to walk away from. She might tell you she’s ready to quit, but that’s like an alcoholic saying he or she is ready to stop drinking. Just because they say it, doesn’t mean it’s true. And even if it’s true, it doesn’t mean there won’t be relapses and it won’t be a struggle to quit for good. She has to WANT to really give it up, and she has to believe that her life without that job is better than it is with it. Something tells me that the life of a student with a married boyfriend on the side, who apparently isn’t in a position to support her, isn’t tempting enough to walk away from the $$$. And, as long as she is working as an escort — and maybe long after–her boundaries, or the ways she defines what is ok and what isn’t ok when it comes to intimacy with people outside her relationship, are going to be pretty fuzzy.

Bottom line: this woman isn’t like other women you’ve probably dated. She’s an escort. She plays by different rules. And since you’re the kind of guy who hasn’t respected generally-accepted rules of relationships (like, don’t cheat on your partner), this might be a good match for you. If you can both accept that neither of you is a rules-following kind of person, and if you give each other plenty of leniency to conduct yourselves however you want, and if you practice very safe sex (and get tested regularly), and if you don’t try to change each other, maybe you can actually be happy together. But, if you can only be happy with this woman if she quits her job and does the kind of work you choose for her and if she has to be 100% faithful to you (however you define “faithful,” and not necessarily how she defines “faithful”), then she’s probably not going to make you happy in the long run (and now you’re getting a small taste of what the misery of betrayal could feel like long-term).

Regardless of what happens with the mistress, the first thing you need to do is end the marriage you already checked out of years ago. Your wife of 28 years deserves some honesty (and the chance to find her own happiness, not to mention get tested for any STDs you may have exposed her to).


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


  1. You don’t even have the decency to divorce your wife before getting involved with this other woman?? That’s horrible. Seriously horrible. Even if the love is “dead” as you say, it’s still the decent thing to do! A decent human being would break it off before getting involved with someone else, especially with a WIFE he’s been with for 28 YEARS.
    I have to say though, I’m pretty sure this woman is using you LW. You’re in love with the *idea* of her. I really don’t think you’re actually in love with her. The crazy chemistry is apparently there and the difference between that and your marriage is night and day. You got her into school and then you found out that she’s hiding the fact that she’s still an escort from you. Although I can’t say I feel bad for you because I don’t. I feel REALLY bad for your wife who may still think that her husband is committed and loyal to her. That’s shitty.
    I hope you have the decency to divorce your wife and break it off with the escort girl. Or don’t. It seems you two deserve each other.

    1. simonthegrey says:

      Don’t you wonder how many others of her paid boyfriends she has had the same connection to and the same chemistry? I’m not shaming her – if the money is good, and she’s doing this because she is ok with it and not because someone forced her into it, then more power to her – but my guess is that if more than one guy is willing to believe in an instant connection, and is willing to pay for it, it’s human nature to take.

      1. Exactly. That was what I was hinting at — this girl is paid to have chemistry with guys. He’s in love with that chemistry which they supposedly have, but it definitely sounds like she’s good at convincing lots of guys they have it too. If the marriage truly is “loveless” he’s going to eat that right up, especially when she talks about building a life together…

      2. I’m so mad at him for the wife. He didn’t even mention her besides trying to rationalize being with his escort because the love is “dead”. If it’s truly dead, then man up and divorce her!! Gah, so angry.

      3. I think this was an episode of Law & Order! I can’t remember if it was regular L&O or SVU… anyway, an escort kept convincing men that they were in love and to leave their wives and support her while she goes thru school and “gets out of the escort business (which she’s only doing to put herself thru school!!).” Then she dumps him when she meets a richer man, since she’s still doing her thang. Wash, rinse, repeat… Eventually someone ends up dead, since it’s Law & Order.

  2. So, I’m just going to be blunt, LW: You’re a fool. You’ve convinced yourself that a woman whose job is to … befriend … men for money – which is how you met her, no less! – is going to quit doing all of that to eventually marry a still-married man who is likely at least a couple of decades her senior and be a medical assistant. Dude, this isn’t Pretty Woman. You’re not Richard Gere swooping in to save a poor victim of circumstance. Your girlfriend (“girlfriend?”) chose a lifestyle that makes her a lot of money and she seems pretty content doing what she’s doing for a living, since she hasn’t given it up, and I wouldn’t look for her to do so in the near future. You’re a client. Presumably a generous one and one she’d like to keep, but still a client. But that’s your problem. My only advice to you is to divorce your wife, pronto. She deserves better than to be married to man who has been running around on her for two years and is in love with an escort that he plans to marry as soon as he gets through getting the education his current wife is likely helping to support him to get in some capacity. I hope she gets a great divorce lawyer.

    1. Ha ha

      “befriend” – is that what the kids are calling it these days?! 🙂

      1. It’s kind of like “hanging out”.

  3. I’m not even going to comment on the fact that you are cheating on your wife. That is disgusting, and I’ll stop there. You say your “girlfriend” begs you not to leave her? Do you take this as a sign of her love for you? Here’s an alternate theory: you’re a meal ticket, probably one of many. You need to divorce your wife if that’s what you want, and then you’d be free to date other people. But I would take a long look at yourself and figure out why you chose to cheat rather than divorce. (And by the way, do you really think that a woman who knowingly dates a married man will be faithful to you? Her boundaries are a bit fuzzy and I don’t think it’s entirely because of her profession.)

  4. Stonegypsy says:

    argh, so much facepalm in this letter.
    Seriously, I’m with everyone else in the “feeling awful for your wife because she’s married to such a tool”
    I’m also just completely appalled by the double standards that you seem to be taking as a given here. You’re married, you’ve been having an affair with this girl for 2 years (and you met her as an escort, so we can go ahead and assume you were cheating long before that), but you are shocked, SHOCKED that she is continuing to support herself in a way that “betrays” you, the married man.
    You’re… I have nothing nice to say here. Divorce your wife, maybe just stop being in relationships altogether because you suck at this.

  5. Lily in NYC says:

    I can’t put my finger on why, but I get the feeling this one is a fake.

  6. 2 year long affair. Your wife is either complicit in this or you are an extremely good liar. It might do you some good to realize that the things you’re feeling now, your wife has probably either felt or is currently feeling.
    If you had to persuade her to quit it probably meant she didn’t actually want to. It’s time to move on and if you want to be married again perhaps while single you can think about what you want out of a relationship and work on communication skills.

    1. Affairs may be complicated when both parties have normal lives. (No firsthand experience, ok?) But I doubt that “affairs” with “escorts” will be complicated–beyond the logistics of the escort juggling multiple clients on their roster.

      1. Well yeah but what has he been telling his wife for two years? That’s what I’m amazed by. Excuses might work for a bit but eventually work trips, time with friends, etc start to seem a bit over the top. Unless I guess the wife has given up, knows and doesn’t care, is doing the same, etc.

      2. Skyblossom says:

        School might be a cover that works if he tells the wife he has to meet up with people for group projects or meet people to study. It could sound very reasonable and they would be people she wouldn’t expect to meet.

      3. Yeah, you have to wonder if he’s been in school the whole time though. I guess personally I’ve found that eventually things start to not add up if the person is covering for themselves. I’m just surprised he was able to keep that up for 2 years.

  7. Anyone else have the song “I’m in Love with a Stripper” in their heads now?

  8. Well deserved Karma? And you keep letting it get worse which is awesome. No way this girl stays faithful to you. She will definitely keep taking your money in exchange for the fantasy she provides you as long as you let her though.

  9. Skyblossom says:

    I find it ironic and hypocritical that you expect your escort to be faithful to you while you constantly, continuously cheat on your wife. Look at it this way, your escort makes more money if she forms a “perfect” relationship with you. She makes more money if she always agrees with you and has the same interests as you and always listens to you. She makes even more money if she can do the same thing with other guys at the same time. She has a lifestyle that she likes, it suits her for now and meets her needs.

    Another thing to realize. What is the one thing she knows about you beyond a doubt. She knows that you cheat on your wife. She knows that you lie to your wife. She knows that you don’t mind harming your marriage and she knows that you don’t work on your marriage. Why would she want that for herself? Why would she want you for a husband, the guy who lies to and cheats on his wife? She has multiple relationships with men who do the same to their wives, why would she want to get married at all when her view of marriage is so ugly.

  10. The LW is deep into a world of dysfunction and chaos. I’m guessing that there is also dysfunction in your current marriage (did you “rescue” her too?) and with any kids you have. Choosing a hooker fits right in!

    If you ever really want a “boring”, normal life free of all that, give up all of these dysfunctional relationships and get therapy to fix what is wrong that makes you seek out this kind of life. You can do it but it won’t be easy. Until then, you’ll keep choosing crappy relationships and making bad choices.

  11. Bittergaymark says:

    Wait, so she DOESN’T have a heart of gold? I simply don’t believe it… I also have trouble accepting that a prostitute would EVER sleep around…

    1. Skyblossom says:

      But deep in her heart she loves gold. Isn’t it the same?

      1. Skyblossom says:

        I am not knocking her for liking money. I think it’s funny that he doesn’t seem to understand that this is a business relationship, that she is a professional making a living and he is her client. It sounds like she is good at her profession, she did such a good job cultivating this client that he wants her to marry him. She may even have a real boyfriend who knows what she does for a living and is supportive of her life goals and who isn’t trying to change her. I think she’s good, very good, at what she does. She probably earns every penny.

      2. Seriously, she is an excellent businesswoman! Kudos to her. This guy is an idiot if he thinks he can get her to give up this lucrative line of work, even if he’s able to support her.

  12. This is frickin’ stupefying. First, you are cheating on your wife with a paid escort. So you couldn’t even go find a real girlfriend to cheat with. Second, you are 28 years married but still going to school in hopes of supporting yourself, so you are a middle aged guy with no decent means of supporting yourself and the reason you have not filed for divorce is that your wife is supporting you, and you need to use her until you are ready to get a job. Third, you believed an escort when she said she stopped for your love, You are so special to her that she begged you not to leave her, even though she balls men for money for a living, and you are nothing more than a regular. There’s a sucker born every minute. Fourth, you are shocked and hurt by evidence of her cheating/working, even though you are a cheater, but don’t even have the excuse of making your living that way. Although you kind of do, because you are getting support from your wife, and you are definitely screwing her in several important ways, if not having actually sex with her. Lastly, and most hilariously, you are writing to a predominantly female, feminist website for advice on how to make that work? So here’s what you do: You’ve been married 28 years and your wife isn’t making you happy. That’s obviously her fault, right? Otherwise, you would not have been forced to pay kindly sex workers to give you the help you need. I think you can use your wife’s obvious failure to live up to the terms of the marriage contract when you sue her for divorce. You can probably take for for everything, move your sweet baby into the house, and I’m not sure of the law here, but i think you can also force your wife to watch while you bang your escort/fiance. Be sure to tell the judge how your wife stopped meeting your oral sex needs, and that you didn’t get enough love as a child. Write us back and tell us how it all goes down. That’s gonna be good TV.

  13. I love how people like this always justify it by “The love is dead” or “my partner doesn’t understand me”. I have found in almost all cases, YOU checked out and stopped trying to be a good partner years ago too. I knew someone who was a chronic cheater on his wife, and she was desperately trying to make things work, and he would say “well the love is dead” when she was trying to re-establish intimacy, fun things to do together, communication, etc. He just wanted someone to stroke his ego, have sex with him, and not be required to do the normal not-so-fun relationship stuff (like meet each other’s needs when you don’t want to – not talking sexually).

    I’m willing to bet while he has this fantasy land relationship, his wife is trying to make things better at home, and he’s out with someone who is exposing him to everything every other John has, and taking his money, but because she doesn’t make him take out the garbage, or help with the kids, or deal with REAL LIFE, she’s the ‘one’.

    Summary – grow up, man up. End the affair, get an std test, be honest with your wife, beg her forgiveness and be ready to pack up your crap because if she has any brains, she’ll kick you out, take half your stuff, and find a man who values her.

    1. Skyblossom says:

      The proof of the lie that their marriage is dead is that his wife is paying for his education. If she thought the marriage was dead and that he would leave her as soon as he finished his education I doubt she would be willing to fund his education. The woman who loves him is the one who is supporting him financially and probably emotionally and probably doing more around the house since he went to school so that he has time to study. That’s the woman who loves him. The woman who doesn’t love him is the one he has to pay for every date. The woman he pays for every date knows that he is deluding himself, that he is a loser who cheats on his wife, a liar who can’t support himself.

  14. I want to know how you got her enrolled in school. Did you enroll her and pay for her classes? Or (more likely) she says she’s enrolled and is letting you give her money for the “classes”? No wonder she’s begging you not to leave…

    1. Skyblossom says:

      I was thinking the same thing. I had two roommates who would enroll in classes, get the money for them from their families, and then drop the classes and take the money.

  15. findingtheearth says:

    I think it is quite horrible you are still married to your wife. She deserves better than that. You need to tell her what you are doing and discuss divorce. I really hope you live in a fault state and she can get alimony or something from you.

    In regards to your escort, you really really really need to understand that she has power over you and is manipulating you. You do not love her. You do not even trust her, or else you would not be looking through her phone. You need to get over yourself.

  16. Avatar photo Astronomer says:

    Dude, let’s get real here. Medical assistants don’t make a ton of money. I’m sure this lady is super-excited to trade her potentially hundreds of dollars an hour job for a fourteen dollar an hour job just because you told her to.

    Here’s the Bureau of Labor Statistics Info: http://www.bls.gov/ooh/healthcare/medical-assistants.htm

    1. But– it’s love! Expensive, expensive love.

      1. Avatar photo Astronomer says:

        Ha! From personal experience, that’s the worst kind.

  17. There is so much wrong here that the fact that he was going through her phone (usually prompts a lot of comment) didn’t make it into top ten things wrong in the relationship. He should also read some of the letters (and responses) that just deal with that issue!

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