“The Girl I’m Dating is On Vacation with Her Sugar Daddy”

I met a girl about eight weeks ago and we really hit it off. On the second date she told me that she had previously planned a trip to climb Mt. Kilimanjaro in Tanzania with another guy. Climbing that mountain was her life’s dream. She was training five hours a day. She had only met the guy once before for a couple days and wouldn’t see him again until the trip. She explained that he was a “sugar daddy” whom she had met on an app. It was her first.

The trip of almost three weeks required her to be having sex with him and essentially acting as his girlfriend. She wants monogamy and I do also. She said she’d understand if I slept with someone else over the same time period but didn’t want us to automatically be “open.”

I flip-flopped emotionally trying to get my head and heart in the right place. She helped but had a harder time understanding why it was so difficult for me. I value the intimacy of sex with one person as a very important part of a relationship. When someone “devalues” sex by sleeping with someone else, it really pains me.

She left on the trip a week ago. She’s texted saying she has just had to numb out and put up “castle thick” walls. She says all the right words and totally avoids any comments or descriptions about him or their sex life, but I’m so distraught. I don’t know if I’ll be ok when she gets back. I might not even be able to approach intimacy.

Thoughts? — Not Her Sugar Daddy

My thoughts are that she is telling you one thing – that she wants monogamy and doesn’t want an “open” relationship – and is behaving counter to those words. My thoughts are that you likely have values that differ so much that it would be hard to overcome such differences and forge a strong relationship. My thoughts are that, after only eight weeks, you’re lucky you learned about your mismatched values early enough that moving on from this woman will be much, much easier than had you been dating a year or two. When she comes back from her vacation, let her know that, after giving it some thought, you’ve realized you are not a match, wish her well, and move on.

I have been dating an older gentleman for a couple years. He’s 60, and I’m in my early 50s with a teenage son. I’m divorced, living my own life and happy in my home; he’s widowed and thinking about retiring in a couple years’ time, where I have about 18 years left before I can afford to retire.

He has been asking us to move in with him, but there are several issues around this. His late wife passed over ten years ago, and her clothes are still in the closet, her books on the shelf, and her pictures of her parents (they died 20 years ago) and her furniture all over the place too. There are also pictures either of her, or deeply connected to her, in every room in the house, and her jewelry is still in a box on the dresser. My boyfriend is basically saying that he would love for us to move in but, unfortunately, there isn’t room for pretty much any of our own possessions (my son’s bed, my heirloom furniture, books, clothes, etc.).

He wants us to retire at the same time so we can enjoy “our twilight years” together. Obviously, I would have to contribute my and my son’s share of living expenses (my son is still at school) and to our retirement. The house was bought jointly with his late wife and was left entirely to him; he is leaving it to his stepson in its entirety (along with what is left of his pension fund) and has been very open about this not changing.

How do I tell him that there is no way I am doing this without coming across as the bad guy? He genuinely seems to think that this is the best deal ever for me. It isn’t even as though I will get an improved lifestyle out of this as I would face a seriously impoverished retirement and I can’t rely on his changing his mind. I feel as though he wants an unpaid companion to supplement the retirement he wants for himself and damn anyone else’s dreams!

I really just need to know I am not being the asshole here. — Trying not to be an Asshole

Why are you so concerned with being an asshole or coming across as a bad guy when your man friend isn’t showing the same level of concern about/towards you? I mean, I know the answer – you’re a Get X woman like I am and we are/were socially conditioned to put our own needs last and worry about everyone else first. But you know what? Fuck that. Where’s that going to get you in this scenario? In a house full of a dead woman’s belongings, with no room for your own stuff, with a man who not only isn’t promising you a rose garden, but is basically promising you no garden at all. You’ll be contributing to his lifestyle, not building any equity of your own, and seriously compromising your financial future. And for what? So you can live out your years contributing to someone else’s dream instead of your own?

Speaking of dreams, what are yours? I would spend some time thinking on that, writing them down, and maybe even brainstorming steps, goals, and hopes that support making your dreams come true. I might also make a list of potential roadblocks – things you have some or no control over – like job loss, health issues, and relationships that suck the oxygen out of your life and give little in return. Seeing potential plans laid out in black and white can go a long way in creating a path toward personal fulfillment. It’s like having a map, with potential detours for roadblocks. I’m willing to bet that NONE of what your partner is suggesting supports your dreams and that, if you’re honest with yourself, he is probably a distraction from the path that leads you to them. At the very least, the plan he’s offering to you would be a distraction.

If you enjoy his company and can continue to do so without compromising your own dreams, your own financial future, and your independence (which seems to be a point of pride, if I’m reading between the lines correctly), go ahead and keep seeing him. But if embracing his retirement plan as your own, years before you’re ready for such a step, and in a house that will never be yours and cannot even accommodate you, is part of the deal, I’d move on.

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


  1. Re Sugar Daddy. This woman is essentially a prostitute. Like Wendy says, she is also talking monogamy on one hand and selling sex and companionship on the other.
    Sounds like she is saying she will be faithful to you as a romantic partner but might also continue have sex as a business deal.
    No way this will work. Plus why does she not have enough drive or talent/education to finance her own dreams? If this is how she is fulfilling a “life time dream” she sounds lazy and unfocused. She certainly does not seem to regard sex as “special”, as you do.
    If she was that excited about the idea of a relationship with you, she could have backed out of the trip or found another way to do it. What if you do keep dating or start a serious relationship, and she decides she needs a new car or some diamonds “right now”? Move on!

  2. Wendy’s advice is great here. While these might be the right relationships for somebody, these aren’t the right relationships for either of you, LWs. Cut your losses and move on.

  3. I don’t think that you need to wait until she’s back from vacation screwing a stranger to break up. Leave her a text that she’ll get when she comes back and move on now.

  4. I have mixed feelings on LW#1. I wouldn’t call this woman a prostitute. Nor is she cheating on him. She is honoring an arrangement she made prior to meeting him. She’s exchanging sex for a travel adventure. First and probably only time she will engage in such a bargain. If LW and she met ten weeks later than they did, they’d each be starting with a clean slate. Sexual history is history, not a forecast of future. She was upfront and told him about this on second date. It is kind of an empty gesture to say she doesn’t expect him to be monogamous in her absence, because she had her 3 weeks line up and he obviously did not and isn’t into casual sex, so if she knows him at all, she knows he won’t be having sex while she’s on her trip. Reasonable chance they could both be monogamous after her return. Also, good chance he won’t be able to get past this. He needs to know himself and that will properly guide his decision. I see no advantage in sending a breakup note/e-mail now, rather than talking with her upon her return.

    They do have divergent values, how different is hard to say. He doesn’t know her well enough to say. So, I think it comes down to how interested in her he is, whether he thinks he can get over this, what they have in common in values and life plans/outlook/interests.

  5. Nice optimism from Ron. I don’t mean that sarcastically. And ok, call it transactional sex then. Go ahead and talk, but I just don’t see it working out.

    1. Maybe, maybe not. I’ve had transactional sex before. Now happily monogamous. It can happen but there needs to be some serious discussion in this situation about what that means.

  6. LW1: It’s only 8 weeks: move on already, just end it or ghost her, she won’t scratch her head wondering why. You value “the intimacy with one person only as a very important part of a relationship”. But you date a prostitute, don’t you see the contradiction? It is doomed from the start, it will never work. Unless you appreciate this kind of mental torture, to imagine her with her old client. Plus she is playing you. It is not so much about the Kilimandjaro, this is her way to make it acceptable to you as a sport exploit. She goes on Sugar Daddies sites, she is venal, she sells her body as a way of living, she doesn’t see so much the problem for a monogamous BF… This client is not her first, surely, and probably not her last. Come on, there is a huge value problem here. She is no girlfriend material, and even less no wife material, she wants her cake and eat it. Just move on and find a woman you can be proud of and admire, who can be reliable, this is such an important part of love from the start.

    LW2: I really don’t get why you would impoverish yourself and lose your golden years with someone who wants you to retire prematurely against your best financial and personal interest. Wish him well and let him go. You can find a partner who is more in tune with your stage in life or who at least will respect it. Please don’t make such an enormous mistake to become his care taker, be more confident: you can do better. You can be fine also by yourself for a while: much better than the self-defeating deal you are facing here.

  7. Anonymousse says:

    I am remarkably surprised that you continued to see her after she told you about this arrangement if you view sex as special or sacred. You two just do not align in values. If you want a fling, or you’re young and need to learn lessons the hard way, sure have fun, but she’ll break your heart. I’d save yourself the heartache and move on now.

  8. LW2: no no no…do not give up your financial security for this guy! If he can’t respect you wanting to protect your and your son’s financial well-being, he doesn’t truly care about you.

  9. Yes Daisy, LW#2 is dating an unbelievably selfish user. He expects her to give up her job and financial future, yet he is going to leave everything he owns to his stepson. If she accepts this offer, she guarantees that she will end her life in penury. He wants them to enjoy their twilight years together? Nope, he wants a caretaker and housekeeper for his twilight years and will be dead for her twilight years. It’s clear all his affection remains with his first wife.

  10. I don’t think that it is clear that the couple in LW1 don’t align. People can engage in sex work and still value intimacy! If he is going to shame her for having done this, I would want them to break up for her sake, but I don’t see any reason to think she is not capable of a monogamous relationship now that she is dating the LW.

  11. And I wouldn’t call her a sex worker. She doesn’t support herself through sex. She is trading sex for a vacation which she couldn’t otherwise afford. Is that a once and done before she met LW? Is it a multiple times and now done? Is it a part of her lifestyle, which she will continue? What she is saying to LW is that it will not continue.

    She has an ethics issue: she made a deal with a Sugar Daddy, whom she sought out. He clearly had already paid for the expensive vacation. She felt the honorable thing was to complete the deal. She didn’t have a bf at the time. Yes, she could have backed out. She also could have told LW she was on a 3 week vacation with grandma. She told him the truth.

  12. And I wouldn’t call her a sex worker. She doesn’t support herself through sex. She is trading sex for a vacation which she couldn’t otherwise afford. Is that a once and done before she met LW? Is it a multiple times and now done? Is it a part of her lifestyle, which she will continue? What she is saying to LW is that it will not continue.

    She has an ethics issue: she made a deal with a Sugar Daddy, whom she sought out. He clearly had already paid for the expensive vacation. She felt the honorable thing was to complete the deal. She didn’t have a bf at the time. Yes, she could have backed out. She also could have told LW she was on a 3 week vacation with grandma. She told him the truth.

  13. Regarding her client, it is not so much an « ethical issue » as a « commercial issue ». She made a deal and to break it /not deliver would be expensive for her, she probably would have to repay her part of the trip’s costs and she can’t afford it. Plus she wanted obviously to do it. She is an occasional sex worker. It pays her some luxury vacation. She says it is her first. Perhaps but she does it so she is. There is nothing wrong with it, but this is a difficult issue to deal with at a start of a relationship, especially if there are talks of monogamy and she does it anyway. Even if she is honest, what strikes me is that she is trying to inflict him her way of life in a detailed manner and he should go with it, she confides in him and doesn’t see why it is so hard for him. She is ambiguous and what she is doing right now is to have it both, the monogamous boyfriend and the occasional lucrative sex business. Regarding ethics and honesty, I think it would have been more OK for her not to commit to a monogamous relationship, to do her trip without explanation (she doesn’t own any account of her sex life as long as there is no exclusive relationship), and then to make clear choices about the LW. What she requests of him is not OK, it is rather torturous. At the very least, he should wish her a good climb of the Kilimandjaro, stop the communication and tell her to maybe recontact him if or when she is ready to start a monogamous, exclusive relationship, and then he might give it a second thought. It is then for him to see if he can accept her previous choices (his problem, he seems to struggle), if she is reliable in her commitment (her problem). But I would rather walk at this point. Too much trouble and heartache.

  14. It’s ok to not be comfortable with dating someone who engages or has engaged in sex work. It’s good she was honest but you need to be honest if this is something you can get over (being the one time – if she does it more than that is different) or if you’re not ok with it and if not,then move on. You don’t owe it to them to stay just because they told you but you do it to be honest in return. To me I think it’s normal not to be ok with being someone who makes money by trading being a girlfriend and having sex with someone. To me if shewas truly serious about you as well she wouldn’t bother with this trip but she’s still going so I think that tells you she’s not overly invested and neither should you.

  15. I think society has a long way to go if we’re going to criticize the choices this woman made. She wasn’t dating at the time she made the arrangement. She wasn’t hurting anyone, was honest about it from the beginning and handled it as sensitively as possible.

    They clearly aren’t a good match, as he’s wondering if he’ll ever get over it. He sees sex as devalued. That’s fine for him, but it doesn’t make her decisions any less okay. I had an ex accuse me of being “kinky” because I’d left my socks on (he was in a hurry!). He said he couldn’t be with someone who just didn’t respect The Act. Yeah, different values. They just aren’t compatible. Move on already.

    1. If someone sells their body for money, that is their choice. But it is also our choice if we wish to criticize it. Would you be okay with this if the LW was your son?
      Be honest now…would anyone here be okay with their son dating…and potentially marrying a prostitute who may or not may be giving up her former occupation?

      1. Honestly, yes. I don’t care who my son dates or marries, as long as he’s happy.

        It’s clear from your comments on this and other posts that you’ve got a problem with women. Sorry about your misogyny. Maybe some therapy could help with that.

  16. Listen to the first post by @fyodor
    How can she really respect you after that. Another guy is digging in the guts of the girl you like while you agonize for weeks? The only reason you would stay is if you absolutely have to. And most women dont respect that type of weakness.
    And you wont respect her either. If you were okay with this, you wouldnt be here talking to us.
    Havent you been stood up by a woman before? Most men say they have. Women dont have a stellar track record with keeping their dates. She could flake out on the guy if she wants to. Theres no real obligation there.
    She could have camcelled, and if she wants to go so bad, you could have taken her. Or yall could Have made it a plan and goal. Why build a memory with rando sugar daddy?
    Respect yourself. Use this three weeks to work out or better yourself in some way and be more ready for the next woman. Raise your standards for yourself and the woman you choose. Plenty good women. Give one a chance.

  17. No misogyny here…happily married going on 10 years. Perhaps you could make better use of the suggested therapy as you don’t seem to believe your family members can do better than some call girl

    1. Again, it’s absolutely fine not to want to date a sex worker yourself, but this dude is absolutely engaging in whorephobia here – a type of misogyny which acts to control and police women’s behaviour – with derogatory phrases like “some call girl” and “aim higher.” The paternalism is gross too.

      1. Whoops, this was supposed to be a response to @Ron’s comment below.

  18. Seriously though most parents would think/expect their children to aim somewhat higher for a life partner. Even the LW isn’t fine with it

    1. Oh, you’re married? My mistake! Obviously you can’t be a misogynist! Just like how you can’t be racist if you’ve got black friends, duh. /s

      Nobody is telling this LW that he needs to be ok with this. On the contrary, he’s being advised to end the relationship. There’s nothing wrong with not wanting to date someone who is actively sleeping with someone else.

      There IS something wrong with what you’re doing – denigrating sex workers in general because of their profession – and yup, it’s called misogyny.

      1. Sex workers include men as well as women. I don’t think misogyny is a requirement for not wanting oneself or relative to have a relationship with a sex work. A lot is prudishness and the American attitude toward sex. As I wrote upthread, I don’t see this woman as a sex worker.

        I hoped the OP had updated after his gf returned from her trip.

      2. ”There’s nothing wrong with not wanting to date someone who is actively sleeping with someone else”

        So in other words you are saying there is nothing wrong with not wanting to date sex workers.

        And yet I’M the one denigrating sex workers?

      3. Yes, @Reilly. Everyone who wants a monogamous relationship is denigrating sex workers.


  19. I feel for the girl that so many of you are referring to as a “prostitute” and “sex worker”. Regardless of your particular moral standpoint, which is your opinion and how you want to live your life, not the Right Way for the whole world, this trip will no doubt be an incredible experience for her. One that she’ll be proud of and remember for her entire life and one that she’s been preparing and training for. On the other hand, this guy might be great right now, but who knows if he would ever have any importance in her life? Sure, they “hit it off”, but they only met 8 weeks ago. It’s easy to hit it off with someone when you’re dating, that doesn’t mean they have a marriage in their future. I also think we have to take her at her word in this instance. She was upfront, said it was her first time doing this. She doesn’t owe anything to this new guy. She could have easily told him that she was going off with her family or on a trip with friends. I imagine she’ll have a fun time and enjoy the sex and the company. After all, the guy must be interesting, in good shape and have enough money to show her a great time. That’s why I don’t think this new guy should have allowed himself to become emotionally attached after finding this out, but he did. It’s probably best to walk away and realize that this is a bad situation for him, but I wouldn’t put so much judgement on the girl.

Leave a Reply

Your email address will not be published. Required fields are marked *