“My 41-Year-Old Boyfriend Still Lives With His Parents”

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I’m 23 and my boyfriend is 41. I’m finishing up my college degree, so I’m still living at home with my parents for a few more months. My boyfriend lives with his parents – he claims it saves money and is easier. He also said he was single before me, so he didn’t feel the need to have his own place. Since we’ve been dating, he was crashing at one of his rental properties, and he recently remodeled and sold it. For weeks I was under the impression that we would have that house as our space, and though not ideal, I was going to take what I could get. Now that he’s just sold it, we have no space to be together or have any alone time. My parents are not accepting of me being in a relationship, and being intimate at the house of his parents (whom I still haven’t met) is weird and limiting to me.

We’ve been having so many disagreements lately, and I feel that not having our own space is making it worse. We would have been able to spend all weekends together, but now that’s out of the picture unless he gets us a hotel room. I don’t want to feel like his mistress, and I shouldn’t have to. I don’t know what to do or where to even begin with him. He takes everything as a personal attack, so my attempting to talk about it with him would implode. Help!! — Not His Mistress

I know you don’t want to feel like his mistress, but I think you… might actually be his mistress. There are so many red flags in this picture – like the huge age gap (41-year-old men who date 23-year-old college students are usually creeps, let’s be honest) — but the one that is most telling is that your boyfriend lives with people whom you haven’t met. If you’re his girlfriend whom he cares about, why hasn’t he introduced you to his parents? There are two main reasons: 1) he’s ashamed of your relationship or what his parents would think of your relationship; 2) it’s not his parents he lives with, but a wife and possibly kids. My money is on the second.

Look, just get out of this relationship. No good will come of it. The guy is shady. At the very best, he’s a 41-year-old who doesn’t have his emotional shit together enough to live independently. At worst, he’s cheating on his wife with you and lying to you about it. You aren’t even getting along anymore. You’re frustrated, he takes everything as a personal attack, and you have nowhere to even be alone together. This relationship sounds miserable. Move on already. I promise that there’s a better match for you than some loser 40-something creep who’s lying to you.

I’m in my early 20s and my boyfriend is in his early 30s. We live separately. He sent me a video of him in his new apartment and there I found his ex-wife’s picture displayed prominently on his living room wall. Since then, I have decided not to talk about it although I feel he still has something to do with her and he’s not telling me. Am I overreacting? — Confused

No, it sounds like you’re under-reacting, actually, because your reaction is… to do and say nothing. Ask your boyfriend what’s up with the pic of his ex-wife. Are they still very close friends? Do they share children together? Is it an old family photo? Is he trying to make his kids feel comfortable and like their father’s home still includes a place of respect for their mother? I mean, I don’t know. There are so many reasons a man could have a picture of an ex on his wall, but unless you ask him why he’s chosen to display such a photo, you won’t have any idea and will feel suspicious and weird about it. You don’t need to over-react, but react, you know? It’s ok to question behavior that you don’t understand in someone you care about.

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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. Another Jen says:

    The best possible reading of this letter is that you’re dating an emotionally stunted 41-year-old who lives with his parents and can’t have a mature discussion about his living arrangements with his college-age girlfriend without melting down. If everything is completely on the up-and-up, he’s an immature cheapskate who’d rather save a couple bucks than have a normal, independent adulthood. And, like Wendy says, I highly doubt everything is on the up-and-up.

    There’s so much wrong here. You are wasting your time with a deadbeat loser. Run far, and run fast. There is so much better out there for you…at 23 (or any age, the last thing you should be doing is “taking what you can get.”


  2. Avatar photo Prognosti-gator says:

    “My parents are not accepting of me being in a relationship”

    I don’t know your parents, but I’m guessing that isn’t the case.

    I’m going to go out on a limb and guess that it’s more likely “My parents are not accepting of me being in THIS relationship.” In which case, they can join the club.

    1. Not His Mistress says:

      My parents are of different faith and do not believe in dating before marriage. I am not even allowed to wear jeans sometimes, nor stay out past certain times at night. I am of a different faith and am just trying to hang in there until I finish my degree and can live my life the way I want to.

      1. Your parents sound really restrictive and it must be tough but I promise the answer isn’t to date the first crappy guy that shuffles along. Once you’re out on your own take the time to unpack what sounds like a pretty hard upbringing and you’ll see you deserve much better.

      2. Karebear1813 says:

        I would suggested dropping this guy and finding a place for you to live on your own once you leave your parents home.

        It would be extremely bad for you to move from your parents home and into a place with a 41yr old man who you have concerns about. He is the definition of RED FLAGS!

        And I think due to your faith/maturity level- you are easily able to manipulate and be gullible.

        With that being said, partners do not have to introduce you to their family until they feel comfortable – usually when things get serious is when someone introduces you to their parents. I would think a year of dating would be considered long enough to know if you are serious about someone. Just because you are dating and or title yourself as bf/gf does not mean you have to be introduced right away.

      3. Not date before marriage? Or do you mean no intimacy before marriage?

  3. LW1 – Generally speaking, men who are 41 and still living at home with no desire to move out date women significantly younger because women within their appropriate age range won’t date them. This guy sounds like a loser. Time to move on.

    LW2 – Yes, you need to ask. I had an old coworker who had a framed photo of her and her ex-husband from when they were teenagers in her home and it was not because they were still involved or in love with one another. To her, it represented good times from her youth or something. But on the flip side, something similar once happened to me and they were not still involved, BUT my then-boyfriend was a deeply sorrowful man and still processing his divorce/not emotionally available… the photo showed up right around the time that he started cheating on me with the woman who is now his second wife. SO. Ask! It’s the only way to get clarity.

  4. “he claims it saves money and is easier.”
    LOLOLOLOLOL forever! Yes, it generally IS easier to mooch off of other people and never grow up.

  5. LW1: This guy gets agitated every time you bring up his living situation because he has absolutely zero intention of changing it, and he is annoyed that you’re questioning him and not falling for his BS anymore. Take everyone’s advice and dump him already.

    LW2: What do you hope to get out of current strategy of not talking about the picture and stewing about it privately? Your BF isn’t a mind reader. But more to the point, why is it that you’re afraid to ask him about the picture? Do you suspect the answer is that he’s still hung up on his ex? If that’s the case (and you don’t know that it is), then you might as well get it out in the open. Not speaking about something doesn’t change the facts.

  6. LW2 if he has children, then I can see a reason for the picture being there (though hopefully it is one the kids are also in.) If not, then that’d give me pause for thought. Had an ex who did this, and he did it to make me insecure. It worked. And it’s working on you. Maybe he does have a reason, so just ask him, and base your reaction on what that reason is. If it is bothering you (it is) no point in pretending it isn’t.

  7. anonymousse says:

    I know it’s hard to read everyone saying exactly the same thing but you know this guy is a total loser, right?

    At your age you shouldn’t be dating a 41 year old loser. Trust me on this. Move on. I know you can do much better than this guy. He knows it to, which is why he gets angry when you ask questions because he doesn’t have any good answers and he knows it. He sucks. You deserve more and better and even he knows it.

    1. anonymousse says:

      Ugh, sorry I can’t edit. I know the difference between too, to and two.

  8. Bittergaymark says:

    LW — The main issue here is the age difference. Aim higher, LW. So many young women things that dating old men makes them mature. No! It makes you date a fucking idiot. MOA.

    LW2 — OMIGOD! A picture of his ex on his wall. It’s over! (Yes. — That’s sarcasm.) Why STRAIGHT people are always so fucking dumb about this petty bull shit baffles me. Then again… the stupidity DOES explain all the WHOOPSIE babies. I get it. Birth Control is hard. Don’t try to walk and chew gum at the same time, folks!

  9. ele4phant says:

    I don’t understand people in their early twenties who date people so much older. I mean, there may be rare instances where two people really do click and the age difference is not a big deal, but on the whole, when I was in my early twenties someone in their forties might as well have been an AARP card caring senior citizen.

    I had no attraction at all to older men. Even now, I’m pretty much only attracted to men around my age and phase of life.

    Who finds someone so much older attractive? Just, cannot wrap my head around it. Is it Daddy issues or something?

    1. Bittergaymark says:

      I don’t get it either. And now that I am older — I really don’t get it. Only losers are single post 35.

      1. Whoa, what?! Lots and lots of people are over 35 and single, for various reasons. Doesn’t make them losers at all.

    2. I have had a few friends over the years who liked dating significantly older men and they all had some issues. One had a very absent father and for a little while in our 20s dated a guy who was in his 40s who did a lot of drugs and she called him Daddy.

  10. Holy cow, this somewhat sounds like what happened to me in my early 20s. I was dating an older guy (I know, I know) who never took me to his house because he said he had family staying there. He sure did… His wife and kid! The red flags were slapping me right in the face but I was too blind to see them. I was young and inexperienced and wanted it to work out so I didn’t let myself think outside of what I wanted the truth to be. This is a bad relationship LW1 is in, even without the shady aspect, but I’d bet money this guy lives with his wife and kids, not his parents.

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