“My Boyfriend’s Roommate Owes Him Over 10k in Back Rent and He Still Won’t Kick Him Out!”

I’ve been dating the same man for 3-1/2 years. He has a problem with letting people take advantage of him. He found a roommate on Craigslist two years ago to bring in some extra income since he’s retired. This roommate supposedly produced some film projects in the 80s, is now a has-been, and “has working on some new projects.” He also claims that his father is a millionaire; yet, he is always late with rent, doesn’t pay in full (if at all) and makes excuses like his “new contract” has been postponed (several times).

I knew this was a serious problem over a year ago, when he owed my boyfriend 2K, and I begged him to get rid of him. I was upset because I was paying for most of the things we did when this loser first moved in since my boyfriend had other debts he was trying to clear, and he would then go without necessities like food because this renter didn’t give him what he owed him. My boyfriend has kept him there because this con-artist has made promises to put him in these projects and make him famous! Not one of the contracts or projects since he has moved in has materialized, and now, two years of excuses later, he owes my boyfriend roughly $10,000. I said it’s time to throw him out, especially since there’s no lease and no proof of what is owed, if he tried to sue him.

Now the roommate’s dad just died. Even though he owes my boyfriend $10K and is “a millionaire’s son,” he asked my boyfriend for $2K cash (at Christmas time) so he could pay “his shared portion of funeral” to his brothers, when the mother is still alive. MY BOYFRIEND ACTUALLY GAVE IT TO HIM; he is not family or a friend! Cash was not needed — a funeral home will take a life insurance policy to pay for everything and refund the difference.

My boyfriend has no problem telling me off and defending this idiot’s behavior when the topic comes up. However, he has no balls to tell this wimpy man that time’s UP! Even when my boyfriend told him months ago that I may be moving in and he may need to move out, he replied, “I might not be ready to move out yet” and my boyfriend didn’t say anything moreto him. I told my boyfriend he needs to stop being this other man’s bitch, letting him dictate what goes on in his own house, and deciding when, how much, and even whether he’ll pay his share of the rent at all.

I hate to stand by and watch someone financially take advantage of my boyfriend and string him along with promises of stardom and paying him back. I get sick listening to him brag about this person, telling others about what he has promised him. Am I wrong to tell him it’s time to grow a pair and get rid of this con-artist? Or should I just walk away and let him crash and burn alone if he won’t get rid of him, even though I love him and he says he loves me? It would kill me to keep quiet and watch this continue – it’s like watching someone die. — Exasperated

It’s time to walk away and to say a little prayer of thanks for the con-artist that he was able to expose so many of your boyfriend’s flaws before you actually moved in with him or committed yourself more than you already have. Your boyfriend is the wimp. He’s cheap, he’s naive, he’s foolish, and he doesn’t seem to respect you very much. I’d also be wondering if the empty promise of stardom was truly the only reason your boyfriend continues to let a man live with him for free for two years. If it is, the crash and burn you mention is going to be epic, and you should distance yourself as quickly as you can…


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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. Yep, you need to walk. BF is being a dick to you and pretty much an idiot. Also, even without a lease this could take a LONG time to kick him out. Freeloaders like this will learn or know the laws and he could spend tons of money getting him evicted if he doesn’t go willingly.

    1. Exasperated-original poster says:

      At this point, without a lease and proof that he hasn’t been paying him, I don’t even think he has a leg to stand on to get what’s owed to him, ever. It will be his word against the tenants and that’s why I think it’s time to cut the losses before they get any bigger.

      1. I totally agree.

  2. “I was paying for most of the things we did”: if someone is taken advantage of here, it is you. All what you say about your boyfriend, you could apply it to yourself. You are being used, mistreated, disrespected.
    Your BF can do what he wants with his money. He can host a friend (?) for free.
    You can only decide what you want to make with your time, your affections, your expectations, your money. Kick him to the curb.

    1. LisforLeslie says:

      Yup -you’re paying more than 50% of your activities because your bf can’t pay because he’s paying down other debts and is paying for his loser roommate.

      Get out. Get out now. If you stay, then you have to give up and understand this will always be how it is.

  3. He is holding out to get paid. He doesn’t want to believe his roommate is who you say he is because it makes him a poor judge of character. Kicking people out isn’t easy. The roommate has legal rights and if he doesn’t leave quietly, your boyfriend will have to evict him which is an ugly process. Also there is probably an activity that the two of them are sharing in that makes extrication difficult.

  4. Bittergaymark says:

    Neither of you is exactly great with numbers… your boyfriend is currently owed $12,000. Not $10,000. At any rate — the larger question remains… who’s the bigger fool here? The fool or the fool who dates him? I say the latter.

  5. This part really stuck out to me: “My boyfriend has no problem telling me off and defends this idiot’s behavior when the topic comes up. However, he has no balls to tell this wimpy man that time’s UP!”

    Your boyfriend has very clearly chosen this guy over you. For whatever reason, he cares more about his roommate than his girlfriend. Idk maybe the guy has compromising photos of him, or maybe he just doesn’t give a crap about you. Give thanks that you dodged the bullet of moving in with your boyfriend, because you surely would have been stuck with two loser roommates and not the just one you were dating, and then move on.

    1. I was having the same thought. Seriously, leave these two to be with each other in this continuous financial hot mess. Let your (hopefully now ex) boyfriend be so he can find out the hard way and crash n burn on his own. You do NOT want to be dragged down by either him or the freeloader roommate.

  6. Huh, this is almost exactly the plot of the classic Jack Black film “School of Rock”. Are you Sarah Silverman? Any chance the roommate is going to use your bf’s identity to get a substitute teaching job, then turn his life around through his dedication to making art with his new lovable-rascal students?

    You absolutely should dump this guy. Why are you even with him? You don’t respect each other, and you don’t even really know if he loves you! There’s nothing to save here. Be grateful that you weren’t financially entangled with him.

  7. Carolina Blue says:

    No relationship is worth all of this- financially or emotionally. MOA please!

  8. Avatar photo Guy Friday says:

    Respectfully, am I the only one here who got a vibe that this LW is almost equally pissed that SHE can’t be the one to take advantage of her boyfriend’s doormat tendencies?

    1. Bittergaymark says:

      There sure IS an awful lot of angst over the fact that she (gasp!) must pay for everything…

    2. LisforLeslie says:

      Same, that’s why I called out the 50% – if she’s pissed because they go to olive garden and she’s paying 2/3 the bill, or always footing the grocery bill and chipping in to the cable bill, then yeah, she’s right to be angry.

      However… if she’s ordering 2/3 of the bill or expecting him to pay because he’s the man… then nah, she’s just mad because someone got the gold digger role first and doesn’t have to give oral to get the money.

    3. dinoceros says:

      I totally agree. Her tone when she talks about telling her boyfriend what to do makes me imagine her standing there and screaming at him about what a doormat he is.

  9. Your BF’s roommate is probably entitled to some squatter’s rights by this point so he’ll likely never leave. This situation is too perfect with him. MOA, LW. Your BF will never stand up for you or side with you if something serious happens…

  10. You are the one dating a con artist.

  11. Its really not LW business what boyfriend does with his finances and he doesnt seem to be the one upset about it. I didnt read in the letter that he was confiding his frustration to her. His money his choice. Him telling her off is because its not her business. He doesnt owe her any explanation. If she feels she is being taken advantage of then she should leave the relationship.

    1. Well If she knows he’s telling her. And it is her business if they are discussing living together.

      1. Becasue shes intrusive and wont leave him alone about it. And even if they live together doesnt give her the right to intervene in his finances. His money isnt her money. They are not married. If she doesnt like the set up she doesnt have to move in.

      2. Allornone Saying if he can’t pay the rent that’s his business, well it will be your business when you share a lease or you’ll be evicted. Just saying someone else must do it doesn’t magically make it so b

    2. Allornone says:

      When they move in together, it will be her business to an extent. I have no idea how much money my boyfriend has and couldn’t care less what he spends it on PROVIDING he’s able to cover half the rent, the electricity, and our streaming services while I cover my half of the rent and all the groceries and household needs, just like we discussed before moving in. If he can’t, then that’s a problem because I might not always be able to cover it and bills still need to be paid. OP’s boyfriend needs to be able to contribute to the household expenses and she needs to be able to depend on that. If they make similar wages (I don’t know that they do), ideally, he should be paying about half. But if he’s giving away so much that he can’t cover his agreed upon share, that would definitely be her business as it could impact her on a number of levels from credit score to possible eviction.

      1. You for sure need to read Wendy’s advice on what you should’ve discussed before moving in.

      2. No its not to any extent unless you combine your finances together or are legally married. Which is taking a big risk if you are not legally married. It doesnt change if its a sister, bf, gf, or bff that you are living with and splitting bills with. It’s a risk you are taking when you choose to go in with a person. No different then going in own a loan with a person you don’t share income with. Its a risk. Yes you do discuss bills and etc but you cant dictate to a person what they do with their money regardless of relationship status. BF/GF are in legal terms roommates nothing more unless the state the person resides in can claim common law and they have to fall under the common law statue. If your bf/gf dont have money for food or rent and are carelessly not helping pay bills then you get out and if you see since before then duh you dont do it. Courts hate when people play house with no legal binding because they fight over the petiest shit such as furniture they went in together on then its a fight for who should get what or who owes who what. My husband never had any say about finances prior to our engagement and we discussed our finances during our engagement period.

      3. Poppy, when you move in together, you do need to know some basics about your partner’s finances, beyond just “can you cover the rent?” You want to know that there’s nothing big going on behind the scenes that could blow up, and that they could handle some emergency expenses. And if moving in is a step toward marriage, then you do need the full picture of their finances well before you’re legally married. You’re right that if you’re just living together it’s not necessarily your business what they spend their money on, but it’s really dumb to be legally bound to someone on a lease and heading toward engagement or a marriage license and have literally NO idea of their financial picture.

    3. anonymousse says:

      Of course he was confiding his frustration.
      Shockingly, some partners discuss what’s going on in their life, especially when their SO is paying for everything, they can’t afford food, and their freeloading tenant owes them thousands of dollars.

  12. Bittergaymark says:

    More like he tells her all about it as a way of explaining why he is always broke… the LW is right to be irked.

    1. However she knows she knows. He could just be bitching, she could be intrusive, but he is still choosing to tell her so it became her business.

  13. he really wants to be in these films, enough to not care about the money. You’re never going to be able to compete with this. I’d move on were I you, and find someone who isn’t so preoccupied elsewhere.

  14. Juliecatharine says:

    Am I the only one who thinks they’re lovers in the nighttime?

    1. Bittergaymark says:

      Why even bother with the LW though? I dunno. Seems very doubtful.

      1. Juliecatharine says:

        True, BGM. It’s his age is what made me wonder. A lot of folks from older generations don’t seem to have abandoned the closet.

      2. Bittergaymark says:

        True, true. True.

  15. Northern Star says:

    Your boyfriend is a gullible sucker. And the lure of being famous is more important to him than… eating. Just dump him. If you stick by him any longer, YOU are the gullible sucker.

  16. LW, I think you need to leave this guy. If you choose not to, I do have an idea.

    So I think your boyfriend really likes to feel needed and feel helpful. I am guessing that this con man can show a problem and let your boyfriend be the hero. While you are badgering him and belittling what he thinks are “good deeds”. Most enablers are the nicest people you will ever meet. So I would suggest that you start asking your boyfriend for help more and really be appreciative when he does. When you talk about the next steps in your relationship, focus on the positive. But if you call him “This man’s bitch” , it drives him away from you and towards the man that is kind to him.

  17. This man has something over your boyfriend blackmailing or has some sort of Wallis Simpson hold. Why YOUVE put up with this situation for so long is beyond me. Your boyfriend has made it clear where his loyalties lie….what more you think you could say to make him change his mind I dunno

  18. dinoceros says:

    I think that you’re being kind of hypocritical here. If you don’t like how your boyfriend is doing things and if you feel like it’s unfair to you, then dump him. You’re doing the exact same thing that he’s doing — sitting around watching things go badly and doing nothing about it. You don’t have to have a boyfriend who lets a con artist walk all over him any more than he has to let a con artist walk all over him. After this much time, you have all the evidence you need to know that your boyfriend doesn’t care that this is happening and he isn’t going to fix it. For you to continue to stay with him is just as ridiculous as him letting the guy keep living there.

  19. So, LW is all in and supportive of her bf, if only he could turn into an entirely different person. That’s not how it works. That’s not how it can possibly work. You take him as he is or you MOA. Sure, minor changes to annoying actions might be possible, but you’re seeking an entire personality transplant.

    I think the roomie is the full-time bf and you’re the side-piece.

  20. LW1 Wow!! Those kids are not just THAT WOMENS KIDS! Your boyfriend is raising his kids plus 3 other kids he helped raise when no one else was there. If he is tired of raising the 17yr old and 14 yr old then he knows where their momma lives and families lives. You do not sound like a understand and supportive person and this family dynamic doesnt sound like one fit for you. I am curious to know why the mothers youngest two children are calling him dad because I didnt see in your post that he was raising them as well. Are they his children and does he care for them?

    1. Exasperated-original poster says:

      First of all, thank you for all of the feedback…some I already knew anyway, but maybe needed to hear that I wasn’t crazy. Though, I guess I better learn what some of the abbreviations like LW, since it is referring to me. OK couple of quick answers/ additions…
      -He did originally tell me all of this as a means to explain why he didn’t have any money to do anything. But I think it’s gone on long enough and when he can’t meet his own expenses (nothing that inc me), that is wrong.
      – I pulled a report on this renter and he’s had 35 addresses within the last 20 yrs or so and sent this report to BF to prove this guy is bad news and can’t be trusted, but now he’s giving him more time since “his father just died… give him a break!”
      -Yes, he is trying to hold out to get his money, but I really don’t think it’s gonna happen since he made the promise to pay what he owed him a year ago and the more time that goes by, the more he owes him.
      -No, I’m NOT a gold digger, nor am I jealous someone is taking advantage instead of me. I do not run his bills up, even out to dinner. In fact, I will order “light” not to cause a big expense. I AM NOT HIGH MAINTENANCE by any shape or form. For those first 2 yrs I paid for most of our “dates”, but he has been trying to make it up to me now over the last year, but I still don’t make him pay all the time. However, with this recent argument, I told him if he wants to go out, I won’t pay for anything, while he is supporting this freeloader and no I don’t demand that we have to go anywhere. We can sit in for all I care.
      -Why do I feel it is my business? I am not a lover in the nighttime to him. This man has asked me several times to marry him and wants to spend the rest of his life with me and I won’t let him buy me a ring yet. He also wants us to live together (he wants to move in with me). If we are going to be a married couple these things will affect both of us. I want to be sure there are no existing problems if we chose to spend the rest of our lives together. I will not move towards long term plans, if things are going to be this messy.
      -Do I think he’s gay? No, but he is a ham, who is falling for this “I’ll make you a star” line.
      -Yes, I have said myself and him that “you are doing to me, what he’s doing to you…maybe I am the fool!” But he doesn’t see why this situation should bother me and thinks it has nothing to do with me. If he won’t stick up for himself, I am concerned that he won’t stick up for me, if we are to stay a couple and/or get married.
      – Yes, I have stated to him that he is choosing this renter (empty promises and hopes of stardom) over me.
      -Yes, he does want to seem helpful and needed, but I don’t believe this is a good cause and is a con of epic proportion. He will not give a homeless person on a corner $1 and will yell out “get a job” and have a fit if I gave them anything, but has no problem letting this guy get away with so much more.
      -He also craves attention and wants my support on everything he does. I do try to support him with decisions, but this one is baffling…I just don’t understand it and can’t. I tell him not to talk to me about him, if he doesn’t want to hear negative things, but he does anyway. I shouldn’t be asked to be kind to him either if he comes in the house. I figure saying nothing to the roommate is more than respectful in this case.
      **Bottom line** I love him, he says he loves me and wants a life with me. I am trying to show that I care about him and have asked him to tell me what his game plan is and I will either take it or leave it. I think it is a fair suggestion to set a deadline and let the roommate know too. If he doesn’t want to set a deadline and just will continue things the way they are, then he should understand why I don’t want and can’t be a part of his future. I don’t need any liabilities in my life, especially since this person is a complete stranger. If “possible” stardom is more important, I hope to be more important to someone else, someday.

      1. anonymousse says:

        Possible stardom is ALREADY more important.

        And he’s rude to people who are actually less fortunate to him, what a guy!

        The money is gone and he’s fine with losing more.

      2. Really, after writing that all out, do you not see that your boyfriend is really messed up and that this isn’t going to change? Even if the roommate were eventually out of the picture, the real issue here is your bf’s character. It’s not the roommate. This is a situation of your bf’s creation. Plus, a guy who never ever gives money to homeless people (or buys them a burger, say, if they ask in Wendy’s) AND fucking yells at them to get a job… honey, that’s not a good man. It isn’t. Please move on from this.

      3. Also: You call the roommate a loser, idiot, con-artist, etc. But seriously? Your boyfriend is the loser, idiot, and con artist! You say he’s being taken advantage of and strung along with promises of fame. Well, you’re being strung along with talk of marriage, and you’re paying for stuff and giving up things you want, so I’d say that’s being taken advantage of.

        You’re projecting everything onto the roommate, but you’re not seeing that the same dynamic is playing out with you and your bf, and that he’s actually the problem.

      4. You tell him he’s picking Stardom over you, you tell him to stop talking to you about the roommate but he doesn’t… you keep drawing lines in the sand which he continually ignores. Grow some ovaries and dump this loser. He doesn’t respect you. If he did he would’ve responded to your statements instead of ignoring them or turning it around on you.

  21. From all the changes in address, to all the leaching, to no reports of his current involvement in work/contacts involving showbiz, LW provides zilch evidence that bf’s roomie has any ability to help him get into the business. That is very strange given what she says is her bf’s obsession with this.

    1. So I read an article awhile back (maybe linked from Friday Links even!) about a guy who is like a serial squatter– moves in, stops paying rent, and by the time the roommate gets fed up, its been long enough that he has squatters rights and its a huge legal battle to evict. Then he moves on and does it again.
      This basically sounds like the same situation, but the boyfriend doesn’t care enough to get fed up. The longer this goes on, the worse it gets legally… LW should definitely not move in or get married or in any other way entangle herself in this situation, which is going to get much worse before it gets better.

      1. That was indeed a Friday Link a few months back, and I thought of it as I answered this letter.

      2. It also has shades of the bloke who kept failing the bar exam.

      3. Exasperated-original poster says:

        I have been trying to locate the previous post you are referring to about the squatter. Can someone point me in the right direction or post the link for me? Thanks!

  22. If I was going out with some guy and he yelled at a homeless person to get a job and gave me a bad time for giving a homeless some money or a subway sandwich I can’t tell you how fast I would be out of there.

    1. wobster109 says:

      I’m puzzled what this has to do with anything. LW isn’t asking her bf to yell at a homeless person, nor begrudging anyone a sandwich.

      She’s asking her bf to live together, and he presumably said yes since he told the freeloading roommate he “might” need to move out. He refused. She’s asking her bf to pay for some of the stuff they do together. Instead the boyfriend chooses to give $2k to the freeloading roommate, leaving her to shoulder the entire bill for their dates.

      I mean, there’s giving a homeless guy “some money”, and then there’s giving a self proclaimed “millionaire’s son” 2000 dollars while telling your girlfriend that you’re too broke for dates. Being civil to homeless people doesn’t require housing them, free of charge, forever. She’s not asking him to yell at a homeless guy, merely to set boundaries and tell him no.

      On that note, I would definitely give my partner a “bad time” if he gave a homeless guy $2000.

      1. @wobster, Oracle is responding to the LW’s update where she says her bf yells “Get a job!” to homeless people and gets mad at her for giving them money.

    2. wobster109 says:

      Whoops! Never mind anything I said above. I didn’t see LW’s follow up. You’re completely right.

  23. Bittergaymark says:

    Stardom. What a fucking idiot. Its amazing how idiots alway get other idiots to fall in love with them. Yes, LW. That second idiot… is You.

  24. The boyfriend does NOT love or respect you or himself. He respects the non-paying roommate more than you and he is a moocher, taking your money rather than being the man. The roommate may have done you a great service by exposing the true character of your boyfriend. Emotions hurt but losing everything you have will hurt more. If you stick with the foolish boyfriend, you will be more foolish than him. So sorry about the bad news.

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