The Roommate Dilemma

Comments 33
Okay. So, probably not like 15 years ago.
Okay. So, probably not like 15 years ago.

I live unsustainably.

I’ve known it for a while, but it really became evident when I was kicking around how I might pay for expensive plumbing repair had any of my water pipes burst during a recent deep freeze and ice build up at my house which caused my water to stop running for two days.

A couple thousand dollars will really hurt given my current budget situation.

I know how pathetic that sounds.

But it’s true. I would need a credit card to pay for it. And I don’t possess any credit cards because I don’t want any more debt than I already have, and because I generally try hard to protect myself from myself.

Despite many, many cuts (and admittedly the undisciplined addition of a new car payment to offset some of the gains) since my ex-wife moved out nearly nine months ago, there appears to be more money going out than coming in. There aren’t many more nonessentials to cut.

First, there was a mortgage refinancing.

Then, a reduction in my mobile bill.

Then cuts to cable TV.

Then reduced internet speeds.

Day care costs less while my son’s in school, but that’s going to double over the summer, and that will be the end if I can’t figure something out between now and then.

The Options

I have some realistic things I can do to try and mitigate this problem.

1. I can earn more money. I’m likely to get a raise at work soon. I can work harder at my freelance-copywriting business (a huge challenge as a single parent 50 percent of the time). And I can try to find a higher-paying job altogether, though I am not eager to leave my current, stable position where I am treated well, and am already relatively well paid.

2. I can sell my house and move somewhere less expensive.

a. I don’t want to.

b. This is the only home my son has ever known.

c. I won’t make any money because I bought it at the top of the market and refinanced a couple times.

d. A very inexpensive place will be unsafe for my son.

e. A decent place will not cost THAT much less than what I pay now. How many months will I have to live in this new place JUST to offset the cost of moving? Maybe two years.

3. I can get a roommate. 

The Dilemma

After weighing all of my options for several months, this is the one that seems like the simplest, quickest fix.

I get a roommate. Someone to pay 40-45 percent of living expenses per month. That would provide the relief necessary to be comfortable.

Second to my mental, emotional, spiritual health, money—or a lack thereof—is certainly my biggest problem.

I want to solve it. Need to solve it.

But this is a problem, this idea. For many reasons. Here are some:

  1. First and foremost, I have a child half the time. A five-year-old son in kindergarten. His safety and security is my top priority. What stranger can I trust to live under the same roof as my child? The correct answer is: No one.
  2. I know exactly two people who I WOULD trust with my son and who I’ve flirted with asking. They are both recently divorced men like me. Ironically, both read this blog and will likely know who they are the second they read this sentence. One has a young daughter and lives a minimalist lifestyle. The other has two dogs and doesn’t need any financial help. They’re my two first choices. And still I haven’t asked either because there are still too many unanswered questions and too many doubts about whether they’d even entertain it.
  3. Not having any money to live life with OR having to sell the house is going to be bad for my son, too. I still kick around the roommate idea every day. What kind of a man would I let live in my home of eight years? Would we hang out? Be friends? Is that weird? Would I, or could I, ever trust him with my son? Do I want him having sex in my guest bedroom (which would become his room)? Do I want to consider him while planning my social calendar or time with my son? What kind of a woman would I let live in my home? What kind of a message does that send my son? The neighbors? My friends? Would I want to have sex with her? Would that be weird?

Yes. Yes, yes, and yes. It’s weird. A whole bunch of weird. And I’m always trying to do whatever the best thing is. In this instance, the answers don’t seem as obvious to me as they do with most choices I face.

I consulted my most trusted source for this sort of thing:


What’s Next?

I don’t know. I can do nothing and continue my slow descent into financial trouble.

I could potentially find another solution to the problem, but so far, I’m not coming up with any less-painful ones.

Should I start interviewing potential roommates? Do I really want to invite strangers into my home, advertising my possessions and the fact that I live alone with a small child?

Should I drop the entire thing?

I must make some financial changes.

A roommate (a good, trusted one) represents, near as I can tell, the simplest way to achieve my short-term goals.

I’d really like to hear from you guys on this one.

From parents.

From people who might have been in similar situations.

From people who have had good experiences with roommates.

From people who have had roommate nightmares.

If you have an opinion, I’d really like to hear it.

33 thoughts on “The Roommate Dilemma”

  1. Oh boy, that’s a tough one. I had a roommate once and I hated it. But I’m a private, introverted sort of person, so unless they’re family or I’m in a relationship with them, I don’t want to live with anyone else. Given your situation, and by that I mean, being in your mid-thirties with a young son, I don’t know…it just seems you’re beyond having a roommate. If you didn’t have a child, I’d say go for it. But you do. And that’s tricky.

    So, what are the alternatives? Can you get a part-time job working evenings and weekends when you don’t have your son? Would the thought of you having a roommate be enough to get your wife to agree to a reduction in support payments (assuming that’s part of your arrangement)? Could you trade in your car for something with more affordable payments?

    My final suggestion…and I already know you won’t like it…is to ask your Dad for money. From the sound of it, he is doing well financially and loves you and your son very much. I know he’s your hero, I know he worked hard and built his fortune from nothing when he was in a situation similar to yours, I know you are a proud man who wants to earn money, not have it given to him. But I’m pretty sure your Dad would do anything for you and for his grandson. He might even be proud to be able to help his family in a time of need. After all, what good is all that money if you can’t do good things for the ones you love (in other ways besides massive parties with kegs and expensive liquor)?

    Maybe you could help your Dad with his business from afar? Punch up the copy on his website, start a blog, manage his social media presence? Something so that you don’t feel like it’s a charity handout?

    Just thinking out loud. In fact, I just had another thought…what about becoming a gigolo? 😉 You need money and you’re celibate…two birds…one stone!

    KIDDING! Keep your chin up, man. I know you’ll find a great solution. Good luck.

    1. 1. I will not ask my dad for money. It’s possible I could look for ways to contribute to the company business and help from afar.

      2. Is there money in male prostitution, even if you’re just sort of average looking? Two birds, indeed.

  2. The ever continuing saga of roommates. I wish I could give you insight with your situation, but unfortunately I cannot. It’s to say that you are taking a sound approach.

    You don’t want to live in a place that would put your son at risk, but you don’t want to move to an area where you would move eventually and have that cycle continue.

    How about a scenario?

    Let’s say I was a contender for the spot. I’m single, almost 31, and trying to settle down and move on with his life. Many questions, including the ones you’ve brought up, immediately arise. However, being the live-in housemate, ***I’d have to abide by your rules*** (you own the place, and you know what you want). In return, I would hope that you would meet me halfway on a few things.

    I would have to prove myself as a worthy roommate with monetary issues, personal space, and cleanliness. I’d have to respect the time you have with your child and when he is over. I’m not one to throw huge parties, but I’d have a couple people over for dinner/movie/television some nights and a couple Sundays for football.

    Like any person: I’ll probably be having sex in the guest/my bedroom. However, as one looking to settle down, I’m looking for a respectable woman who wants kids. Being 30, many decent women probably do have children at this point, which I’m fine with. I’m not looking to bring rude psychos around. Of course, when your son is around it would be strange to have my date/girlfriend walking around and he wondering what the heck she is about.

    A goal in everyone’s life is to be friends with someone, but if this potential roommate is practically a stranger it will be weird at first. You can’t force a friendship, and you can’t force respect… the relationship will end up in a more strange bin than anticipated. However, communication is a must, and having a roommate who just walks by with no response to anyting isn’t really “productive.” You don’t want to room with a guy who is not personable. That will be boring, and it would get on your nerves.

    Of course, all people are different. I’m just trying to help with the objective, optimistic outlook. Best wishes!

    1. “Like any person: I’ll probably be having sex in the guest/my bedroom.”

      Christopher, I don’t mean to quibble with your statement here among several paragraphs of helpfulness… but…

      Hi, my name’s Matt. I never have sex. EVER. Nice to meet you.

      I am forced to rephrase.

      “Like any person not named Matt : I’ll probably be having sex in the guest/my bedroom.”

      Just wanted to clear up that minor inconsistency with the reality in which I exist.

        1. Ha!

          Sorry. Anyone who’s been around here knows I poke fun at my celibacy with great frequency.

          Don’t you dare apologize. Even if you HAD offended, this is a forum for free speech.

          As it were? Very sarcastic. I apologize for the lack of clarity. 🙂

  3. You’re overlooking a potential pool for your roommate search – women over 40 who have been in abusive relationships and just want to share expenses with sensible, responsible men who are not looking for sex. The situation sounds ideal (provided your housekeeping habits are up to par) for a woman who is just not interested in romance (no sex in your guest bedroom) who likely has grown children and thus knows what is and is not acceptable behavior around your son, who knows how to keep a house and a job and manage finances and is looking for a way to save money by sharing expenses. There are more of us out there than you might think.

    1. HA. Not to make light of your very astute suggestion. But what does that ad look like?

      “WANTED: Single woman over 40 fresh out of abusive relationship who I am not sexually attracted to and/or is not interested in sex herself. Prefer that you have grown children so that you know how to behave around young child.”

      That would be awesome.

      1. Hey, I’m not an ad writer! 🙂 I dunno. There are a lot of women like myself out there – I meet them every day. Seems like there should be a way…Maybe if you posted a picture of The World’s Most Interesting Man with “potential roommate in picture is just a representation and may or may not be the actual person you will be living with…” in small print underneath?

        1. WANTED: Formerly abused single mother of grown children who I am not attracted to and does not want sex. Must like children and grown men who pee-write their name in the snow.

  4. Oh wow. How much time do you have 🙂

    I have moved twice since my divorce in an effort to achieve a sustainable cost of living. I am now in a cozy two-bedroom condo with my youngest daughter, which was marvellously sustainable for about two minutes until my elest daughter got sick and had to stop working and now I’m paying her living expenses on top of my mortgage. >_<
    Fortunately my mom is also helping .

    When my ex and I divided our assests I got the house. But I let myself be held back too long by the thought that it was "the only home the kids had ever known." When I did make my move, the kids were old enough to kick up a fuss, but I put my foot down and reminded them that I was in charge, I was paying the bills, and therefore I got final say in where we lived. Of course I involved them in the house-hunting process, but it was an important learning experience for all of us.

    I bought a town-house style condo that worked well for us for a while, but then my eldest moved out, and then I started having huge problems with the number of stairs in the place because of my hip issues. One interim solution to offsetting the costs that worked well for us was that, after my elder daughter moved out, I enrolled in the Home-stay program at the nearby univeristy. I had two consecutive terms, each with a different home-stay student, both of whom proved very easy to live with. I chose the university home-stay rather than a simliar program for foreign high school students, becuase I didn't want the quasi-parental responsibilities that the high school program expected of the host. The second student would still be with us, except last June I moved again in order to ditch the stairs in time for my hip surgery — otherwise i would not have been able to recuperate in my own home.

    I certainly don't have all the answers — I am still, for all intents and purposes, living beyond my means (did I mention I also pay support to my ex?) But I learned a few things the hard way:

    1) Kids are resilient. People with kids move all the time. It's easy to beat yourself up about moving if the divorce is the reason for the move, but really it won't kill them.

    2) Be creative. In addition to the home-stay solution, I have bound a couple of ways to earn extra money over and above my day-job.

    3) Think about what you want to teach your son about managing money? Living within your means now might be the most important gift you can give your son in the long term. I'm still working on this one 🙂

    1. Thank you. There’s a ton here.

      I wish this were simpler. And maybe I’m just not smart enough to figure it out.

      But, near as I can tell, there is NOT a lot of money to be saved by moving somewhere else, but perhaps I’m wrong about that and need to investigate further.

      I can make more money. Maybe not a ton. And my writing will likely suffer. But that has to be on the table.

      Thank you for commenting, and reassuring me that it will likely be okay for the boy regardless. I hope so.

  5. In your situation and since you have a bit of time, start making an outline of what you expect from having a roommate. Pretty much all you covered are legitimate concerns. Most likely the roommate won’t make you suffer with his sexual noises, opting to go to his girlfriends home instead. However, it was a good thing to think about and whether you can stomach the thought when or if it happens. Explaining a roommates sexual visitors can easily be discussed by a breezy, “This is John’s girlfriend.” Five year old kids are pretty knowledgeable about the girlfriend/boyfriend thing and I don’t think once he is ok with you having a roommate, her addition won’t be a problem when she visits.

    More advice from the peanut thrower- make a list of the things that you expect, ground rules of sorts. Turn over every stone. Have in mind the age and financial stability your perspective roommate might have. When looking, having these honest evaluations in hand or at least in the back of your mind is helpful. Is your house conducive to blocking off the guest room to have a private or separate entrance? This could be particularly helpful if the roommate works late or holds after midnight outings every weekend.

    I had a roommate for a while after leaving my STBX. I won’t lie, the first month with a virtual stranger ( I met her at a church function and we were both looking) living in a small apartment was tough. As time went on, by the end of month two, we worked things out and are now close friends. Open communication is imperative.

    My last thought, use the interview process to your advantage. Think like a landlord, asking for a background check and financial proof of independence if dealing with a virtual stranger. Ask for multiple meetings and after you are sure about this guy have your son meet him before he moves in. Your son has to feel comfortable as well and having him involved even a little will help you decide if he is the right choice. Keep it business first from the beginning. A friendship can form later, but keep a firm line drawn at the beginning in case you have to kick him out. It won’t guarantee anything, however at least you know without a doubt you made the best choice possible for your situation.

    Best wishes on this decision,


    1. There’s a lot of good stuff here. A lot.

      Thank you very much for this.

      If I didn’t have a son… well, if I didn’t have a son, I wouldn’t even live here… but this would be a no-brainer. I do have a good house for having a roommate. Not perfect. But pretty good, from a privacy standpoint.

      I have a LOT to think about and consider.

  6. If you do choose to go with a roommate, put EVERYTHING in writing. Will he be expected to pay utilities, or are they included? Will you share food, or have separate shelves in the fridge? I’m sure you remember the drill from your college days. I have a few rental properties, so I see good situations and bad. A lease is a must! Do it on a trial basis to start out. Make your expectations crystal clear–and again, put them in writing and have him sign. Good luck to you! 🙂

  7. I feel for you Matt. I am juggling the same situation. Do I get a male roommate or do I get a female? Will they try to rip me off? Will they be able to tolerate the comings and goings of my 2 sons, 1 which lives with me 1 which doesn’t, and my cats. Will they be able to tolerate my noise and I, theirs. It’s hard isn’t it. I have lived with people before, at one time there were 9 of us in one flat. That was interesting, and sometimes fun. Most of the experiences have been positive. Maybe go with the people you know first and go from there. The above comment has some good ideas too. Lay down some ground rules from the beginning. We lived with a roommate in an already established flat with our kids to save money and he ended up moving out. One of our sons is quite a mischievous one and he would tell him off and I got territorial, so someone who understands children would be good. Early childhood teachers would be good too, (don’t know if you have those over there). Also, having the company is good. If I think of anything helpful I’ll post it for you. I’m nervous about this too. Good luck Matt 🙂

    1. To be sure, I HATE everything about this idea except the part where I’d have a lot more money laying around.

      But, yes. You bring up all kind of real-life stuff.

      I’m just going to keep thinking about it, talking about it, asking questions. See what’s up.

      Please do keep me apprised of how it’s going for you. 🙂 Good luck to you too.

  8. Matt,

    As a mother who divorced when my son was 3, here are my thoughts on the matter. I understand that you are in a financial predicament and also understand your not wanting to move or sell your home. Children do better with stability.

    As far as the roommate situation goes – great idea IF you three (son included) can get along and your roommate is mature and won’t be bringing unwanted issues into the home. Also, I highly recommend you choose a male and not a female. Having a female living there, in my opinion, would cause too much confusion for your son. It may also bring about many more complications than you need to bother with. That could include a wide range of complications.

    Furthermore, no matter what you tell your ex, how you explain your living arrangement to her, all she’ll see is a woman living in your home. That alone could cause many unnecessary problems. I say keep it simple by finding a male roommate who you can trust and get along with.

  9. How great would it be to find a roommate that travels for work or has a significant other whose house s/he often stays at. Maybe someone that just needs a crash pad. It might not be your ideal situation but if you look at it as something short-term (a year or two, tops) to give you a chance to catch up financially, then hell yeah. I dated a guy once who had a kid and roommates. His kid seemed to enjoy the situation – one more “friend” to talk to.

  10. Do you live near a university or college? I’m thinking of renting out a room to a grad student. They are hungry and responsible types, usually. I know cash is king, but maybe they could help with household tasks?

  11. Hi Matt,

    I found your blog because it’s basically on the front page of WordPress today. I haven’t read many of your posts. Take everything I say with a jar of salt. But here are some things I might do in your shoes:

    The thing someone mentioned about seeing if you can do work for your dad’s company is a good idea. Especially if it helps you build up a portfolio of online work that you can leverage to get other clients.

    The other thing alluded to, about flipping your mindset from saving more money to earning more money, is also an intriguing possibility. If you do try to take on extra work, could you make it work that you do for yourself, that you enjoy, that is designed to generate income streams (even small ones) in the future? Writing an ebook might be a thought. Or learning a skill that can be done for anyone from anywhere, like contract app programming etc., and also can be done for yourself when you don’t have assignments.

    If your local/state zoning laws allow it and you live in a reasonable sort of destination (college town, near a company headquarters, etc.), you could consider using Airbnb to find short-term renters for the days your son is not living with you. You can search your town to see what is already out there.

    Anyway these are just a few thoughts I had and thought I’d share.

  12. Hi. I’m up after the kids (and my passed out drunk ex-fiance) went to bed. I’m very tired so this might turn into rambling. Honestly, I’m feeling really scared and alone right now and I don’t know what to do. MAJOR POINT: I’m searching the internet for ways to obtain affordable housing or another single mother in a similar or slightly better situation. No, I don’t trust anyone with my kids. The one person I trusted was my fiance, G, but she got drunk (AGAIN!) and hit my 4 year old daughter because she was crying. I’m done with G. Seriously. I’ve given her so so many chances. My children deserve better (my son is 7). I deserve better. The problem is that I can’t afford to leave. I just started working as a pharmacy tech. Part-time. But I’m scared about what’s going to happen in the summer…I CANNOT afford childcare, and I don’t trust anyone. Especially daycares…I hear about and read horror stories all the time. I’ve volunteered in an ER, and have seen way too many children come in– followed by a cop with a rape kit. Hell NO!!!! I don’t know what to do. I’ve never felt more scared and alone. I’m not sure what to do. I’m one class away from graduating with a B.S. in Cellular and Molecular Neuroscience and I’m trying so hard to make that class happen this spring, but because I can’t take anymore from my fiance, I don’t know if that’s going to happen. I took the MCAT in May, but I didn’t apply to med school because I don’t want to be $500k in debt, and I’d like to have a life and enjoy my beautiful babies. So now I want to be a Physician’s Assistant. Better hours. Less school. Less debt. More happy. But now how am I going to make this all happen for me and my kids? I had a life plan with G, but she effed that up!!!!!! I’m not even angry. What I am is DISAPPOINTED. And sad. Very, very sad. I have to pick up the pieces all by myself and dust myself off and hold on tight cuz life is going to get crazier on me. Wish me much love and much luck. I wish I could be that roommate to help you and your son keep your home. I wish I could just dump a bunch of money on your front doorstep. I’m so so sorry for your situation. Virtual hugs to you and your son, from myself and my kids. I hope everything works out.

  13. What did you do? I am in a very similar situation, and I’m concerned about keeping a consistent environment for my kids.

    1. I would have let my younger sister or one of my single best friends (there was only one and he’s remarried now) move in, but a stranger?

      I just couldn’t go there.

      I’m in the same house. Still just me and my son half of the time. I had a side-hustle consulting gig for a while that made it work.

      I stopped doing that so I’ll probably be worried about this again in the next 3-6 months. Derp.

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