Shortcuts: “Does My Cross-dressing Fiancé Want to Be a Woman?”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go.

Is there a way to figure out if my cross-dressing fiancé wants to become a woman? I love him but need a male. Can you help? I think he wants to be a lesbian. I like his penis. — Needs a Man

The best way to find out if your cross-dressing fiancé wants a sex change is to ask him. Even if he does, there’s a strong possibility he’ll hang on to that penis of his that you like so much. Would you be ok dating/marrying a lesbian with a dick? (Some women might consider that the best of both worlds, you know). On the other hand, he’s probably perfectly happy being a man who likes to slip on a gown from time to time. Just ask!

My boyfriend bought a house in which the mortgage is approximately $900 per month. We have two roommates who contribute $500 each, plus utilities. Up until this point I have not paid rent but paid for all groceries and lawn care, and I cook and clean. He now is requesting I pay $500 per month in rent. Does this not make it seem as though he is making money off me? I am angry, upset, and, most of all, confused. I have always been very generous, contributing large amounts of money to home improvements. I feel as though now I am being completely taken advantage of. He is basically pocketing my $500 per month. — Girlfriend Not Tenant

Well, making a profit is kind of the point of being a landlord and charging tenants rent. You just didn’t realize you were your boyfriend’s tenant. Obviously, a conversation about your relationship and your living situation is long overdue. If you don’t think you should have to pay anything toward rent, explain why. But don’t be surprised if your boyfriend decides that paying for the groceries and doing the cooking and cleaning isn’t “paying your way” enough. It sounds like what he’s looking for is more than a domestic partner, and, indeed, a tenant and roommate he can make some money off of. If that doesn’t sit well with you, it’s probably time to look for a new place to live.

I have been in a relationship with my boyfriend for seven months now. I am having difficulty with understanding my sexual orientation. Before him, I was in a long-distance relationship with a girl. I consider myself bisexual, but I’m uncertain. I am wanting to experiment and find out if I’m completely bi, lesbian, or just straight. But I don’t know how to do that if I’m in a relationship. I told my boyfriend that I was attracted to both genders but in different ways. I fall for a guy’s personality and emotions, but with a girl I fall for everything. I am happy in this relationship, but I still feel like something is missing. Until I figure out my true orientation, I’m always going to feel like I’m stuck between a rock and a hard place. What do I do? — Unsure of Orientation

Regardless of what your sexual orientation is, if you’re in a relationship where you feel like something is missing, you are not entirely fulfilled, and you want to experiment with other people, regardless of their sex, then you probably should end your relationship. Your boyfriend isn’t doing it for you. Maybe that’s because he’s a guy and you aren’t truly into guys, or maybe you just aren’t into him. Either way, it’s time to MOA and give yourself the freedom to do the exploring you want and need to do.


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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. Avatar photo Raccoon eyes says:

    Woohoo for Shortcuts on Friday! Nice answers, Wendy!
    I really have nothing to add here….except LW1, if you are ENGAGED to this man, you need to be able to have CONVERSATIONS with him about, well, pretty much everything. And you dont seem to be, so please DO IT. It is in your best interests, his best interests, and your relationship’s best interests.

    1. RedroverRedrover says:

      Totally agree. I can’t imagine getting engaged to someone when I had this major of a concern!

  2. LW2 – If my boyfriend expected to make a profit off of our living together, I would be looking for a apartment so fast his head would spin. My relationship is not a business transaction.

  3. Yeah, WWS.
    Also, I really want to know how long LW2 has been living there with no expectations of rent. But yeah, like Wendy says, it brings your relationship from live in partner to tenant/roommate. I also wonder if this conversation was brought on by the boyfriend’s discussion with another roommate…

    1. ALSO, this reminds me, it’s a weird situation when you move into a place your SO owns. As opposed to a place you’re renting together, which can have its own complications, but not as much. These are things that need to be discussed before moving in together. A contact, even an informal one, can be very helpful in spelling out specifics in these situations. No one likes being taken advantage of (on either side of the equation – maybe in this situation the boyfriend’s felt like he was taken advantage of and decided collecting rent would make him feel better), so a contact helps everyone.

    2. I think it’s sort of an interesting question what a fair solution in LW2’s case would look like (and you might be right that the other roommates are resenting that she doesn’t have to pay rent).
      On the one hand, charging a live-in partner rent when you don’t really need the money seems a bit odd, on the other hand she’s basically saving the rent she would otherwise be paying for an apartment or room, which is a pretty big benefit – so in a sense she’s the one making money off him at the moment. Just because money isn’t changing hands doesn’t mean she’s not benefiting. Plus, her boyfriend may not be aware that she thinks of cooking etc. as something she does in exchange for living there for free.
      I would probably try to come up with some sort of compromise with her paying at least some rent, but not as much as the other roommates. Also, whatever she’s been contributing to the groceries should figure in the overall calculation as well.

      1. RedroverRedrover says:

        Totally agree. Personally I wouldn’t be comfortable with living with a boyfriend and not paying anything. Then you’re just taking advantage of him. Plus he has other expenses like maintenance and property tax, so he actually might not even be making money off her in the end. Plus he put a downpayment into the house, which he could have used to invest in something that would have greater growth, so he’s got an opportunity cost there.
        I think that what they should do is sit down and look at the costs of the place with no renters (include property tax, maintenance, insurance etc). And then figure out what a fair split would be. This will be the hardest step, because she shouldn’t be paying half (IMO) because she won’t be the one getting the asset in the end. She should maybe pay a third or something.
        Then add in all their other expenses like groceries and lawn care. Don’t forget expenses she doesn’t mention, like internet and TV. Maybe he’s paying those and they equal groceries and lawn care, who knows. Anyway, figure those out. Then talk about the split of work. If she’s doing all the work around the house, maybe she should stop and they should split it equally. Or maybe he should pay for some of the other expenses like groceries in exchange for that. Whatever works for them. Now they’ve got the basic costs that she should pay and he should pay.
        Then take into account the renters. They both have to live with them, so it’s not fair that he’s the only one who gets to benefit financially from them. I would say if they split the housing expenses 2/3 to 1/3, then they should split the rent income the same way. So he’d get $667 off his expenses, and she’d get $333 off hers. Aaaaand they’re done! I imagine she’ll end up paying somewhat less than the renters in rent. He might be pissed though because he might end up still having to pay something. But, tough. He shouldn’t get to live for free off her, just like she shouldn’t get to live free off him.

      2. That’s a good way of thinking about it. If you take the roommates out of the equation, then LW2 would probably contribute to the monthly mortgage payments (though, like you said, she shouldn’t be paying half, since it’s his house). If she’s contributing to those payments, however, then it’s also logical for her to receive a proportionate amount of money back if they have tenants. I guess I like this way of framing it because it doesn’t assume that the boyfriend treats LW2 like a tenant (in which case he might try to just get as much rent as possible from her, regardless of how much he pays for the mortgage), but it also doesn’t ignore the fact that LW receives a benefit from living in the house.

      3. RedroverRedrover says:

        Exactly, the renters are just confusing the issue. I imagine her bf is realizing how expensive it is to own a home, and is thinking it’s not fair that she pays nothing towards it. He may not really realize what she spends on groceries etc. And he has a bunch of expenses that she’s not taking into account; he might actually be paying more than her at this point and he’s feeling like a chump. So they should sort all that out first, just like any other couple would.

    3. If I were one of the roommate, I would like to see the LW pay rent, that’s for sure ! I lived with a couple once, where the girl owned the house, her boyfriend lived with her and I was renting one room. You bet that we were splitting utilities in three, not in two. From my point of view it was “I’m sharing this house with two people, not with one”. If I’m paying to have access to a kitchen, the boyfriend/girlfriend should pay to have access to the kitchen. If I’m paying to do my laundry in the house, the SO should pay to do their laundry too. Otherwise she’s a guest in the house.

      1. Oh and if I were the LW, this would be my compromise: if the mortgage is $900, let’s split it in three, and instead of two times $500, ask for three time $335. This way the LW is paying rent, it’s fair for the roommates and the boyfriend is not making money off her back.

      2. Yup, agree completely.

  4. I wonder LW2 if you guys discussed splitting finances at all before you moved in? Perhaps sit down with him and add up all the household expenses. Utilities, mortgage, any insurances, groceries, lawn care, maintenance funds, etc etc. And figure out what you together would think was a fair way to split. I wouldn’t doubt though that the roommates might be starting to get irked that you two seemingly aren’t actually contributing to rent? If you want to keep those funds coming in, finding a fair way to split the finances related to the home are probably definitely in order.

    1. If the roommates are pissed tat she isn’t contributing as much as they are, then they re assholes. She is his live-in girlfriend, not a tenant. I presume she is sharing a room with her bf, she doesn’t have her own space. She pays for all lawn care and groceries. That alone is probably well over $500. If they want to add up all expenses, minus what the roommates pay, and then split the remainder, that would be fair. But I he’s expecting her to just fork over $500, to his profit, then she needs to get the fuck out of that house.

      1. I mean they’re roommates of course they’re concerned that they’re getting a good deal! They have to care about themselves to some extent. If they aren’t getting a good deal, then they need to know it’s time to look elsewhere. We don’t know that what she pays is on par with what he does. Which is why it’s always good to COMMUNICATE. I didn’t say she should just fork over $500 a month without discussing it. But, to you know talk to him about it. Which seems like is something that they skipped in the first place or they probably wouldn’t be in the position they are now! And I mean live when people move in they split rent. And usually if they want things to work and for everyone to feel like they are on the same page they discuss it. And don’t assume that paying for groceries and lawn care makes them even. I mean it’s on both of them for not discussing it, but I mean if she wants to forego discussing it and just assume he’s an ass then she should just move out.

      2. I apparently like the phrase I mean today!

      3. They definitely need to talk about it. I just don’t think that the tenants should have anything to do with it. Frankly, it’s none of their business how Bf and LW deal with their finances. If they don’t like that they pay rent and she doesn’t then they need to move out. LW and her bf should have discussed all this before moving in, but they can’t unring that bell. And she says she pays for ALL the groceries. For 4 grown adults that’s a lot of money each month. They need to sit down and have a chat. But I still believe that if BF is expecting to make a profit off of her, then she needs to move out.

      4. We can only assume she pays for the other two roommates groceries. Saying all could mean just her and him. And I’m sorry but yeah if I was a roommate in a house and realized that all of the tenants weren’t paying the same amount I would definitely say something and then I would leave. I mean obviously it’s the renters choice to charge what they want. But, it’s a tenant’s choice to realize they aren’t happy with the situation. Maybe they feel just as used! And honestly we don’t know that bf is expecting to make a profit or not based on this. Because, she according to the letter hasn’t spoken to him. I mean paying for a household doesn’t end at the mortgage payment. Tv and cable and electricity, gas depending on how they heat the home and cook, etc. Can add up to a ton. Which I mean I’m just baffled that you move in somewhere and just assume that groceries and lawn care equal it’s all good without actually discussing it. People amaze me.

      5. I agree to an extent. If I were a tenant I can see being upset, but at the same time, is she a tenant or live-in girlfriend? They need to talk and STAT.

      6. And I’m not saying that the bf is expecting to make a profit off of her, just that IF they talk, and IF he is, then she needs to move out.

      7. RedroverRedrover says:

        If I were a roommate I wouldn’t count my landlord’s girlfriend as a tenant, and I wouldn’t expect her to pay the same as me. The only thing I need to know, as a roommate, is what the living situation is, and what I pay. If $500 for living with one couple and one single seems reasonable to me, then I’m happy. If not, I go somewhere else. It’s none of my business how my landlord and his girlfriend deal with their expenses. The landlord owns the house, he gets to set the prices. I have no say, except for whether I stay or go.

      8. Well no you have no say but you’re allowed to have an opinion. Which I mean I probably wouldn’t actually say anything to the landlord. I would just move. And if they asked I would say, I feel like I’m paying for more than my share and I can get a better deal elsewhere.

      9. RedroverRedrover says:

        I just don’t get why you think they’re all equal roommates. If we were all renting a house together, then yeah, definitely I would feel the way you describe. But if someone owns a house and I’m renting a room, then I wouldn’t assume we should all pay the same. Why would the landlord have to pay the same as a renter? The whole point of being a landlord is to have to pay less. And he’s free to let anyone live there for free if he wants, it’s his house. I’m just renting a room, and if the going rate in the area is $500, then that’s totally reasonable. It has nothing to do with the total expenses. It’s the market cost of renting a room. I shouldn’t get a discount just because he has people living there for free.
        I mean, my parents rented rooms out when we were kids. There were my parents plus five kids. There were two people renting rooms. Are you saying my parents should have had to pay 7/9 of the total housing cost for it to be fair? It wouldn’t even have made financial sense to rent the rooms. They just advertised them at a monthly rate, the rate was inline with the market, the renters were aware there were 5 kids there, and that was that. I imagine the rate was actually lower than market because of the 5 kids thing, but regardless, it certainly wasn’t 1/9 of the total expenses.

      10. Honestly we just have very differing opinions on this and it’s not worth discussing with you. Because, no I don’t think that I they should pay 7/9 of the housing cost to be fair.

      11. No because kids are dependents and can’t earn any money. That’s a totally different situation. If I was renting a room while raising a family I would just charge a flat rate. It becomes WAY too complicated when there is a family involved.

      12. That’s assuming you’re getting a better deal elsewhere. I would assume that the roommates were not previously friends with the boyfriend, and that he’s charging the market rate to them.
        Also I know plenty of people who had a place and looked for a roommate and charged them a fair market rate which was more than what they were paying. It sounds like that is something you would object to once finding out and move. But if you’re also getting a better deal than you would at another place, then you’d have to decide whether it’s worth it to pay more to know things are paid for equally. (This is taking out the significant other from the equation, of course.)

      13. Sorry, left out the detail that these friends were renting and doing this practice. It’s actually fairly common around here, particularly if the place is rent-controlled and/or they’ve been living in the same place for a while.

      14. I don’t think it’s a fair split. Like I mention below, there are SO MANY gray areas because her contribution is to household expenses, which the boyfriend should be paying and should be responsible for. A couple is two people. Period. It would be one thing if they were living with another couple and they split everything down the middle, but they’re not.

      15. Agreed.

      16. I think the biggest problem with me is utilities. In the summer, I don’t even put a/c in my apartment because I don’t care about the heat. When I lived with a couple, the girl would always put the a/c to something crazy like 65F when it was 100F outside. And then we would “evenly split the bill” at the end of the month. I would have been pissed in the utilities were split in two instead of three because they are a couple !

      17. RedroverRedrover says:

        If it were me owning the place, I wouldn’t charge for utilities. I’d just charge a monthly rate and figure out the utilities on my end. If LW’s boyfriend isn’t doing it this way, then yeah, obviously they should all split the utilities.

      18. In the letter, the LW said “plus utilities” but that could mean anything from a flat rate each month to splitting the bill each month. Not to mention which utilities… is it just water/gas/electric? Or does that include internet and cable?

      19. For personal expenses, yes it isn’t the tenant’s business. But with everything else, since the tenants live there I would assume they want it to be fair and everyone contributes equally. It’s really bizarre that the LW is paying for all the groceries. When I first read it I thought it was just her and the boyfriend but reading it again I think she’s contributing to EVERYONE’S grocery bill which personally I think is ridiculous — give everyone a cupboard to put their food in and they are responsible for their own food.

      20. I think where the line is gray though is that she is paying for some of the expenses on the house. That is the landlord’s job, not hers. I get that she’s contributing BUT at the same time she needs to reconfigure exactly WHAT she should be contributing. The boyfriend’s job as the landlord is to keep the house in working order. That includes lawn care, electricity, utilities, plumbing issues if they come up, painting, etc. etc. Despite the fact that she is a live-in girlfriend, I think contributing rent money instead of paying for lawn care will solve this issue and make the lines less gray.

      21. actually utilities and electricity are covered by almost NO landlords. the rest is the landlord’s job. but, i agree that the whole thing could be fixed by just having a conversation and figuring out a fair way to split everything.

      22. Actually, I think that varies a lot more than you’d think. Having lived in 3 different states and 2 different countries, I can say I’ve never paid for water, sometimes paid gas, and most of the time paid for electricity. And Bassanio had lived in one additional country and one more state and had a similar experience. It really depends.

      23. Yup, I realize that, but at the same time in this case the landlord lives in the same house. If he put that all into the rent money — maybe increase each tenant by $50 — and paid it himself he wouldn’t have so many issues with splitting the expenses.

    2. I also have a problem with the fact that he just announced that she needed to pay $500 without sitting down and having a discussion about why he wants/needs the money, etc. Do these people even talk to each other?

    3. eelliinnss says:

      I think its absolutely tacky and disgusting if the tenants know how much the mortgage is on this house. You just DON’T tell your tenants what your mortgage is. If I was this landlord I’d let them assume the mortgage is like $1700 a month or something so they’d assume I’m contributing as well. The LW knows how much her boyfriend pays and so I assume the other roommates do as well, and ugh that’s just such a bad way.

      1. I’m curious, what would you think of a situation in which there were very low mortgage payments or even no mortgage payments at all (say, someone’s renting out rooms in a house they’ve inherited)? Should rent be reduced based on how much or how little the landlord pays for the house? I sort of think this isn’t required with tenants, with whom the landlord has a business relationship. He can charge the market rate and there’s nothing tacky about that. It’s different with girlfriend because it’s not a business relationship.

      2. RedroverRedrover says:

        Yeah, this was exactly my point in the series of posts above. Rent for tenants isn’t based on the cost to the landlord. It’s based on what the market can bear. If the market price is so low that the landlord doesn’t make a profit, then he should probably sell the building. If the market price is so high that the landlord is rolling in it, well, that’s how it goes. That’s why people invest in real estate.

      3. eelliinnss says:

        Um yeah, that was my point. He can absolutely charge his tenants whatever he wants and whatever they agree to pay. I just think, the smart thing to do is not to tell his tenants how much HE pays. It’s better to have them assume than to know for sure.
        I just think it’s tacky to talk about your mortgage in general, with anyone except your bank and whoever (if anyone) else is financially responsible for it.

      4. RedroverRedrover says:

        I don’t think the tenants know. The LW knows, but she’s his girlfriend, not a tenant (so far, anyway).

    4. The roommates are renting rooms from him. Its not really any of their business who pays what or who pays the mortgage. If they decide they don’t like the situation, they find another place to rent.

      1. That was my entire point. But, if you want to keep tenants then part of that means you have to keep them happy. Maybe one of the tenants said they were going to leave and when asked why they said they felt the rates or split were unfair and the owner decided it was worth keeping them and so he’s changing the rates. We really don’t know enough at all about the situation to know why he’s suddenly changing things. Which goes back to my point that the LW really needs to discuss this with him.

      2. Again, you’re assuming the roommates are privy to information about his mortgage payment amounts and what the girlfriend is or isn’t paying, which is not a thing to talk about with your tenants (even if they’re also roommates). The only other scenarios I see where the roommates would react in this way were if the girlfriend moved in after the roommates but rates stayed the same, or maybe they were all friends beforehand.

      3. Again I realize that, but my point is we don’t know enough to know what the background is. My hypothesis is just as possible as any other.

  5. Sunshine Brite says:

    LW2, how long have you been living rent free? I can see it since you say you contribute to improvements that he may be wanting to start an improvement fund if he sees a roof or something on the horizon. You two need to talk about this. Yes he’s making money on the tenants but I would definitely need mortgage plus part of the utilities to put up with 2 roommates myself.

    There are other expenses that might not be built in that he’s trying to build up like the taxes, mortgage insurance, homeowner’s insurance, etc. where your contribution would be going. You need to open up with him (somewhere the tenants can’t here) about why you’re changing the arrangement and what that looks like for his contribution too. Talk about your partnership and its place in this living arrangement.

  6. LW1: Going from cross-dressing to making the assumption your fiancé wants to be a woman is a big jump. Talk to him first. Most likely it’s a fetish, but I have a feeling that freaks you out. But you need to communicate about everything and either accept it or MOA.
    LW2: I think your boyfriend is kind of sleazy. I know he owns the place, but he lives there as well and makes his roommates cover the entire cost of the mortgage. If he didn’t live there that would be different, but it sounds like he wants others to cover things for him and now he wants you to pay up. I don’t think that’s a good quality in someone.
    LW3: So I don’t really see a problem with telling your boyfriend you want to experiment, but you should fully expect him to not be okay with that and then you have to move on to figure out what you want. I’m bi and I firmly believe sleeping with a bunch of people and playing around helped me come to that conclusion about myself when I was confused.

  7. LW2, I don’t think your boyfriend is being sleazy or taking advantage of you with asking you to pay rent. I think it was presumptuous of you to assume you could NOT pay rent in the first place. My suggested solution is that you pay $250. The other tenants are paying $500 for i’m assuming their own room, you are (i’m assuming) sharing a room with your bf, in which case you are only getting half a room, so half the price $250. I think this would please everybody.
    There’s no reason for you two to look at all of his expenses to figure out a “fair” split because at this point (not engaged, or married) i don’t think it’s your business. Paying $250 allows you to feel like your getting a gf deal (and i’m sure is way less than you’d be paying out on your own), and he still gets some income. I’d also suggest renegotiating groceries/lawn care etc. since you’ll now be paying rent.

  8. LW2: Have you and your boyfriend even talked about finances?? Yeah he owns the house, but when you moved in did you talk about how you’re going to pay for x and he’s going to pay for y? It’s high time you did that…it should have happened a looong time ago. Talk about how you pay for food, the mortgage — and how much you want total from the tenants — lawn care, repairs on the house, everything.
    I understand why you feel like he is doing a money grab because I would feel the same way if a guy did that to me without discussion. Yet at the same time I understand why he would expect you to pay rent…I’m not saying he handled this well because he didn’t handle it well AT ALL, but I can see it.
    Here’s an idea: since he is the landlord, he pays all the expenses of the house — upkeep, lawn, painting, fix-it-up type stuff, internet, cable, etc. etc. — with the rent money, including yours. After that, you then start talking about who pays for what in terms of your personal needs such as food, cleaning supplies, clothing, insurance bills, personal health bills, phone bills, etc. etc. Maybe you split it in half. Maybe you split it 60-40. Maybe you pay for some things and he pays for others. Whatever works for you. But keeping the house expenses up to him as the landlord would help a lot.

  9. LW2: I with the others that thinks your boyfriend is wrong. He already lives free and now he wants you to pay. What does he contribute to the household at all? I guess he pays the insurance and major repairs? The whole thing sounds weird. It would be nice to know what prompted him to ask this of you now. Was it his idea or a response to the roommates. You could pay the $500 and then quit cooking, cleaning, and paying for groceries and lawn care. This whole thing sounds totally unappealing. I think you need to have a where is the relationship going conversation.

  10. Wendy redeems herself after her dreadful advice from the other day.

    And just because some dude wears lady things doesn’t mean he wants to be a woman… though he is a bit freaky. I mean come on… I never let my girlfriend see my thongs.

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