“How Do I Deal With my New Boyfriend’s Cheapness?”

I am long distance dating a man I met on Facebook through mutual friends. He is careful with money to a fault. He prefers I be the one to travel to him, which I don’t mind, but he doesn’t offer to chip in with travel costs even though he earns a decent salary. I have snow pent at least a few hundred dollars visiting him. When we were out shopping one day and I offered him about $3 for a box of candles I wanted as be was already in line, and he took it! However, I took my children to his home for a week and he happily bought all the food and a gift for them (while buying nothing for me).

He has suggested various things I should buy and, as I don’t have online shopping, he’s offered to order them if I reimburse him, which offended me and I told him so; either buy me a gift or don’t. His ex was financially abusive and he was buying all her groceries and her child’s clothes (child isn’t his). He has struggled to stop doing this. He admits he is still paying interest-free credit for her at $75 a month. I’ve said I’d feel happier if he just pays it off to end the soul tie to what was a very abusive relationship. He says this is financially controlling of me. I have pointed out the disconnect between his generosity to her and cheapness towards me. I’m due to visit him for a week in next month and am paying my children’s dad to have them; my boyfriend has suggested I take a train to his house this time so I am less tired than when I drive but he hasn’t offered to buy the ticket.

We have been friends for eighteen months, in a relationship for two. I want to get off on the right foot and feel we are arguing a lot about this issue very early on. He wants me to convert to Judaism, an expensive process, and has asked me to move in with my children and find a new job where he lives. He has also suggested I buy a Hebrew course and books as part of the process and said again as I don’t have online shopping, he could buy them and I could pay him back. Why was he so generous to his abusive ex who told him she didn’t even like him and yet is very cheap with me (but not so much my children)? How can we avoid falling out over money? — Tired of the Cheapness

Woah, way to bury the lede. You’ve been together only two months and are already discussing moving in together, converting to Judaism, and telling each other how and what to spend money on? These are such inappropriate conversations you’re having after only two months of dating. The cheapness is hardly the biggest issue here. You ask how you can avoid falling out over money, but what about falling out over religious differences, relationships with exes (or at least his relationship with his ex), caring for kids, maintaining a long-distance relationship, eventually merging two households, navigating the controlling tendencies you each seem to exhibit, and that little detail of maybe not even liking each other very much? Or do you like each other? You don’t mention whether you do or not, and that in itself is so telling. You’ve written 400 words about what you don’t like about the guy and not a single one about what you do. I’d say the relationship is pretty doomed from the get-go, and you’d save yourself a lot of potential grief just ending it now.

Also, how do you not have online shopping? What does that mean? If you have access to a computer and email, which you do because I have your letter to prove it, you have access to online shopping, no? And why are you paying your children’s dad to watch them when you go away? He’s their dad. I don’t understand.

Anyway, yeah: just MOA.

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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].

22 Comments

  1. I mean, all of this fast moving insanity is ridiculous, even more so since you have a kid, actually it’s just flat out wreckless but, why the hell does he need a van?

  2. And why are you paying your childrens father??

    1. Northern Star says:

      This is a small point, but it struck me, too. Her ex needs to be PAID to care for his own children? And she thinks THAT’S normal?

      1. I know my old bosses insanely, well insane, ex wife would often trade days with him (normal parenting stuff) but when she asked him to take a day he said sure of course. When he asked her she would figure out the monthly child support (15k you greedy brat) then pro rate it and charge him per day. I mean, she also charged him half of every single thing for the kids while they were with her. A banana, a bar of soap. I am not kidding. Some people are out of their minds and it’ll never change.

  3. Carolina Blue says:

    No LW, get your life in order and care for your children. Also please consider therapy.

  4. It is so complicated, just end it. Money is the least of your problems but you focus everything on this issue. Furthermore, you don’t even live at the same place, so why all the fuss? Give your children a rest and stay where you are. I am sure you can find a nice man there and meanwhile, be happy as a single mother.

  5. Avatar photo Skyblossom says:

    After only two months you have far too many problems to make this work. Why would you even discuss moving in together or religious conversion after two months of long distance dating?

    If you are this unhappy after only two months your relationship is doomed.

    Yes, if he can never travel to be with you because he needs a minyan then he should be paying half of the expense of you traveling to him.

    Do you really want to be with a guy who can’t travel away from his own area?

  6. You’ve been dating the guy for two months and are talking about CONVERTING TO HIS RELIGION? I’m not Jewish, but my understanding is that Orthodox Jews are strictly observant. It’s not just about where you go to church, it’s a way of living, and it will change many things about your day-to-day life, and will involve big changes for your children, too.

    Nowhere in your letter do you mention being called to Judaism, or feeling drawn to the beliefs of that faith, let alone to the specific beliefs and lifestyle of Orthodox Judaism.

    But this is all moot, because you don’t even like the guy and think he’s a cheapskate. So, long story short: don’t convert to a boyfriend’s religion if the relationship probably won’t exist by the end of the year.

    1. Anonymous says:

      She didn’t say he was an Orthodox Jew.

  7. Avatar photo Skyblossom says:

    I’m assuming that you would need to pay your ex for keeping the kids because you plan to travel during their time with you. The message your kids will get is that mom likes her boyfriend more than she likes them and if she has to choose the boyfriend or the kids she chooses the boyfriend. In the meantime dad is there for them. Your decisions determine whether your kids respect you or even like you. Ditching them over a new boyfriend will only harm your relationship with them. Kids very much judge you by your actions.

    Travel to visit him when it isn’t your turn to have your kids. When it comes to choosing between your kids or your boyfriend you should choose your kids.

    1. I don’t know what their custody schedule is like but it is NOT a huge deal to trade days to go on a trip. People do it all the time. ESPECIALLY people who do say Monday Tuesday w/ mom, Wed Thurs with dad, back to mom one day back to dad. It would be impossible for anyone to ever leave town for more than, well, travel time, if they never changed days. The kids will not be harmed from this.

      However in only 2 months the kids shouldn’t be aware of a BF anyway and she should be doing a TON of things differently anyway, but switching days with dad so she can do something for herself is fine.

      1. Avatar photo Skyblossom says:

        I doubt she is trading a Tuesday night for a Wednesday night. That would be a trade. She is leaving for some days and dad is keeping them. That would either be her weekend with the kids or they take turns by week and she is choosing to travel during her week.

        She should see her kids when it is her turn to see her kids and go see the boyfriend when she doesn’t have the kids. The exception would be if her ex never has the kids but I doubt that.

    2. Yes, that’s the message she’s sending to her kids, which is especially sad, because it’s very clear that she doesn’t even like her bf. She may be extremely desperate to have a bf, but it’s clear from the letter that there isn’t much about him that she actually likes.

  8. So, everyone’s covered the insanity of this relationship, but I’ll throw it out there that she “doesn’t have” online shopping because she doesn’t use or have a credit card and also either doesn’t have one or doesn’t use her bank card online. Maybe?

    1. Avatar photo Skyblossom says:

      That makes sense. I was trying to figure out how she wouldn’t have online shopping. Lack of a credit card will do that.

      1. Wandering Whimsy says:

        You can buy online with a debit card. 99% of my online purchases have been with a debit card because I try not to use credit cards. A person in 2026 with a computer that doesn’t have a debit card baffles me. How did she buy that computer? (Or tablet or maaaybe phone?) The only possibility I can think of is she’s living with strict parents or she’s part of a religious sect that wouldn’t like her converting to Judaism anyway or maybe she’s on bad terms with her bank.

  9. ele4phant says:

    After two months of dating – you have no standing to give input into his finances or how he chooses to spend his money, much less demand he spend more on you.

    There, we’ve solved that problem.

    Now go reckon with all the other problems you have with this guy, or more wisely, move on because it’s only been two months and this is already a shit show.

  10. anonymousse says:

    I don’t think you have a future with this man.

  11. dinoceros says:

    I agree with Wendy. Look, you’re presenting this as an issue where he’s this bonkers person and you’re just trying to have a normal relationship. Yet, you are talking about conversion and moving in with someone you’ve been dating for 2 months?!

    When you rush relationships, you lose all points of reference for how the relationship “should” work, including with finances. Most couples of 2 months would not have this many financial issues because this wouldn’t come up.

    Friends aren’t always compatible as a couple. You seem to have an issue with every way that he lives his life (and he apparently has issues with yours). Why not stop forcing it? Nobody with kids should ever be jumping in this quickly with someone they just started dating. (I dont’ think ANYONE should, but parents DO have to worry about other people when they make bad decisions.)

  12. 1. There seems to be some financial control issues here, and I don’t mean him.
    2. You have to pay your children’s father to watch them….whaaaat?
    3. You don’t have online shopping?

    Sometimes I think people write these letters in as a prank or something. I mean…really?

  13. Trust me when I say that money is not the issue here. I mean, sure, it’s one of many symptoms but not the root cause. You sound completely ill-matched, I strongly suggest moving on before you make changes that are very expensive to undo.

  14. Wandering Whimsy says:

    You are so incompatible with this guy it’s not even funny. You obviously don’t genuinely want to convert to Judaism because you care about its price tag. He’ll want you to convert genuinely even if he isn’t admitting that right now. You have very different philosophies on money. Money disagreements cause divorce. You understandably concerned about him sending money to his ex. That’s a red flag. He’s probably understandably concerned that you’re paying the father of your children to take care of them. He would understandably view that as a red flag. One could probably say you’re bad for each other even.

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