“My Boyfriend Still Financially Supports His Ex-Wife”

My boyfriend was married to his high school sweetheart for 15 years until she left him four years ago. Soon after she left him and had her fun living the single life, she wanted him back. Luckily, he didn’t feel the same and decided to file for divorce. So, earlier this year, the divorce was finalized and he has to pay alimony for four years, and possibly half of his retirement if she sends the forms off to a lawyer.

She left him to be independent and to find herself, but she now realizes that she cannot financially support herself without his help. If there’s a vet bill, she calls him to help. A car issue? He comes by to look at it or to take it in for her. Hospital bills? He is paying for them. She does not know about our relationship because he doesn’t want to start drama. She can be very aggressive and will get into his business whenever she can.

Somehow, word got out that he had a female tenant renting out his guest room, and she freaked out and started yelling at him over the phone about not having any respect for her because it’s her house. Well, not anymore, it isn’t! And she is doing everything she can to get other people involved, and she almost got the tenant to leave by having her sister approach the tenant’s boyfriend to find out about her and if she was dating my boyfriend. Little does she know, he does have a girlfriend and it isn’t the tenant!

I have been with him for almost a year, but we have known each other for about three years. There is a 15-year age gap that has hindered the relationship when it comes to his feelings for me. He thinks I will be just like his ex when I turn 30 and get bored with the relationship and leave him for someone else. It’s unfair to compare me to his ex because you can’t generalize all women to be the same! I think he is the greatest, most caring and nurturing person I have ever met. I am willing to wait for him to take the next step and become something more, some day. It just hurts me to see him be manipulated by his ex!

I am not the only one to express concerns about it; his friends are more blunt about her scheming ways and he will agree 100%! He just says he feels bad for her and doesn’t like to see her struggle and he hopes she finds a new man to take care of her. So, I guess until then he will financially support her. I am afraid that he will continue to do this as our relationship progresses. I cannot be in a long-term relationship with a man who still cares for his ex emotionally and financially.

She left him. She wanted to stand on her own two feet, and yet he can’t let her do so without feeling bad. I know he loves her, but he is not IN LOVE with her anymore. I want to respect his decisions, but I can’t if he continues to do this throughout our relationship. How do I go about this without pushing him away? I love him, but if this is something he plans to keep doing, then I don’t see future for us. — Wish He’d Cut Ties

Eek, so many red flags here; I urge you to tread carefully and put the breaks on pursuing a long-term relationship. Neither of you is ready for that. He for sure isn’t emotionally available in the way you’d want a long-term partner to be available to you. I don’t think he’s really emotionally available for short-term either, unless you wanted to keep things super casual, and you don’t.

What makes him emotionally unavailable? Well, he hasn’t even attempted to set clear boundaries with his ex-wife. He doesn’t seem to have processed the end of their relationship if he’s jumping every time she needs something AND worried that you will be just like her. And he hasn’t told her – someone who seems very present in his life, still – about your relationship. No one who is truly emotionally available would do any of this.

Not only is your boyfriend not emotionally available to you, but also I don’t think you are ready for the kind of relationship you say you want. You actually don’t even seem to know WHAT you want. Just in this letter alone, you’ve made numerous contradictions about your intentions. On one hand, you say you’re “willing to wait for him to take the next step and become something more,” while on the other hand, you say “if this is something he plans to keep doing, then I don’t see future for us.” Well, which is it? Are you going to stand by him and wait however long it takes for him to be available for you or are you going to move on because you don’t like his behavior? Then you say that you “want to respect his decisions but [you] can’t if he continues to do this throughout [your] relationship.” Well, you either respect his decisions or you don’t. And you don’t. If you can only respect his decisions when they’re what you want or what you think is best, maybe your boyfriend is right to worry that you’ll be manipulative like his ex is.

Listen, it’s ok – it’s more than ok; it’s healthy and normal to set your own boundaries in a relationship. And if financially and emotionally supporting an ex (beyond what is legally mandated) is one of those things you won’t tolerate it, you need to communicate that with your boyfriend. But a boundary put the onus of responsibility on the person setting it. You say what you won’t tolerate and then what you’ll do if that boundary isn’t respected (and then you have to do the thing you say you’ll do).

You already know what your boundaries are. You list them very succinctly in your letter above. Basically, everything your boyfriend is doing for and to his ex is something you can’t accept. Now, your next step is to express that to your boyfriend and to tell him what you’ll do if the boundary isn’t respected: You’ll end the relationship. I know you asked how you can get him to stop his behavior “without pushing him away,” but boundaries don’t work that way.

Setting boundaries always comes with risk (and it’s why people – especially young people – have such a hard time setting them). You risk losing relationships you hope would work and offending people you care about. But the thing with boundaries is that if you don’t set them and you keep accepting and enabling behavior that you don’t like, you end up with relationships that aren’t satisfying with people you begin to resent. The irony is that in an effort to protect relationships that are important to you, you help create a dynamic that makes the relationship unsustainable and unrewarding. The irony is the risk of loss is far greater when you DON’T set boundaries than when you do.

Finally, I advise you to re-read this sentence you wrote: “There is a 15-year age gap that has hindered the relationship when it comes to his feelings for me.” Most times when people are in relationships with large gaps, they are quick to point out that the age gap doesn’t negatively affect the relationship or that they don’t even notice it, or they’ve managed to compromise on things that might be deal-breakers for other people. You don’t say any of that. You say the one thing that’s kind of a nail in the coffin of a relationship with a large gap: You say that it’s hindered the development of feelings.

If there’s a hurdle in a relationship that’s actually hindering the development of feelings – and for the record, I’m not sure your age gap is the main hurdle you two are facing – and it’s one that can’t be easily overcome, I don’t see much chance for a future together at all.


  1. The divorce might not even be final. Have you seen the paperwork for it?

  2. LW, you’re still in your 20s. You could be dating men without all this drama and baggage, but instead you’ve decided to pursue the emotionally unavailable 40-something with an “aggressive” ex-wife that he shows no real interest in severing ties from four years out. Why?

    FWIW, I dated a recently-divorced man for a year in my mid-20s and wish I’d run for the hills. The end of that relationship was kinda traumatizing.

  3. Avatar photo Moneypenny says:

    I get the feeling that LW can see the writing on the wall here, even if she’s not ready to accept it yet. I’m sure he’s a good guy, but there are just too many red flags waving here. I think she needs to extricate herself from this relationship because it’s really not going to get any better than what it is currently, that is, unless bf makes some real changes. And I don’t think that’s going to happen anytime soon based on what she’s describing.

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  5. The age gap is a serious problem. That he seems to still be in love with his ex (or is it current) wife is a bigger problem. That he seems to be suspicious of women in general seems to be the biggest problem. His ex left him when she turned 30? So she is at least a decade younger than him. He seems drawn to younger women he thinks he can control. The most generous interpretation of his on-going relationship with his ex is that he is treating her as if he is her father. Do you really want to marry your ‘new daddy’?

  6. PurpleStar says:

    I dated a lovely man who was recently divorced. We had an amazing relationship – except, his ex-wife was also very needy. Annual AC check on the house – he had to go and meet the AC guy. Car needed new tires he took it to the shop. Lawn mowing, new washing machine, sticky door lock – the list was endless. He still supported her financially – he could afford two households – and since I am financially independent I didn’t care. Except, when talking about long-term plans, things like living together, the deed on the home he lived in, and life insurance beneficiaries, he was resistant to changing anything. Um, sorry, if I was going to live with him and make a permanent life with him, I didn’t want his ex-wife claiming ownership of the house we lived in or being his sole beneficiary.

    And while he promised to “fix” it all and to ease back from the repairs and lawn care stuff, he didn’t He just began doing those things on the sly – when I was at work or out of town.

    I love that man. I do believe he loved me. I walked away.
    I found out a couple of years later that he had moved back in with her.

    OP – don’t waste your time.

  7. Been there. Done that. You *will* leave him when you’re 30 because you’ll realize he’s controlling, or emotionally unavailable, or some other huge deal breaker. He knows that and is unwilling to go it alone so will string out all the women he can to meet his emotional needs.

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