“My Boyfriend Still Pays His Ex’s Bills”
Years went by and he continued to be miserable. So he went out and had a short-lived affair with another woman. Two years later he confessed feelings for me, and I also had feelings for him, too, but I didn’t like the fact that he was married. He separated and we began to date. He said I am the best thing that has ever happened to him. His kids, parents, and friends love our relationship; we are amazing together.
Although he’s with me, I feel he still cares for his ex. He gets nervous when she hears my voice when he’s on the phone with her because it upset her. It’s been two years and he still helps with her bills, including medical insurance, and he has left her the home and two properties that he manages for her (they have no children together, fyi). He says something inside of him tells him it’s the right thing to do.
He tells me every morning how much he loves me and that if he wanted her, he would have returned by now. Sometimes I feel like I may be overreacting. I’m feeling depressed and can’t sleep. But lately I’m beginning not to care anymore. I’ve had this feeling before, and soon after I move on. But with him I have held on. He treats me like a queen and loves my family and I love his. But why can’t he let her go??? Please advise? — Can’t Sleep
You mention that he separated from his wife and you began to date, but you don’t say anything about his divorcing her. Are they still married? If so, that begs even more questions, not the least of which is: why haven’t they divorced yet? If they ARE divorced, what kind of settlement was made? Maybe your boyfriend is legally bound to support his ex-wife for a certain duration of time. It’s not unusual for one partner to continue financially supporting an ex-spouse for the first few years following a divorce. I assume you’re familiar with alimony, right? Paying some bills and health insurance for some time and giving up a home in a divorce is pretty common and could be the “something inside his head” that’s telling him it’s the “right thing to do.”
If, however, your boyfriend is divorced and they have a clean break and he doesn’t legally owe her anything but is paying her bills for some other reason, then, yes, that reason is probably in direct conflict with the stability of your relationship. Whether he feels guilty for cheating on her and dumping her for another woman, or he still has feelings for her, or he is holding on to a little nugget of hope or possibility that they’ll eventually get back together, none of that bodes well for you and your place in his heart and life. But without more details, it’s hard to advise you beyond telling you to talk to him and continue pressing him for what that “something inside of him” actually is that’s telling him that supporting his (ex? estranged?)-wife is the “right thing to do.”


Thank you, Wendy, for taking a public stand against Trump and MAGA Republicans. I’ve been a reader of your column for years, and wondered about your political leanings, but never knew that you’d be so brave and strong. Thank you!
💜💜