I've been dating an amazing woman, Caroline, for about a year. We're both two years removed from our respective divorces to crazy exes, and we have an amazing relationship. We've started talking seriously about where our relationship is going and we agree it's perfect in every way. But I have one nagging issue ... she still supports her ex-husband.
Caroline and her ex used to manage a complex-yet-successful business as a husband-and-wife team. After they divorced, they maintained a decent working relationship. But he's scatterbrained, impulsive, and disorganized (one of the issues that led to their divorce). So during their marriage she managed his finances, business affairs, and some of his personal affairs. And this has continued to this day, albeit to a lesser extent than when they were married. She claims that "it's in the best interest of the business." †
Recently she told me how she voluntarily transferred $10,000 of her own money into his account to cover his bounced check. She has helped him organize his own medical care. He insists that they continue to pretend they're still married at work so the business owners won't be scared off. She doesn't like doing it, but reluctantly maintains that image.
I don't have any doubts about her feelings nor her level of commitment toward me and I'm not a jealous person. But it does upset me a bit that she still feels a sense of responsibility (business or otherwise) to care for her ex-husband.
Since I don't doubt her feelings or commitment towards me, maybe I shouldn't let it bother me ... but it does. Should I let it go, or should I ask her to stop supporting him?
– She's Supportive, Newton
A: Over time, this will be a deal-breaker. If you're going to have a future together, she must stop supporting him. She must also let her entire community know that they're no longer a couple -- and she has to split up the business.
Ask her about her long-term plan because she can't expect to do this forever. Offer to help her come up with a strategy for breaking free. She doesn't have to drop him tomorrow, but she has to have a timeline.
If she sees no way to change her situation or has no desire to try, you have to consider whether you can stick around. It's not like she's supporting a kid. She's pretending that her ex-husband is still her husband. You can't be expected to support him too.
Readers? Should he voice his concerns? What should he tell her? What expectations are fair?†