I have to stop sending him money

We chat today.

Dear Meredith,

My self-esteem has suffered greatly over a problem I've had with my long-distance boyfriend of five years. He has had employment problems and professes not to be able to hold or keep a job or accumulate savings. He is from a very poor family, in which there are three young grandchildren to support.

Almost from the beginning, I have sent him money -- several hundred dollars at a time. I have now sent him over $10,000. All my friends and treatment team members have implored me to end the relationship but I cannot do so. I care about him and have no family of my own.

I must not continue to deplete my assets, but feel I'm being hard-hearted if I cut off the financial help. I am forming new connections online and am meeting people I want to get to know better, but feel I should end the relationship with the original boyfriend first ... but I cannot do it. I feel utterly conflicted and ashamed. Please help me!

– Anguished, Massachusetts

It sounds like you're more of a bank than a girlfriend. You must end this, and you seem to be ready.

I assume that by "treatment team" you mean that you work with mental health professionals. Keep those people around as you come up with a breakup plan. For the record, I'm not opposed to you sending this man a lengthy email explaining that you're done with the relationship and that you can't give him any more money. If it's easier to be assertive in writing, that's fine. He'll probably call after that, so you need to be ready for a confrontation. Your friends and team can help you practice saying n

You're allowed to be sad about the way this turned out, but don't feel conflicted. This man is a grownup and you can't pay for his life. It's time for confidence and self-preservation. Get this done soon -- like by the end of the month.

Readers? Are we missing something about the relationship? After five years, what does she owe him? Why is she so conflicted? Help.

– Meredith