Men,

Throwaway account for obvious reasons. I’ve tried to make this post in other subreddits, but it keeps getting taken down. The divorced men seem to be the only community that understands. That said, please give me your advice for the following situation:

I’ve been divorced about 5 years. I’ve recently become engaged to a new woman and I’m having second thoughts.

Her positives are that she is genuinely interested in me, very sweet, we have common interests, and our time together is very enjoyable, she is reasonable, and we are able to discuss things calmly, there is no drama or fighting.

Her negatives are that she is very irresponsible with her finances, and the general trajectory of her life. She has $100k in debt. On top of that, when we met, she was gainfully employed, and has since quit her job. She’s been unemployed for almost a year. She quit due to health issues, hoping she could get them under control. Almost no progress has been made, and the health issues are not under control. There is no end in sight, and it is unknown if she will return to work. She still goes out and parties with her friends, goes to fun events, etc. But when it comes time to deal with life, her symptoms flare up. I don’t know what to think.

I’m stressed out and overwhelmed. I love all of her positive qualities, and I feel bad she is struggling with her health. I know she needs help, and I hate the thought of dropping her when she is having a hard time. But I just can’t take on a whole other person and their situation. It’s just too much for me.

Then I have my experience from my previous relationship and divorce, as many of us have. I was in a similar situation with my ex. She presented one version of herself to me, then flipped the script as the relationship became more serious. I was played like a fiddle for years. She refused to work and dumped everything on me. I stepped up to be the adult. She continued to be a dependent, refusing to grow up. My patience, generosity, and sense of duty were taken advantage of for years. So I’m having serious flashbacks, and there is a part of me that is literally screaming:”DON’T DO THIS AGAIN!”

I can’t tell if I’m overreacting or not. I need some outside perspective.

  1. Am I self-sabotaging by ending this relationship?

  2. Assuming I am not self-sabotaging, and acting in my best interest, how to I go about getting out of this situation?