My Ex Wants to Meet After a long break.. How Should I Play This? (Real Story)

Coach Mac,

I’ll try to keep this one to the point. I broke up with my ex two years ago, and now she’s come back and wants to go to dinner this coming weekend.

To give you some background: I’m 35 and she’s 25. I know it’s a big age gap and her maturity was a problem at the end. We were together for two years, and it felt like we were always fighting about petty issues. I was highly attracted to her, so I put up with it more than I would normally—looking back now, I see that two years later.

We broke up for a variety of reasons. One was that she didn’t have a job for six months and seemed content to leech off me. At first, it was okay, but then she got too comfortable not working and insisted on expensive things, which strained my finances. I make good money—always have—so it was manageable until it got out of hand. She would rack up her credit cards and then beg me to pay them off; the last bill was over ten thousand dollars. She was clever in her approach too—she knew exactly how to push my happy buttons. I put up with that for a while.

Another issue was that she’d sometimes dress provocatively, which embarrassed me in public. Finally, I’d had enough and broke up with her, citing her spending habits and her style of dress as major problems. She accused me of caring about money too much and said I dressed like a golfer. I am actually a golfer, so I wasn’t offended by that.

I did miss her a lot, and I even hooked up with her a few times after we broke up. But it was really over when I found out she had a new boyfriend who was even older than me—he looked about 45. In the last two years I stayed single and haven’t met anyone as attractive as her. So when she called, I was excited—and then I thought, “What am I getting myself into?”

We talked for almost an hour on the phone. She said she called because she had a dream about me but wouldn’t tell me what happened—she just giggled about it. She also brought up her most recent breakup, saying that guy was controlling and treated her like a child. I bit my tongue from saying, “Well, he could have been your father at his age.” She doesn’t know I saw his picture.

I’m going to meet her for dinner, but I wanted to get your take—how do I play this? I don’t think I want her back, but I’m curious. At the same time, I know her, and it doesn’t sound like much has changed. She also mentioned on the call that she hasn’t worked for a year (and giggled about it). I think that’s a red flag, but I still want to see her. Thoughts?