I started going on dates with this guy (we’ll call him Jack) when I was 18 and a freshman in college. He was 19 and a year above me. I was very different back then as I had lived an extremely sheltered home life. We only went out four times, but before it could get anywhere I cut him out of my life due to fear of intimacy. I told him I didn’t like him, but truthfully, I didn’t give myself the chance to see if I did. We still remained friendly with each other. A few months later, Jack invited me out again. I decided to go out of curiosity. It was a little awkward to be honest, and afterwards we mutually decided to go our separate ways. He eventually had a girlfriend and I found someone too.

About a year later, he texted me asking if I would still be interested in trying things out. I told him I wasn’t. I was going through a recent breakup, and I knew I wasn’t in the right state of mind to go out with anyone. I didn’t tell him this. Then he sent me a long message about how he regretted losing me. I found it odd because I thought we both agreed we wouldn’t work out. I ignored it and moved on with my life.

It’s now been two years since our first time dating. I’ve definitely changed some since I first started college and I’m at a good place to try something new. Yesterday, Jack messaged me again. It was random, but I thought it over, and decided to reply. We got to talking some and he wants to go out for food to catch up.

Before I get in over my head, I wanted to ask for some advice. Is reconnecting with him worth it?