Dear Meredith,

In short, I tend to overcomplicate things. I don’t have a problem meeting people and going on dates. I think dating is fun. But I’ve been taking a break from it for a few months after a run of budding relationships went south. Within that time, I began seeking therapy for depression. My therapist thinks I choose people who are somehow slightly unavailable as a self-preservation method so they can’t get too close. I think I developed this pattern after I found out an ex was cheating on me two years ago. I have had some great breakthroughs with this therapist’s help.

Back in March, I met a great guy, “Jake.” Jake is very sweet, family-oriented, attractive, smart, respectful, funny, and makes a lot of effort. At the time, I had just started seeing another guy (another Mr. Unavailable), and although I didn’t think the new fling was going anywhere, I couldn’t get him out of my head. I went on three dates with Jake and then made every excuse not to like him, from his shoes to average height, all because Mr. Unavailable was consuming my every thought. I texted Jake that I didn’t see us going anywhere, and he replied that he was a bit surprised but appreciated my honesty.

The relationship with Mr. Unavailable inevitably crashed and burned over the summer. A coworker convinced me to text Jake a few weeks ago, and we have been on a few dates since. I feel like my vision is so much clearer now. So much so that his bad choice in clothing and slight dad-bod condition doesn’t affect my attraction to him. I am slightly concerned about the fact that he jumped back in so easily. We text here and there and it’s usually just to make plans. I was honest with him about the past (that I was seeing someone else), and he said he’s really happy that I reached out again. I like him for all the right reasons (for once) and want to see where it goes.

Do you think I can continue to make the same progress with myself in therapy AND foster a potential new relationship at the same time?

– Over-complicating