Dear Meredith,

After college, I met a lovely young man about five years older. He was working on his master’s around Boston, where I’m from.

After returning to Boston, we began dating and were together for five years. The first few were beautiful (we even lived abroad for a time), while the last two were confusing for me. He never expressed issues with the relationship, though I felt like we had reached a plateau. Looking back, I was quite disconnected from my emotions, a poor communicator, and unsure of my sexuality. I didn’t know what I wanted at 27.

When I broke things off, he moved out without a fight, though he reached out after a few months with a teary phone call. He asked if I had reconsidered, and, so shortly after the breakup, I hadn’t. A couple of years later, when I realized I wanted to try to rekindle things, he had already moved on with a lovely woman. The pain was real, especially the self-blame from having been the one to call things off. I was compassionate with myself, trying to be grateful for the time we had together and everything I learned from him about being a mensch.

I have dated and grown in the process, but have found no long-term prospects. I just finished a master’s in a field I enjoy, am involved in several community groups, am active, have several platonic friends, have worked on my family-of-origin issues, and can communicate my needs and take care of more of them myself. Still, I wish I could have another chance with the ex. He was one of the most intelligent, thoughtful, funny, humble, handsome, loyal, kind, and respectful individuals I’ve ever met. Maybe not someone who can spin me around the dance floor, but someone I could imagine building a beautiful life with.

A few weeks ago, after being single for some months, I reached out via email to see if he wanted to meet to catch up – and he said yes. I was shocked to see that as of a year ago he is no longer with the woman he dated after me. In her blog post, she said the timing was off. Also, every once in awhile, he consults with my parent regarding financial advice (but told my parent to keep this hush, hush). In our email correspondence in planning the meetup, he said he is looking forward to seeing me soon, but wrote nothing that makes me think he has other hopes. My question is, how do I approach the meetup? Do I just have to leave it up to the universe? How much of my feelings should I share with him? I certainly don’t want to scare him away or make the meetup all about me.

My heart feels so full when I think about him. It’s hard to temper my hopes when I feel such deep affection and love for this person, and the timing feels so right. I know there’s a good chance this won’t go anywhere romantically, but I so wish it would.

– Finally Meeting the One Who Got Away