The return of the one that got away

Hi Meredith,

Tim and I dated for a year in college (6 years ago), half of which was long-distance. He was, and is, an amazing person. Smart, funny, caring, and carries some kind of karmic energy that just seems to click with me. The distance part worked fine for a while, but once he graduated and got a job and I was still in college, it was difficult to keep the relationship intact. He ended it, I didn't beg, but made my opinion clear that I wanted to try to make it work. It was the worst heartbreak I've ever had (I was only 20!) I've dated several people over the years, but no one that comes close to how I felt (and still feel) about Tim.

Last week, he texted me to say he was in Boston (he lives out of state) and asked if I'd like to meet up. I haven't seen him in 5 years, and have only been in sporadic contact via email and texts a few times over the years, so this invitation came as a surprise, but I was excited to hear from him. We sat in a Starbucks for 2.5 hours talking until I realized I would be late for work and had to leave. I would have stayed all night! He told me he had gone through a rough time about a year ago, including receiving a diagnosis of depression, for which he is now receiving treatment. He said that he really wants to keep in touch and made it a point to say that he will call. He asked about my love life and I was honest, but didn't ask about his. The time with him was amazing and fun...and it's been distracting me ever since.

I know a part of me will always be in love with him, but now that I've seen him, I'm curious if things could work between us. Distance is still an issue, although I am not against moving. My friends know he was the one that got away and are saying things like "you never know" and encouraging me to act on my feelings. He seemed happy, but depression can be delicate and I don't want to throw any wrenches his way if he's still trying to stabilize. I don't want to chase and I'm afraid of being rejected again, and risk losing him. I think I would much rather have him as a friend than nothing at all, but is that possible with feelings like this? Is it silly for me to be thinking this way after one meeting? Do I tell him how I feel? If so, how soon? If not, what do I do about the friendship part?

Any words of comfort?

– Nostalgia or true love?, Boston

It's not silly to feel this way after one meeting. You loved Tim. You've been thinking about him for years. And then, like magic, he's sitting across from you at your local Starbucks, behaving like a self-aware grownup who's interested in your life.

My advice is to contact him (not a text; email or phone is fine) and tell him that it was great to see him but that it was also rather confusing. Admit that you felt some sparks. Ask him if he felt the same way. Honestly, it's a low-pressure question. You're just asking if the meetup gave him a few butterflies. If he says that it did, you can ask more questions. If he says he was butterfly-free, you'll be able to make some informed choices about how to reciprocate contact with him in the future.

Just don't feel silly or stupid. If my one that got away showed up and took me out for coffee and looked interested in me for 2.5 hours, I'd probably go home and daydream for 2.5 hours about our next first kiss. Your reaction is understandable.

It might be nostalgia, but that doesn't mean it can't become something real. Just find out sooner than later so that you don't stew too much about the what-ifs.

Readers? Is this all in her head or is this a real possibility? Is the depression relevant? Should it stop her from contacting him about a romantic relationship? Is this nostalgia? Thoughts on Tim's motivation for getting together? Help.

– Meredith