Can I reach out to her?

I'd like to run some updates next week. If you're a letter writer and can update us on your situation, please email me (meregoldstein at gmail dot com) with the word "UPDATE" in the subject line. Tell us what's up -- and make sure you send the email from the account you used to send the original letter so I know it's really you.

I'm a man in his mid to late 20s who has made some mistakes in his life. In my early 20s, I treated women like they were conquests. I realized what I was doing when I was 23, felt guilt, and buried myself in a not-so-great three-year relationship (I was treated like a doormat until I walked away). I have spent some serious time thinking about one girl in particular who I met before I was in that relationship.

I met this particular woman when we were freshmen in college and I instantly fell in love with her. The problem was that I was a "grass is always greener" guy back then. For five years she and I dated on and off until I officially ended it. She saw what was good in me. She always saw past my bravado and would keep me in check. We haven't spoken in 3 years and I want to reach out to her. Not because I instantly think we should get back together but because I sincerely want to apologize. I have lived with this guilt for years now because I know in my heart that I should have stuck with her. I also know that I screwed her up emotionally. I believe people can change and I know that I have.

Do you think it would be a bad idea for me to reach out an apologize after three years of no contact?

Eventually we will cross paths because we have mutual friends who have weddings coming up. I know with my luck we will be seated at the same table because our friends have sick senses of humors and always loved us together. What should I do?

– Time Changes, CT

I'd wait until you see her at the weddings, TC. It's been three years. You don't know her anymore. You're romanticizing the relationship and thinking of her as the soul mate you left behind. In person, you might want to give her a quick apology and walk away.

If you want to give her a real, extended apology after seeing her, go for it, but keep your expectations low.

A disclosure: I've been on the other end of this kind of apology (Draco Malfoy). Getting it made me angry -- because it put me in the position of having to focus on someone who had already sucked up a lot of my time. I remember complaining to friends that the ex’s apology note was symbolic of so much -- that even after years of no contact, he was still reaching out to say, "Me! Me!"

But ...

I wouldn't undo the fact that he sent it.

The thing is, it was nice to know that he felt like an idiot, and it was therapeutic to read (via email – that's the best way to reach out) that he understood the importance of the relationship.

My advice is to do what feels right in your gut after you see her. And if you send the note, don't focus too much on yourself. "I feel ... I need ... I did ..." ... those kind of phrases are going to make her roll her eyes. Keep it to an apology and some honesty. As in, "I don't know if writing this note was a good idea ... it might be selfish. That said, I want you to walk around knowing that I've always understood your awesomeness." If she writes back, fine, but make it clear that she doesn't have to.

Get yourself to those weddings and then do what feels right.

Readers? Should he reach out? Are his intentions pure? Would you want to hear from him if you were the ex? Should he wait until he sees her at these weddings? Help.

– Meredith