I want to contact my high school sweetheart

Hi Meredith,

I am a middle-aged man. I have been happily married to a wonderful woman for more than 35 years. We married fairly young, but that was the best decision of my life. My wife has been with me every step of the way. She has enabled me to achieve more in my life than I ever thought I would, and I could not have done it without her. She is my partner and best friend, and I measure my happiness by how much time I get to spend with her. We have two beautiful, successful adult daughters.

So here's the thing: Long ago and far away, I had a high school sweetheart (l will call her "Lisa"). We had an on-and-off relationship for about a year. Things seemed to be falling into place, but Lisa ended it abruptly. I was heartbroken, but I guess most teenage flings end that way. I have not seen Lisa or heard from her in more than 40 years. Despite having a very happy marriage, I have found myself thinking back on my time with Lisa and wondering where she is and how she is doing. To be honest, I think about her a lot. If I had one wish in life, it would be to have some time to speak with Lisa and get caught up on old times and hear her life story.

All this time, I have had no way to contact Lisa. Like many in our generation, she does not do social media. I reached out to her old high school friends, but no one has stayed in touch with her. I go to high school reunions, but she does not go. For many years I have Googled her name just to see what might happen. (Everybody does that, right? Please tell me everybody does that.) To date, nothing - until today. Her workplace recently posted her picture and contact information on its web site, and I found it. My prayer has been answered. So what do I do now? Should I reach out to her, say hi, and see if she would like to talk? Or after all that time, would she be creeped out and think I was stalking her? If I do reach out, should the first contact be e-mail or telephone? I'm thinking e-mail, because if she does not want to hear from me, she can just delete the e-mail without an awkward phone conversation. Any advice would be welcome.

- Boyfriend from the past


If you're going to reach out to Lisa, do so by email. But before you do, please consider your expectations and how you'll communicate them.

I hear a lot of stories about people reaching out to past loves, and in many cases it's because someone has become single again. But that's not what's happening here. You're happily married, so this is a curiosity/nostalgia thing. You'll want to be so clear about that in the first email. There should be no ambiguity about your intentions.

I remember getting a random email from an ex years ago. We hadn't spoken since we were in our early 20s. We went back and forth like six times – long emails – before he mentioned he was married. I was like, "Huh." Even though your history with this woman sounds pretty ancient, she might make assumptions about what you want.

And that's why I have to ask whether you understand your motives here. You've found her through Google, so you know where she works and how she looks. That probably sated some of your curiosity, right? You should think about whether the goal is to pursue a new pen pal,  to trade just one or two emails before disappearing again, or to bring Lisa into your life.

It's very normal to wonder and even fantasize about an ex, but you don't have to do anything about it.

– Meredith

Readers? Email? Call? Nothing?