Love Letters

I’m happily married, but I tracked down my first love. Now what?

She rejected me decades ago, and for some reason I really want to hear how her life turned out.

Catch Season 2 of the Love Letters podcast: How do you meet someone? Subscribe here: Apple Podcasts | Spotify | Other

Q. Hi Meredith, I am a middle-aged man and happily married for more than 35 years. My wife is my best friend, and I measure my happiness by how much time I get to spend with her. We have two beautiful adult daughters.

But long ago and far away, I had a high school sweetheart, “Lisa.” When Lisa ended things abruptly, I was heartbroken. I have not seen or heard from her in 40-plus years. Despite my very happy marriage, I have found myself thinking back on my time with Lisa. If I had one wish in life, it would be to speak with her and hear her life story.

For many years I have Googled her name (everybody does that, right?), but there was nothing online — until today. Her workplace posted her picture and contact information on its website. My prayer has been answered.


Should I reach out to her and see if she would like to talk? Or would she think I was stalking her? If I do reach out, should the first contact be by e-mail or telephone?

— Boyfriend from the past

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A. If you reach out to Lisa, do it by e-mail. 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 very clear about that in the first e-mail so that there’s no ambiguity when it comes to your intentions.

I remember getting a random e-mail from an ex years ago. We went back and forth like six times — long e-mails — before he mentioned he was married. I was like, “Huh.” It felt dishonest. 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 truly understand your motives here. You’ve finally found her online, 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 e-mails before disappearing again, or to bring Lisa into your life.


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

— Meredith


I recently had an old flame contact me, and I still haven’t responded because it’s really not a door I wanted opened. Ask yourself what you really hope to accomplish by this. ENJOYEVERYSANDWICH

I’m also sometimes curious about old boyfriends. I look for them on Facebook or maybe Google them. I don’t even bother “friending.” What do I have to talk to them about? ASH

Here’s a way to figure out how innocent your intentions are: Did you tell your wife about how you just want to “catch up” with Lisa? MANBRAD2581

She has not contacted you, attended reunions, or built a network on social media. Lisa is not going to be overjoyed to hear from you. Please leave this woman alone. CAKESNIFFER

Get Season 2 of Meredith Goldstein’s Love Letters podcast now at or wherever you listen. Column and comments are edited and reprinted from Send letters to