fb-pixel Skip to main content

I compare everyone to my high school sweetheart

‘It has been almost 30 years and I still think about her every day’

Love Letters
Love Letters

Q. I am still not over my high school sweetheart. It has been almost 30 years and I still think about her every day. I no longer feel pain but I do miss her and will always love her. I was married, now divorced, and in all of my relationships, none compared to what I had with my high school sweetheart. Unfortunately, she is happily married with children. We recently “caught up” by talking late into the morning over text. It was as if we never stopped talking. We joked around, shared memories, laughed, etc.

After that interaction, she has grown distant. She is uncomfortable talking to me because she does not want her husband to find out. She has no intention of leaving her husband. But I continue to think about her on a daily basis. This may or may not end up affecting my future relationships, if I have any.


Thanks for listening!


A. We say this a lot in the Love Letters column, but sometimes when we’re longing for a person from our past, we’re thinking about the when and maybe less about the who. I don’t know what high school was like for you, but this woman’s role in your world back then was clearly meaningful. Formative. Fun. Important. But you did break up for some reason. You were not able to grow together — or one of you, at the very least, wanted other experiences.

You have no idea how she’d fit into your life now. Sure, you’ve fantasized about what it might be like, but that’s fiction. You don’t know whether she gets annoyed with shared household tasks, what kind of partner she’d be during a quarantine, or how attracted you’d be to each other as grown-ups. In fact, all you know is that you’re making her uncomfortable. Doesn’t sound like a match to me. Your goal should be finding someone for now. Someone who works for you in 2021.


Why would you compare prospective partners to a person who made you happy as a teenager? Honestly, it sounds like an easy way to dismiss anyone who crosses your path. It’s like me comparing men to my poster of Christian Slater from 1992 ... which was on my ceiling until 1995. The poster was from the early 1990s comedy “Kuffs,” which was not very good! Yes, the film still exists in the world, and maybe I could get through watching it for kicks on some random night, but I think I can find something — and someone — better to spend my time with now.

(No offense, Mr. Slater. I do still love your other work.)



It’s normal after a divorce to take inventory and do a life review about all the things you’ve learned about relationships, what worked, what didn’t, but you’re not supposed to stay there.


You have to leave her alone. You also have to deal with whatever it is in your life that makes you idealize this person and this time from so long ago. She is happily married with children. Nothing good can come of this.


You are infatuated with a fantasy. Who she was in high school is not going to be the same person she is now. Good for her for setting some boundaries — don’t be surprised if the next step is her blocking you/cutting off contact if you keep pushing. I’m throwing the therapy card — it’s normal to think about the past, but you’ve been obsessing over this woman for 30 years!



She had fun catching up with you, and now you are trying to push it into being more than that. She is telling you to let it go. Listen to her about moving on, and be grateful she gave you the time to reminisce.


You can have nice memories of a relationship decades ago, but life moves on. You can’t stay stuck in the past. No one should. You need to create your own life and find things that make you happy in the present. No, you won’t magically fall in love instantly and replace all your feelings; and you shouldn’t because every person and every relationship is different. Please get counseling to help you put your high school past in its place and develop coping skills to move on.


Send your own relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.