I recently reconnected with someone I dated back in high school. She was actually the first person I ever fell in love with, and we had a pretty good relationship overall, until youthful arrogance got in the way, and I broke it off. I can’t even really remember the details of why we broke up, but I’m pretty sure she never really did anything wrong, I just wanted a change at the time, and thought I was too cool for her or something.

Fast forward to today and we have started talking again on facebook. She has kids and recently divorced. I’m also divorced but no kids. I never really intended on asking her out, as I hadn’t really consider it a possibility after so long and had thought I was over her a long time ago, but after talking over the last few days, we kind of clicked again, she gives me her number and says she’d love to get coffee or a drink. Now I could be reading too much into it, but considering we’ve already caught up pretty well over messenger, I’m assuming she is interested in giving it another go. We’ve both definitely changed a lot since high school, but given our current situations, it seems like it’s worth a shot overall.

So I’m just wondering if anyone else has reconnected with a high school sweetheart, or knows someone who has, and if so, how it turned out. Is this something that could actually work?

4 comments
  1. Actually reconnected with a high school crush recently.. during my divorce, but only as friends rather than anything romantic (we were always great at helping the other person make hard decisions).

    What I realised was how much I missed having her around because she’s an amazing person. She’s smart, pretty, humorous, sassy, etc. the list goes on.

    However, what I also realised (that maybe she realised many years ago before I did) is that our goals and values are actually a lot further apart than I realised. So while she’s an amazing person, we’d probably both say neither of us fits the other person’s narrative of how we see our lives panning out.

    A lot changes in ~15 years. So make sure you’re dating her for who she is now, not who you remember her to be.

  2. >after talking over the last few days, we kind of clicked again, she gives me her number and says she’d love to get coffee or a drink. Now I could be reading too much into it, but considering we’ve already caught up pretty well over messenger, I’m assuming she is interested in giving it another go.

    Uh…no. That’s a leap you’ve made. Don’t make that assumption. She offered to meet up for coffee, not getting back together.

    >So I’m just wondering if anyone else has reconnected with a high school sweetheart, or knows someone who has, and if so, how it turned out. Is this something that could actually work?

    I personally would never a million years get back together with my high school sweetheart, but these stories being successful isn’t unheard of.

  3. My mom did actually. Though it was like 10 ish years after my parents divorced and not very long after his wife passed away. Supposedly it’s going well but I have my reservations as this guy seems way too ready to just get married and my mom is insane. They have been together for a couple years now though lol

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