High school love: too late to try again?

Tuesday | January 13, 2026

Love Letters Dating

High school love: too late to try again?

Relationships can be confusing. What’s on your mind about your own connections? Send an anonymous question through the form – or email [email protected].

Hey Meredith,

So I fell in love with this guy my freshman year of high school. I couldn’t stop thinking about him, I was a complete mess whenever I spoke to him, and I somehow was simultaneously cracking all the jokes in the world to get this man to chuckle. It was a lot. I was a lot.

Apparently that didn’t scare him off, and when I confessed my feelings to him six months into the year, he said liked me back. I felt like I was in one of those period romance novels. It wasn’t long before we were confessing our love to each other in long letters, and he was getting me flowers every week. It was amazing.

The issue: my parents thought I wasn’t going to date until 26. I was not 26. One thing led to another and my mom made the dreaded ultimatum: either him or her. My grades were also taking a hit, so I just hit the breaks. I broke up with him after two weeks of barely dating each other.

Both of us got hit pretty hard. He got detention, and I got to crying. I don’t think either of us really got over the breakup phase until a year and a half later. We avoided each other in hallways, avoided eye contact, avoided everything. We still haven’t talked for more than a minute to this date.

I tried liking different guys, implementing the mantra that the best way to get over someone is to find someone else. It didn’t work. I still look at him and think about what it’d be like if I didn’t ruin the beautiful thing I had, and what it would be like to be held the way I was held when I was with him. To be loved and seen by someone the way he saw me. To know someone in my life that undeniably loved an un-curated me.

After I broke up with him, my mom said we could revisit dating when I was an adult. It’s my senior year, I finally turned 18, and in six months we won’t be going to any of the same places anytime soon. Should I pursue him? If so, how?

– Never Got Over It

“It was a lot. I was a lot.” “…when I confessed to him six months into the year, he said liked me back.”

You are a bold person! Be bold again. Tell this young man that you’d love to spend time together. Say you’re at a different place in your life, and that you’d like to get to know him in 2026. Ask him to dinner, or maybe a walk around a park with some hot chocolate. (I have no idea what teens do these days.)

You’ll notice I didn’t say, “Profess your love! Speak like a Jane Austen character! Hold him like you cherish him!” That’s because after a year and a half, you’ve changed, had new experiences, developed beliefs about the world, and made plans for the future.

You speak of your time together as peak romance, but it was, as Taylor Swift would say, a fortnight. A blip, albeit a formative and epic one.

Maybe too epic. You don’t want a relationship to be so engaging that your grades slip.

Almost two years later, an outing with him might feel awkward, slow, or even uninteresting. That would be fine. If you start with a simple walk or coffee, the stakes stay low.

– Meredith

Readers? Is it worth pursuing this love even though there’s six months left before big changes? I think so, but I still call my high school boyfriend every year.

Relationships can be confusing. What’s on your mind about your own connections? Send an anonymous question through the form – or email [email protected].

Breakups 🖤 Dating Getting back together High School 🖤

Featured Comment

Sure, ask him out. But you weren’t in love after 2 weeks of dating, you were infatuated. It’s great to enjoy those first weeks or months with someone you really like, but if you expect adult relationships to be 24/7 over the top romance, flowers, and love letters, you are never going to be happy in a real human relationship. You’re young, but just make sure you’re learning this over time with experience and not comparing everyone to the one that got away when you were 14.

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