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Advice

My high school sweetheart is back and I’m falling for him all over again. But there are some red flags.

  • Author: Wayne and Wanda
  • Updated: June 22
  • Published June 22

Dear Wayne and Wanda,

I was recently contacted online by my first love. We were high school sweethearts who broke up when I went away to college. He ended up dating and marrying one of my best friends. When they got together, my heart broke all over again, and it ruined my relationship with my friend. I hadn’t seen or spoken to either of them in years.

So imagine my surprise when I had a message from him a couple of weeks ago. He said they’re getting divorced. He said he’s never stopped thinking about me.

It’s not an understatement to say I had literally dreamed of this happening. Part of me never got over him and always imagined us somehow reuniting. Since that first message, we exchanged a flurry of emails and then moved on to phone calls and video chatting. Yesterday he told me he has fallen for me all over again and wants to be with me.

He is in Seattle and I’m open to moving. At the very least, I want to go visit him and see where we stand. My friends think I’m being crazy and are telling me not to pursue this. My heart says otherwise. Any advice?

Wanda says:

Whoa, whoa, whoa. Open to moving? He’s fallen for you? It’s only been a few weeks? His divorce isn’t final yet? Three words: Pump the brakes.

Look, I get it. Reconnecting with a former flame is exhilarating. There’s lust in spades, with years of fantasies to fuel the fire. And let’s be honest, after he pretty much rejected you way back when to marry your BFF, it must feel awfully sweet and redemptive to know he DM’d you the second he was free. You could even tell yourself that it’s like it was always meant to be — you and him, sitting in a tree, k-i-s-s-i-n-g, happily ever after and all that jazz.

But here’s what’s really happening: You guys broke up a long time ago, many years have passed, you’ve both no doubt changed a ton, and now you have very different lives and even live in different states. Meanwhile, he’s going through a divorce and is no doubt spinning from that. It makes sense he’d revert back to something familiar — that being you. You know another word for revert? Rebound. And the thing about rebounds is, they generally don’t last.

Enjoy the flirtation if you must, but slow down — and open your eyes. Or this guy will break your heart all over again.

Wayne says:

Hey, if this is your fairy tale, go for it. Seriously. Your friends are right, of course: This is crazy. And you clearly agree to some extent. But life is crazy and it’s certainly been a wild ride for you both to finally get to a place where you have an opportunity to be together again … and possibly forever. And, well, crazier pairings have happened. And oftentimes, there isn’t a chance to have a second chance. So if this is truly what your heart is telling you to do, if this is truly the man you have dreamed of spending the rest of your life with, push your chips all in and do it.

Go through with this and you’ll never have to question if he was indeed “the one” or if you two were meant to be together. If it crashes and burns, at least you’ll walk away from the wreckage with that clarity. And if it works out, well, you’re living the dream.

Of course, you could listen to your brain and all of the smart people who want the best for you, like your friends. They have all sorts of perfectly logical reasons why you should lose this guy’s number ASAP. They can also continue pointing out all the really big red flashing warning signs on this already bumpy road, but you’re clearly running over all of those signs, through any roadblocks and past any patrol cars. You don’t want to listen to your brain, your friends, two romance expects, or anyone else anyway. So to heck with it — just go for it. Good luck.

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