Rekindling a school-days sweetheart

by Dating Goddess on September 9, 2010

Have you ever daydreamed about an old sweetheart from decades ago? What’s he up to now? Is he single? What’s he look like? If you connected, would the spark still be there?

My cousin reconnected with his high school love during their 40th reunion. They had remained close after they broke up in high school, even being in the wedding party for each other’s first marriages! They had lost touch and hit it off again instantly at the reunion. Both were single again. She said she’d love to keep in touch, so he called the next week. The 10-hour drive didn’t keep them apart. He began to woo her and a year later, they were married.

Years ago, when I was married, I got a call from a man I lived with for a year right out of college. He sounded just as stoned as he generally was when we were together, but he was 40 when he called, divorced and with a child. I had no interest in seeing him again.

I also heard from a college sweetheart about a decade ago. He is 8 years older than me, but when he sent his picture, I didn’t recognize him. He looked so old! Solid gray hair and beard, significant weight gain. I wondered what he’d think of how his 21-year-old love had turned out.

A man I had a crush on in high school recently looked at my profile on He’s still good looking and has a successful business. I waited a few days and since he didn’t connect, I sent him a friendly, “let’s catch up” email. He responded, but no overture to get together. He’s looked at my profile several times since, but I won’t be initiating contact again. I remember him as a good guy with an easy smile. I am curious to see if he has the same solid character he did as a teenager.

Have you considered rekindling a relationship with a high school or college sweetie? Have you ever actually met with someone you went with then? If so, what happened?


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