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I Went Down The Rabbit Hole Of Looking Up Old Boyfriends On Social Media

Here's the surprising thing that happened as a result.

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Susanna Gentili
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I’m 57 and have been in a happy, monogamous relationship for 17 years. So why did I go down the rabbit hole of finding old boyfriends on Facebook recently? Boredom. Curiosity. Fun. 

I don’t want to reconnect with any of these men in person or rekindle a relationship. To be very honest, it was merely a game to pass time. 

Here’s how it went down.

First I contacted my very first boyfriend, who is now married. He was the best first boyfriend a girl could ask for. I broke up with him to go out with a “bad boy.” While breaking up with him and exploring other relationships was a normal thing for a 17-year-old girl to do, to this day he is the proverbial one who got away. 

Our encounter on Facebook was wonderful. I expressed my sympathies on the loss of his father as an entrée to an exchange of words, and what resulted was a cordial reminiscing and welcome updates to our lives. There was no flirting or hints of wanting more on either side. It was simply a positive and innocent exchange. I doubt we’ll stay in touch on a regular basis, but it would be nice to hear from him now and again. I do feel fortunate that our exchange was kind and poignant, as I wasn’t very nice in the way I broke up with him.

Next up was the aforementioned bad boy. Married, divorced and now single. I admit that I would pursue more than friendly contact if I weren’t committed to a wonderful man and were 50 pounds lighter. This boyfriend was the one I was head over heels in love with and to whom I was very physically attracted. The unfortunate excuse for my contact was again the loss of a parent — his mother. I expressed my condolences, and one or two back and forth replies were all that transpired. I doubt we will keep in touch — except for the occasional update on something monumental in our lives or expressions of sympathy. Although the added complication of neither of us being married (and gosh, he was so cute) does make this situation a little different than the first.

Finally, I contacted my middle school crush. It was 1976 and I thought Andy was the coolest boy ever. Our romance consisted of just a few awkward phone calls and a mutual love of the TV show Get Smart. Alas, our friendship never blossomed into more, but it was really fun to connect with him 45 years later!

I never heard back from one man (my high school crush), and I’m already in friendly and frequent contact with two other ex-love interests. What did I learn from my experimentation on social media? It is possible to be friends with an old flame. If you’re not in a content and secure relationship, the potential for trouble does exist. My advice is to be aware of your intent and clear with those intentions. The end result could be a warm resurgence of memories and even some closure to unfinished business.