Dear Prudence,
I’m divorced and in my early 30s. I’ve been dating a wonderful woman for a year, but a few days ago came across my college sweetheart’s social media profile. We parted amicably and haven’t spoken in years, but when I saw her picture, I experienced a deep swell of regret and nostalgia. I wondered how my life would have been different if we’d stayed together: I wouldn’t have gotten married and divorced, perhaps avoiding a lot of heartache, plus I’d be living a pretty different life. My ex went straight to graduate school, whereas I was able to travel and work in a number of different cities, and now feel like I’m trying to “catch up” to my peers who stayed in one place and are more professionally settled.
To be honest, I feel a bit envious of my ex and her well-paying job and kind of kick myself for not doing what she did. I also find myself (quite unfairly) comparing my college girlfriend to my current one. I’m having strange urges to contact her, but I feel it would be inappropriate, or maybe just make it harder for me to move on. This is not the first time I’ve had a sudden twinge of regret and nostalgia for other women I’ve dated in the past. My intuition is that this is a random desire from the unconscious coming to the front and I don’t plan on acting on it. But what, if any, reasons would make it sensible to do so? And why do you think these thoughts pop up? I’m sure I’m not the only one.
—Flashback