The One That Got Away: Get Him Back or Let Him Go?

Notes from the podcast:

Navigating the “What Ifs” of Modern Dating: A Strategic Approach

In the whirlwind realm of modern dating, with its endless apps, messages, and meet-ups, managing multiple connections can feel like juggling with too many balls in the air. It’s all too easy for something—or someone—to slip through the cracks. Maybe there’s that person you never got back to on a dating app or someone you decided wasn’t for you a little too hastily. Perhaps there were a few great dates that mysteriously fizzled out or a super nice guy who disappeared from the radar.

The Lingering Question: What Are You Missing Out On?

These missed connections and fleeting interactions often leave us haunted by the tormenting question, “What if?” This question can dangle the possibility of missed problems or a fantastic relationship that just never was. Occasionally, you might be offered a second chance, but the dilemma remains: should you take it?

The Fantasy of Missed Connections

Understanding that the relationships and connections we miss out on become a projection screen for our fantasies is crucial. They morph into anything our hearts and minds desire, often leading us down paths of misery or FOMO as we fill in the blanks with narratives that serve our fears or wishes. The truth is, we might never know what we missed out on—and recognizing this can be a liberating realization.

Dealing with Comeback Stories: A Dual Perspective

1. The Instant Chemistry Cliffhanger

These are the encounters characterized by immediate attraction and sparks flying, only for communication to suddenly dwindle and vanish, leaving you with no closure. The hard truth? The lack of follow-up is, in itself, closure. Actions—or in this case, the absence thereof—reveal priorities. The strategy here is to let go, from hoping for a comeback to being the chooser, not the chaser. Early sparks, while thrilling, are rarely indicators of long-term compatibility. Beware the boomerang boyfriend, who only reappears once you’ve moved on, hoping you’ve lowered your standards.

2. The Sparkless Good Guy

Then there’s the guy who ticks all the boxes—good conversation, solid character, seemingly stable—but lacks that initial spark. Maybe he seemed a bit dull, too self-focused, or nervous. It’s easy to dismiss these connections in search of fireworks, but the slow burns often promise lasting warmth. Giving these individuals a second chance (but not a third) can sometimes reveal hidden depths and lead to a fulfilling relationship.

Wrapping Up: Embracing Strategy Over Regret

Regret is a challenging emotion fueled by the distorted fictions of “what could have been.” While dwelling on missed opportunities is tempting, it’s more productive to recognize that things often don’t work out for good reasons. However, there are genuine opportunities for connection among the noise—if you know where to look and are willing to give things another shot, albeit with a bit of strategy in your step.