Sitting in Chicago on a weekend nearing the holidays makes me think back to another weekend seven years ago. I was away from my children during the holiday season after my divorce.
I had lined up my first Tinder date with a gentleman I’d messaged only once. A rookie in the online dating world, wildly naïve and optimistic, I contacted him after reading his profile, thinking he seemed like a suitable first date. He was in Chicago, and I suggested we meet while I was there anyway.
Before my date, I took a stroll around the city. I saw families with kids on their dads’ shoulders, looking at lights and celebrating the holiday season. My heart sank. The reality I tried to compartmentalize and escape from by coming to Chicago slipped back into my consciousness. Confronted with the realization of the lifetime in front of me—missing the holidays with my girls—a fog of disappointment drifted over me.
I realized I didn’t want to go on that Tinder date. I needed to process my grief and postpone. As this recognition moved into awareness, I slid into a velvety bank of chairs in the hotel lobby, ready to message Tim and tell him I wouldn’t make it.
But first, I heard a voice next to me. I looked over to see a priest greeting me. Now, I have a long history of run-ins with the collared and ordained, so I wasn’t surprised when he struck up a conversation.
“Did you know,” he said, “that the more options we have, the more unhappy we are?”
Turns out he was a sociologist as well. “The more options we have before us,” he continued, “the more we compare, analyze, and feel a sense of missing out on what a better option might be.”
If you’re skeptical, look into the research on the Paradox of Choice. It turns out people generally fall into one of two categories: maximizers or satisfiers, though new categories in dating have emerged. Maximizers want to explore all the options and find the best one, whether it’s a product or a partner. They set high standards and often achieve excellent outcomes but are prone to dissatisfaction, always wondering if something better is out there. Satisfiers, on the other hand, focus on fewer criteria, trust their intuition, and tend to feel happier and more content with their choices.
How timely, I thought. The universe was serving me up some much-needed insight as I embarked on this new chapter. I messaged Tim to let him know I was canceling—to talk with a Jesuit priest about choice. He still teases me about this, five years later. We ended up meeting for coffee the next day, though we didn’t match romantically, and we remain friends to this day.
So, what about you? Where do you land? Are you a maximizer, a satisfier, or someone who wobbles between the two? Do you look at dating profiles and see potential partners, or do you see missed opportunities? More importantly, when was the last time you paused to consider what you truly want and need in a connection—not just what looks good on paper?
Dating isn’t about ticking boxes or avoiding imperfections—it’s about showing up as your whole self and allowing others the space to do the same. It’s about courage: the courage to take a chance, the courage to walk away, and sometimes, the courage to stay. Every stumble, every lesson, and every connection has the potential to move us closer to the love we deserve.
You’re not just navigating a sea of profiles; you’re navigating your story. And even if the next chapter doesn’t lead to forever, it could bring you something equally transformative—clarity, healing, or the discovery of just how resilient your heart truly is.
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