The Philosophy That Significantly Improved My Dating Life

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e met at a wine bar, my first Hinge match and I, a week after I moved to the city. The date went well — really well. You know that fluttery heart feeling? It flitted through my whole body. Future dates took shape in my mind: afternoons at the Guggenheim, picnics in the park with a bottle of white. Maybe we’d fall for each other — we had so much in common — but we’d take our time. Neither of us was looking to jump into something.

Within a few weeks, things had taken a turn. There were texts that went unanswered for three days, late-Friday-night follow-ups littered with apologies. Was he not interested or playing hard to get? Indifferent or unsure? Neither seemed appealing, but I chalked it up to what everyone says: Dating is hard.

I navigated this undefined territory for six months, probably four longer than I should have. By the time the pseudo-relationship came to a fiery end involving arguing and tears on my apartment stoop, the fluttery feeling had long gone, replaced by the sneaking suspicion that dating is, in fact, pure bullshit.

My friends were by my side for the whole saga, offering condolences in the form of their own horror stories. One experienced bad date after bad date, regularly annoyed that she had wasted her time yet again. One took me through a novel of texts nearly every day, actively navigating her own role in them: How long should she wait to reply? Happy hour after work or Saturday night drinks? We talked through everything exhaustively, all of us playing the role of wise expert to one another, but never getting it quite right ourselves.

It wasn’t until I met a woman named Meghan Holzhauer (whom I interviewed for a story about couples who work together) that I realized it didn’t have to be this way. Meghan told me about “intentional” or “deeper dating” — a philosophy she learned from her life coach that changed how she thought about dating. I’d never heard of it, but upon further exploration, I learned the concept has been circulating around small corners of the internet and in dating books for a while, albeit mostly ones aimed at the midlife crowd. (A quick Google search of “intentional dating” also brings up a lot of religion-focused articles, which is different from the concept I’m referring to here.)

The deeper dating philosophy doesn’t require you to be serious about finding “the one.” In fact, it encourages you to take the future out of the equation entirely, treating each date as a full relationship in and of itself. This means that rather than reserving true intimacy for later down the line, you make it a feature of every encounter — by first acknowledging the parts of yourself that you’re usually hesitant to reveal, and then unabashedly putting them on the table with the understanding that humans connect to other human feelings. Achieving this connection requires a willingness to be vulnerable, first and foremost, but also a commitment to enjoying or learning from the few hours you have with someone, honoring their most human traits, too — even if the romantic attraction or “spark” isn’t there. It’s about dating purely to find connection with others at any level, rather than dating specifically to find a partner.

Upon first reading, I was struck by the flexibility of the approach. Particularly with the way it reconfigures my “bad dates” into experiences in which I learn something about someone, or at least learn something about myself. Like the date who asked me to play Bananagrams — our personalities might not have clicked enough to warrant more dates, but he reminded me that a little nerdiness is essential to me in a relationship. Or take my most recent date, who showed me an 11-minute photo montage video, set to music, of his recently-deceased dog. I found that decision downright fascinating. Whereas before I’d have considered these dates a waste of time, now I see them as more than worthy of it — simply because I came away from them with a more expansive understanding of people and myself.

I’ve gone on over a month’s worth of dates since I committed to exploring these ideas, and I’m surprised to say that dating has become something I’m excited about. It’s given me the push to meet people who aren’t usually “my type” — which have turned into some of the best dates I’ve ever had. For me, the key to making the philosophy work is seeing all forms of connections as equally compelling. It was a bit of an adjustment at first, but I’ve found that when the dates do go well romantically, they’re much better for it, because they’re infused with openness and vulnerability. As Brené Brown wisely said, “In order for connection to happen, we have to allow ourselves to be seen, really seen.” (Please watch her TED Talk if you haven’t yet.)

Individually, the traits that make up the deeper dating movement seem like clichés you’d read on an inspirational mug: Be yourself. Live in the moment. Accept others. But when combined, the platitudes have informed an entirely new approach to dating for me — one that eliminates a lot of the questions, worries, and “how to play it cool” Google searches, by taking things one date at a time.

Does this philosophy resonate with you like it does with me? Have you gone on any “deep dates”? How did they go?

Illustrations by Meredith Jensen.

Jackie Homan

Jackie Homan

Jackie Homan is a journalist, writer, and proud owner of an indoor s’mores maker for the rainy days.

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