Ditch Your Dating Wrapped.

As we all know, the holiday season is a time for loved ones, nostalgia, reflection, and mentally stitching together a very loose timeline of everything that’s happened in your life since the last time you saw your long-distance friends in person.

Now, everything I’m about to say should’ve been grossly evident in the way I write, but in case it wasn’t already clear: I love a story. I love a narrative. I love a “keep in mind” or “remember this part” moment. Most importantly, I love an unexpected twist—the kind that gives shape to everything I’m saying while keeping my friends entertained as I explain how I ended up wherever I am at the moment.

So naturally, every year around this time, my tell-all sessions with friends end up sounding like “hobbies and interests wrapped,” “career wrapped,” “friendships wrapped,” and, as the title suggests, a “dating wrapped.”

There’s something deeply satisfying about being able to package a year of your life into digestible highlights, especially when there’s a little drama, a little growth, and a few characters who didn’t make it to the final act.

I mean, what’s a good story without a clean arc? A true beginning, middle, and end?

However, after the most introspective date I’ve ever been on a few days ago and with impending confessionals to friends either in town or waiting on updates, it became clear to me that if I really do want the kind of partner I claim I’m looking for, I can’t keep dating just so I have a good story to tell.

If you’ve spent any amount of time on this website, you’ve probably also noticed that I go on and on about intentionality, being genuine, non-performative, and unabashedly yourself. And I truly believe I live that way in nearly every aspect of my life.

Except dating.

Why?

Because unlike all of those other areas, when you date intentionally, there’s really only one direction things can go. And if you’re honest about wanting a partner who helps you become the best version of yourself, then you have to be deliberate about burning loose ends and letting go of subplots that don’t actually lead anywhere, even if their presence makes the story of your life feel more interesting.

I think I’m reaching an age where I just can’t tolerate the ambiguity anymore. Whether it was attending two weddings this year or being asked by a close friend, “Wait, you’d actually want to get married??” those moments forced me to confront my own desires in a way I couldn’t ignore. They made me realize that I’m not clearly presenting what I want to the world, and if I expect anything to change, there has to be action on my part.

My solution is simple, and it’s inspired by one of the first frameworks you learn in any marketing program.

Shifting from a Dating Wrapped to a Dating SWOT forces me to move past the “Oh my God, girl what happened???” and toward the question that actually matters: why will (or won’t) this work?

For context, a SWOT analysis evaluates Strengths, Weaknesses, Opportunities, and Threats—not based on vibes or first impressions, but on alignment, sustainability, and long-term potential. You don’t do a SWOT to tear something down; you do it to determine whether or not it’s something worth building on.

So instead of recapping, I started analyzing after my date.

What made the night different wasn’t just that we talked for hours. Rather, it was what we talked about. It was never discussions of aspirations in the abstract or the usual “what do you do / where are you from / what are you looking for” loop, but my principles & beliefs, tested in real scenarios. I mean, he even asked me what I valued, full stop. Not what I wanted out of dating, not what I was working toward—what I held close. Empathy and my independence, in case you were wondering my response.

We talked about family dynamics and expectations, not nostalgically, but structurally: roles, priorities, assumptions.

At one point, he asked me who taught me to step aside so a man could open the door. I laughed because it sounded absurd out loud, but then I realized I didn’t have a real answer. No one had ever asked me about that reflex before. He wasn’t challenging me—he was trying to understand the belief system underneath the behavior.

That became the theme of the night: not collecting answers, but tracing them back to their source.

Even conversations about communication weren’t hypothetical. He painted real pictures, for instance, an ex asking for his opinion on an outfit, him being honest, her disregarding it anyway.

Were you offering the perspective or were you attempting and hoping to assert control? What’s the point of asking if you don’t want the truth? What does honesty actually require of both people? What solutions would even make sense?

A perfect case study to beg questions like these.

It was the first time I realized how often men ask questions that sound deep but collapse once you answer them. These didn’t.

He spoke about discomfort—social, cultural, ideological—and how his solution is almost always distance. No disruption. No negotiation. Just removal. He framed it as respect, as not wanting to disturb the balance of a room or impose his beliefs on others, though it was hard to fully believe him.

“I’ve learned how deeply ignorant people are to others, and that it’s a shame,” he said to me.

Only later did I realize what was woven through all of it: his instinct to preserve peace by opting out.

He doesn’t read or watch documentaries. He sits with his own thoughts and waits for interactions to come to him. He knows his own experiences, and a few others that have crossed his path, and uses those as the foundation for his belief system.

I’ve seen this lack of curiosity in other people. It allows distance to stay intact. If you never seek out the unknown or step into discomfort, you get to remain in one place.

I thought to myself about the spaces he won’t enter, the people he won’t sit with, and the conversations he will always choose not to have.

I actually shed a tear or two. He understood my counterarguments and rebuttals, yet remained unmoving, convinced these thoughts were simply wrong to hold.

That’s when the framework fully clicked—not as a checklist, not as a verdict on him as a person, but as an evaluation of alignment. Strengths that genuinely drew me in. Limitations that weren’t flaws, just realities. Compatibility that felt rare. High tensions that, if ignored, would eventually turn into fractures.

For the first time, I wasn’t asking myself, Will this be a good story to tell later? I was asking whether the structure of his life could actually support the partnership I say I want. And that question doesn’t care how charming the night was or how intrigued I felt driving home.

So no, I’m not doing a dating wrapped anymore. I’m learning how to look at people the way I look at strategy: holistically, honestly, and with the understanding that not everything compelling is sustainable.

What this date showed me is that nothing about it failed, and that’s exactly why it mattered. There was chemistry, curiosity, attraction, and genuine intrigue. It just didn’t point toward a future that aligns with the life I’m trying to build. And that’s the uncomfortable truth of dating intentionally: realizing that connection alone isn’t enough.

It’s not about waiting for something to go wrong.

It’s about recognizing when something simply won’t go forward.

And, Adi, sorry I didn’t respond to your text asking me what I meant by “I just went on the most introspective date ever”. I was busy writing this.