Keeping up with Kay

For something that so many people experience, dating is surprisingly hard to talk about honestly. We swap stories with our friends over dinner or during late-night phone calls, but rarely do we stop to think about what those experiences actually teach us. Somewhere along the way, dating becomes its own little social experiment: two people sitting across from each other, trying to figure out if the conversation flows, if the energy feels right, and if the person in front of them might fit into the life they are building. Some dates feel easy and natural, some unmistakenly bad, and some fall into that wonderfully awkward category that only becomes funny in hindsight. Over time, I’ve realized that dating really is a bit of an art form, equal parts chemistry, timing, effort, and intuition. Which made me start to wonder: what actually makes a good date…and how do you know when it is simply not meant to be?

The Good

Good dates have a way of feeling effortless. The conversation flows naturally, you lose track of time, and for a moment it doesn’t even feel like a “date”. It just feels like two people enjoying each other’s company. There’s curiosity, laughter, and that subtle sense that both people are equally invested in being there.

One of the best examples of this for me started in a way I honestly didn’t expect. I met someone organically at a bar; something people always say happens, but I had secretly started to believe was more myth than reality. We instantly hit it off, realized we had a lot in common, and less than twelve hours later we were sitting across from each other at a coffee shop for our first date.

From there, the dates were a little bit of everything: coffee shops, walks through the city, Topgolf, cute boutique lunch spots, nice restaurants. It was almost like we were unintentionally sampling every type of date possible. What made those dates good wasn’t necessarily where we went, but how easy it felt. Conversation came naturally, there was effort on both sides, and we genuinely enjoyed spending time together.

Now sometimes, even the good ones don’t work out. In this particular case, there was one small…lifestyle detail that eventually became difficult to ignore.

He exclusively ate beef and rice. Only beef and rice.

And while I respect commitment to a diet, at some point you realize that certain lifestyle differences might be harder to navigate than expected. To this day, he is affectionately known among my friends as “Beef and Rice Boy”.

Another good date I went on actually came through a friend who set us up. We met at a brewery in the middle of summer, one I had been wanting to try for a while, so it already felt like a win-win situation. The weather was perfect, the Phillies were on, and the conversation flowed easily as we talked about traveling and places we wanted to see. It was one of those dates that just felt comfortable from start to finish. In the end, it didn’t work out simply because of the distance. Sometimes life logistics make things harder than the connection itself. But it was a good reminder that good people are out there, even if the timing or circumstance don’t quite line up.

One of the more unique dates I went on involved axe throwing. When he suggested it, I remember thinking how different it was from the usual dinner or drinks. It was my first time trying it, and I quickly realized that activity-based dates can actually be great for a first meeting. If the conversation slows down, you still have the activity to fall back on, which keeps the energy fun and light. We talked about travel, shared stories, and laughed over our very questionable axe-throwing skills.

That one didn’t turn into anything long-term either, but it was still a genuinely good experince.

And that is something dating has taught me: a date doesn’t have to lead somewhere to be worthwhile. Sometimes a good date is simply two people showing up, enjoying the moment, and realizing that even if it doesn’t turn into something more, it was still time well spent.

The Bad

Bad dates are usually easier to identify than good ones. Sometimes it’s the conversation that feels off. Sometimes it’s the energy. And sometimes, the red flag reveals itself before the date even really begins.

One date required a bit of travel. He lived far away so we agreed to meet somewhere in the middle. He suggested a place I had never heard of before and described it as a restaurant. In hindsight, this is probably where I should have done a little more research.

The moment we walked in, the entire place went silent. And by “entire place”, I mean the bartender and one man who appeared to be several shots deep at approximately six o’clock in the evening. There was no host, no waitress, and no sign of what I would normally associate with a restaurant. We sat down at the bar while I looked around for a menu, wondering what kind of food they served. The menu consisted of drinks…and hot dogs.

Not specialty hot dogs. Not gourmet hot dogs. Just boiled hot dogs, with a selection of toppings you put on yourself like you were at a baseball game. It wasn’t even one of those trendy dive bars where the chaos is part of the charm. It was more like the kind of place that only locals knew about, and even they seemed surprised to see us there.

That was our first and only date.

But sometimes the problem isn’t the location, it is the personality.

Recently I went on a date with a lawyer, and I’ve learned that dating lawyers can go one of two ways. They can be ambitious, intelligent, and passionate about what they do while still being able to separate their career from their personality. Or… the career becomes the entire personality.

In this case, it was the latter.

I arrived a few minutes late after getting off at the wrong train stop, four minutes late to be exact. His first comment was that he hoped I liked my water warm.

We ordered drinks and when they arrived, he raised his glass for a toast. I assumed it was a simple Friday-night cheers. Instead, he very seriously suggested we toast to defending the Pennsylvania Commonwealth. And suddenly I found myself wondering if it was too early to order a second glass of wine.

Later in the conversation I mentioned that I enjoy traveling alone sometimes. It is something I’ve done and genuinely liked: the freedom, the independence, the chance to explore somewhere new at your own pace. He responded by saying that he personally values sentiment too much to travel alone. For him, experiences were meant to be shared. It wasn’t said directly, but the implication hung in the air for a moment—as if choosing to travel solo meant I must not appreciate those experiences in the same way.

It was one of those moments where you realize the person across from you isn’t really curious about your perspective, they are more interested in explaining it to you.

Dating has taught me that confidence is attractive, but humility is essential. Someone who knows who they are without needing to constantly prove it tends to be far more interesting than someone who reminds you of it all night.

The Awkward

Then there are the awkward dates.

Not bad enough to qualify as disasters, but just slightly off rhythm. The kind of dates where everything seems perfectly normal at first, but every now and then a moment pops up that makes you pause and think, hmmm.

One person I went on a few dates with was genuinely very sweet – polite, thoughtful, and a little awkward in a way that was honestly kind of endearing. We went to a restaurant one night, and for the most part the conversation flowed pretty naturally. But every once in a while, there would be these moments where neither of us quite knew how to transition to a new topic.

At one point, I casually mentioned sharks, because cage diving with them is a bucket list item of mine. Unfortunately, he interpreted this as my lifelong passion and pursuit. And so began a fifteen-minute conversation about sharks with absolutely no visible end in sight. It was one of those moments where you could feel the other person trying so hard to keep the conversation going that they accidentally get stuck on the topic entirely.

And while this may sound incredibly minor, there was also a moment when we stood up to leave, and I noticed the way he walked. The best way I can describe it is that he sort of…glided. Like he was gently figure skating across the restaurant floor, with more sway in his hips than I think I even have.

Dating has taught me that sometimes there’s absolutely nothing wrong with the person sitting across from you. They’re kind and they’re thoughtful. But chemistry is a strange thing.

And sometimes all it takes is one unexpected shark seminar and a figure-skating walk to realize the rhythm just quite isn’t there.

Somewhere Between the Good, Bad, and Awkward

After enough dates, you start to notice patterns. Some things matter more than you originally thought, and the other things matter less.

One of the people I dated for a little while was incredibly easy to spend time with. Our first date was at a casual restaurant over beer and fish and chips, and the first thing I noticed about him was how funny he was. We laughed a lot that night, and it felt comfortable in a way that good first dates sometimes do. As the weather got nicer, our dates turned into walks and outdoor adventures. One afternoon we walked around a park with a lake before grabbing pizza from a tiny hole-in-the-wall spot nearby. Other times we wandered through different trails just talking. He loved being outside, and I liked how relaxed everything felt.

But sometimes it takes a little while to notice what’s missing.

At some point I realized something small but strangely significant: I don’t think he complimented me once. Not my outfit, not my hair, not even the occasional “you look nice tonight”. He also wasn’t much of a texter. And while I don’t need constant communication, you do want to feel like someone is thinking about you when you’re not standing right in front of them.

And I’m not saying I’m the perfect person to date either. I’m sure I have my own quirks, habits, and things that probably make someone pause and think twice.

But that experience taught me something important about dating. You can enjoy someone’s company, laugh together, and still feel like something essential is missing. And that realization doesn’t mean the dates were bad. Sometimes it just means you are learning what kind of connection you actually want.

The good dates remind you what is possible. The bad ones sharpen your standards. And the awkward ones…well, those usually make the best stories later. I’d love to hear your thoughts too. What makes a good date stand out to you? And if you have any memorable good, bad, or awkward date stories of your own, feel free to share them. After all, the art of dating is something we’re all figuring out as we go.

As always, thanks for keeping up with Kay.