This Valentine’s Day, I found myself in Champaign, Illinois. I was there recruiting at the University of Illinois, but I decided to stay for dinner at a highly-rated BBQ restaurant called Black Dog. Needless to say, I was the only “party of one” they served that evening. I eat by myself plenty, but this time I ended up not really being alone.

While perusing the menu, a jolly older couple (I’d guess 60's or 70's) asked if they could stand at the bar next to me while they waited. Coincidentally, they ended up getting seated there, and they were amongst the friendliest people I’d ever met. John was a photographer who had lived in Champaign all his life; Pat was raised in a small town nearby. We spent the next hour and a half talking about their son, print journalism, my startup, Boston, pets, and even the future of email.

I spent most of the 2.5-hour drive home thinking about John and Pat, but it wasn’t because of the content of our conversation. When they sat down, I joked that I was crashing their Valentine’s Day dinner. John beamed, “Ha! After this long, we’re just celebrating because it’s Friday.” Throughout the entire evening, I was struck by how much they genuinely enjoyed each other’s company. It was clear they were happy together, not just content. More than anything, John and Pat were each other’s best friend.

I’ve been thinking about relationships a lot since I went on a cruise with my parents over Thanksgiving. I didn’t have Internet access, so I spent the majority of my idle time people watching. Later on, I made this note:

It’s as people age that I think this starts to become most apparent. In our 20's, our careers, goals, lifestyles and personalities are all malleable, and it’s easy to believe that our trajectory for those things is going in the same direction as our significant other. In older couples, you start to notice that some people have an indescribable chemistry — a true joie de vivre — whereas others seem like they just happen to tolerate each other for the companionship. I imagine they hit it off early, dated for awhile, and even though they were never enthralled with each other, there was no compelling reason not to be with them. Lulled into the idea that “workable” is, well, workable, they settled. 30 years later, they sit across the table making small talk about the food.

Human beings are uniquely social, and I think a fear of loneliness can often take priority over a genuine desire to be with someone. Reflecting on the relationships (i.e., not just casually dating anymore) of people I know, I see the seeds of the same dichotomy. In some cases, it’s just so mind-blowingly obvious that two people are right for each other. When you see them together, they bring out the absolute best in each other. In most cases, though, it seems like they’re just companions for loneliness. It works, and in many cases you could even say they love each other, but they’re more or less the same people as they would be independently.

The thing is, the latter type of relationship can actually be really dangerous. Being single encourages you to be outgoing and meet more people — we have an evolutionary desire to stave off loneliness (and the prospect of future loneliness). When you get into a committed, exclusive relationship with someone, that imperative goes away and you don’t try as hard. At the same time, finding love is in many ways a numbers game. You just never know if or how well you’re going to click with someone until you try. The only way to find out is to meet lots of people or get really, really lucky.

That’s why I just can’t imagine being in a serious relationship with, let alone marrying, anything less than someone I can consider my best friend. It’s unfair to both parties because it prevents both of you from finding that person. That doesn’t mean I think we should hold out for perfection — no one’s perfect, and chemistry rarely makes ANY sense. Frankly, most of the girls I’ve ever had feelings for have frustrated me to absolute wits end at some point or another.

But I do believe there’s one way to tell if you’ve made the right choice: on February 14 this year, did you celebrate because it was Valentine’s Day, or because it was Friday?