Dater X: Learning To Ask The Bigger Questions

Two summers ago, I remember sitting on a bar stool, anxiously twirling a straw in my Rum and Coke as a guy I’d been dating for a little over a month explained why he didn’t think we should see each other anymore. “Why?” I asked, stunned. He hemmed and hawed for a moment, and opened and closed his mouth sharply, as if he enjoyed the taste of the air. I could tell there was something he was wanting to say, but couldn’t quite make himself form the words.

“My parents taught me that you don’t date someone unless you can see yourself marrying them,” he said. “That’s always stuck with me. Those are words I live by.”

The wooden bar stool felt harsh and uncomfortable underneath me—almost as uncomfortable as the words coming out of this guy’s mouth. Really, he’s breaking up with me because he doesn’t want to MARRY me? Is this guy I’ve gone on SIX dates with and had sex with ONCE really talking about freaking MARRIAGE?

Looking back, here’s what I think happened too often when I was dating: I was proceeding unless something went wrong, while the guy wasn’t interested in proceeding unless things were great.

In my mind, there was no way the concept of marriage should be anywhere close to on the table. It shouldn’t even be in the same room. I mean, we hadn’t even talked about not dating other people—why on earth should he be thinking ’til death do us part? It’s MARRIAGE or NOTHING? I thought. Isn’t that a paralyzing way to think?

I left the bar that day thinking that he was crazy. That there was something intrinsically wrong about the way he was looking for love. But two years later, as I’m seventh months into the happiest relationship of my life thus far with The Young One, I finally get what that guy meant. And even more than that—I think he may be right.

Related: Dater X: I’m (Drum Roll) In Love

Let me explain.

When I was dating, as you saw when I was writing this column every week, my default mode was to keep seeing someone. Unless something bad and jarring happened—they expressed a view I just couldn’t stomach, they said or did something nasty to make me question their character, or I felt a repulsion at the thought of kissing them—I continued dating them. I could think of zillions of reasons to keep dating someone—we had fun together, I liked our banter, we had good physical chemistry, he made me laugh, he was smart, etc, etc, etc. I didn’t need all systems to be a go. One or two was enough, because feeling connected to someone felt so much better than not.

Now, I’m watching several single female friends operate this way. Something has to be wrong for them to cut the cord with a guy they are dating. I see them asking themselves after each encounter with a guy, “Are things going well enough to go out again? To text them if I haven’t heard from them in a few days? To bone them if we have a few drinks?” Because these questions aren’t very big, the answer always seems to be “yes.” It’s not that they aren’t noticing flaws, and it’s not that they are settling. I mean, part of the fun of being single is presenting the issues you’re having with guys you’re dating to your friends. (“He works 60 hours a week.” “He has a kid.” “He’s a bad kisser.” Hence, one reason why “Sex and the City” was so darn popular.) It’s just that most things don’t seem like dealbreakers because the stakes aren’t very high.

In the meantime, my guy friends seem to use a different question as a measuring stick: are things going great? Most of the guys I know default to not proceeding unless they are giddy about someone. I’m continually surprised by how guy friends can keep things casual with a girl—not talking too often, only hanging out once in a while, not getting emotionally wrapped up in them, not reading too much into sex—when I have such a hard time with those things. Sometimes I start to think to myself, “Wow, ______ is such a player.” And usually just then, they surprise me. “I met this girl and she’s incredible,” they’ll say when we hang out, with that certain gleam in their eye. While my female friends seem to be asking themselves, “Is this person good enough?” my guys friends seem to ask themselves, “Is this person amazing?”

Looking back, here’s what I think happened too often when I was dating: I was proceeding unless something went wrong, while the guy wasn’t interested in proceeding unless things were great.

Often, these two agendas overlapped for a few weeks, even a few months. But in 3 out of 4 cases, it meant that I was staying in until a guy opted out. It meant that in my years of being a single woman, I heard a lot of “I don’t think we should date anymore” talks, like that one in the bar that day. Not to mention that I experienced many a ghosting. The truth was that we just weren’t each other’s green zebra—we just weren’t the same card in this strange cosmic matching game. But because I usually left it to the guy to express that, I felt like I was always getting dumped. I felt disposable. It was damaging for my sense of self of worth and it made me feel prone to panicking for way too long into my relationship with The Young One, even though I had nothing to worry about.

Related: Dater X: I’m In A Great Relationship, So Can I Stop Freaking Out Now

Looking back, I wish in almost every dating situation that I’d taken more of an active role in determining if someone was my match. Knowing what I know now about how wonderful and nourishing and fun and passionate a relationship can be, it’s pure comedy to me the things I accepted before. Even with the guys I mentioned in this column who I felt crazy about. Like with The Architect. Sure there was a lot of good there. But I also felt like we were often jockeying for power, two sumo wrestlers circling each other in a ring, looking for a moment of weakness. Not to mention that we weren’t all that in tune in bed. Was that really good enough for me?

Or with Tall Guy. There was so much about him and our dynamic that I adored. But after the high of our first date, I noticed that we often fell into long pauses. And not pauses where neither of you feels the need to speak—pauses of awkwardness, both of us was mentally scanning our brains for things to say that the other would find interesting. We just didn’t feel that comfortable with each other. Was that really okay with me? Or, The Juggler. I recognized right off the bat that we didn’t have long term potential. Since long term was what I wanted, why did I keep going with it until he disappeared?

In each of these cases, I wonder what would have happened if I had raised the stakes. If I’d asked myself that question that seems so outlandish: could I see myself marrying this person? Each time, I think it would have helped me identify that that these guys just weren’t it for me.

I’m not exactly sure how to turn this observation into advice, for single friends or myself, should I ever be single again. See, I understand why we don’t use marriage as the bar. We don’t use marriage as the measuring stick because it feels like we’re skipping so many steps. Because we don’t want to be cliches—the girl daydreaming about what kind of frosting she wants on her wedding cake or, worse, the shrew in a “Bridezilla” episode. Because we don’t want to scare ourselves or (gasp) the guy we’re with by thinking too hard about “the future.” Because if we use that high a standard, we’ll only date someone once an eon. And of course, because we want to leave the room for things to grow and develop—which is how things often work. But that said, I would love to see my single friends—the ones who want love, not the ones who are happy keeping things casual—to adopt a different set of criteria for themselves. Maybe, “Could I see myself marrying him?” is too lofty a question. But I’d love to hear them ask themselves, “Is this relationship stellar?”

Related: Dater X: 10 Things I Did Right As A Single Woman

Remember that guy from the bar? The one who broke up with me two years ago? Well, he’s a friend now. And by sticking to his would-I-marry-them gold standard, he did find someone amazing, someone with whom he meshes 100 times better than he ever would have with me. In fact, he just bought her a ring.

For maybe the first time in my life, I’m with someone I actively want to make a commitment to. Who, when I ask myself, “Could I see myself marrying him?” the answer isn’t “maybe,” or “perhaps in a few years if ________, _________, and _________ happened.” It’s “yes.” Will this be the way things go? I have absolutely no idea—it’s far too soon to tell and I know there could be surprises of the unpleasant kind ahead. You can’t know what will happen with another human being—life is just too unpredictable—but you can absolutely know what you want to happen.

And isn’t that half the battle?