Guys, Here's How To Tell When You Should Make Your Situationship Official

You've started seeing a new girl, and life is good. You're seeing her practically every weekend, you're sending her the occasional text at work and you're still feeling baffled that she's seen "Gladiator" as many times as you have. Yeah, it's one of those situations.

When things are going so well with someone new, it's easy to go with the flow and not worry about things like titles, exclusivity or making it “official.” Eventually, there comes a time when you start to wonder, “Am I dating this girl, or are we just hooking up?”

Of course, she's been wondering the same thing for weeks by the time you got around to thinking about it. Maybe she's started dropping hints? Probing a little deeper into your personal life? Or maybe, she's started the dreaded conversation all guys know is eventually coming: “So, where do you see this going?”

Making it official can be stressful. It's not always easy to know when you're ready to focus on a relationship with someone you're still learning about. The thing is, people tend to overcomplicate the process by excessively stressing or trying to plan the moment when you can drop the relationship bomb in the perfect way. (Central Park at sunset, street musicians, a summer breeze … Stop me if you're getting nauseous.)

A couple of years ago, I was seeing a girl for a month or so when that moment struck me out of left field. We were walking down the street when a homeless man approached us asking for change. The man engaged us in a dialogue that quickly led to, “Oh, is this your wife?” When I quickly answered, "No," he rebutted, “Your girlfriend?”

Boom, he had me. In an instant, I had to decide if this girl I had been seeing casually was, in fact, my girlfriend. This guy on the street just Dr. Phil-ed the sh*t out of me.

But you know what? The answer was simple. “Yeah, she is.” I gave the guy the change in my pocket, and we moved on. That was it. There was no drawn-out conversation, no stressful pondering, nothing. It was easy. We dated for a few months after that.

When the moment was put directly in front of me, I had to decide. And the decision was simple. Why overcomplicate it?

Conversely, I've been in relationships that went on for too long before we have that "define the relationship" moment. It ended up being a giant elephant in the room, with her obviously wondering when I was going to bring it up, and me not being sure I wanted to at all.

It's just like when one person in a relationship says, “I love you” before the other one is ready for it. Try as you might, but there's no squeezing that monster back into Pandora's box. In the same way, when you let it go too long before talking about making it official, things can get awkward in a way that's hard to reverse.

My current relationship is by far the best I've ever been in, and it's also the one with the most ridiculous story of how we made it official. We had been seeing each other for a month or two, and we were at that stage of not being able to keep our hands off each other. One night, in the middle of the act, we may have tried a move that was a little too acrobatic for our inebriated states of mind.

The smacking sound of flesh on wood interrupted the moment, and when the lights came on, all I saw was blood everywhere and a gash on the forehead of a very embarrassed girl. While I was bandaging the wound between bursts of laughter from both of us, I said something about never having injured a girlfriend like that.

As it turned out, she had recently begun thinking about making it official with me. So, between squirts of blood, we did just that. The rest is history.

I'm going to remember that moment for the rest of my life not because I spent weeks planning it out, checking the weather and deciding on the right moment, but because it happened in a way that only could have been done by me and her. It was organic, and it was an absolute testimony to what our relationship is: fun.

For any guys out there seeing a new girl, having a blast and wondering when it's time to make it official, I challenge you to forget the plans, the stress or the question of when it's the right time. Instead, enjoy what you have going on with her and let the rest fall into place. I promise it will happen naturally, and it will be fantastic.