To say that dating these days is weird is redundant. Quite literally 0 of the people I’ve talked to about dating in 2014 understand it, and that’s regardless of how successful or not they are. While there certainly isn’t just one aspect that makes dating weird, personally one of the more confusing aspects is the simultaneous approach to dating that is necessary in today’s world. This means seeing multiple people at the same time, until one relationship gets serious enough that the others are ended. From all of my accounts, this seems to be the strategy for most folks, and I don’t just mean the adulterous heathens I know (JK, love you all).

I personally was never one for simultaneous dating. I’m not saying that in order to make myself sound above all you terrible people, I just say it because I never really could wrap my head around maintaining even the fledgling stages of a relationship with more than one person. This actually explains the number of girlfriends I’ve had in my life (some day it’ll be one).

The afore-made joke aside, this casual approach to dating has proved difficult to execute beyond my own personal befuddlement with it. That’s because as it turns out, for some reason I’m perfectly geared for relationships, and tend to skip the casual phase altogether. In fact, that’s how I ended up dating my last girlfriend. I went in with the intent that I need to “just have some fun and keep it light and casual.” She seemed to voice that same intent. Yet there I was, spending most nights of the week at her place, walking her dog for her, and having to call her out on the fact that while I’m certainly not complaining, what we have was neither light nor casual.

But since the inevitable implosion of that relationship, I decided to get hip with the crazy kids these days and double down on the simultaneous approach. It’s innocent enough. For me it means having drinks and hanging out with a couple of gals at the same time (feel free to imagine that the number of gals is in the double digits). There’s no pretense of exclusivity in what we’re doing. They could also be seeing other people, and it’s none of my business nor would it bother me.

This is all well and good, but since trying this out an unforeseen issue risen up. Which is that I have no clue as to when I should focus solely on one of these women, and tell the others to take a hike (in a very polite and gentlemanly manner, of course). What’s the key milestone where it starts being “a relationship?” Being a crotchety old man in a, let’s just say, 25-year-old’s svelte body, my personal standard convention is that the ‘ol horizontal shuffle is that pivotal moment. But I know this isn’t the social convention. The gravitas that sex used to have simply isn’t there anymore, and it’s something that a fair amount of people do with little to no regard towards the state of relationship with their partners. Hell, there’s times when that state is straight up non-existent (See: Tinder, Grindr, etc. etc.). It’s almost as if at this point the more intimate endeavor is a solid cuddle session on the couch.

As with all things related to us humans dealing with each other, it seems that the key to figuring out this point is communication. You need to be up front and clear with the people you’re seeing. And you absolutely have to be considerate of any differing viewpoints in both how you define the relationship you have and at what rate it’s progressing. One of the worst things in dating is when one person sees the relationship getting serious while the other person is still seeing it as a casual thing. Another of the worst things in dating is when one person does not appreciate the subtle genius that is the movie Saving Silverman. IT WAS AN ACTING TOUR DE FORCE, CARLA. THE JOKES WERE NUANCED YET LAUGH-OUT-LOUD FUNNY. HOW DO YOU NOT SEE THAT!? I digress.

I guess the answer is that there really isn’t an answer. It’s a matter of treating each endeavor as unique, and as long as all parties involved are on the same page and feelings are kept in consideration, there will be a clear moment of realization that a relationship has blossomed. And what about me? At what point did I decide that one of my relationships was at a point where I’m now officially dating her, she’s my girlfriend, and I will only be seeing her? Well I haven’t hit that point yet, but I’m sure I’ll feel it when the time is right. I mean, one of my wives is bound to divorce me at some point, right?

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