"We're Not Really Dating" and Other Bad News

While far from being the worst thing a person could hear, it always breaks my heart when the newest object of someone's affection lets them in on the awful truth about their current situation.

You know what I'm talking about, and I'm sure we've all heard more than enough versions of it.

"Actually, there is someone else, kind of..."

"Well, I have a friend, I guess you could call it..."

"My boyfriend and I have an agreement..."

"Well, technically we're not dating..."

"We're not going out, but we have an arrangement..."

You get the idea. Nothing dampens the sweetness out of a new relationship like finding out that you're a sideshow to the regularity of an old relationship.

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For the record, this is not a condemnation of testing the waters, exploring your options, dating around, juggling multiple relationships, trial-and-error, blatant whoring, or any other method of finding the right person and right situation. "You do what you gotta do" is as good a motto as I can think of.

But what I never understood (although, in a way, sort of envied) was how some people can do it so effortlessly.

A girl I know found out that the guy she'd been seeing was also dating another girl - and had been for the better part of a year. She stuck with him for a few months, but when it ended she told me that the other girl never factored into the equation.

"She took a lot of the pressure off of me, that's for sure," she told me. "I didn't know anything about her and didn't really want to, and he never talked about her. I was the fun girl. Or at least I let myself think I was."

On the flip side of that is what a guy my age told me about the girl he was seeing who had a live-in boyfriend: "Easy action, or so I thought. We were going nowhere and we both knew it, which was great at first, but I was kind of glad when she dumped me - it's kind of depressing knowing that the clock is ticking, even if it was half-assed the whole time."

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So how does anyone get over that? It might sound a little old-fashioned, but I always thought it was better to let a relationship live and die by its own merits and faults and strengths and weaknesses, not by what some outsider in a low-lit room is better or worse at.

If you get together with person A while seeing person B, what's the proper etiquette for scheduling? "I'll go out with you on Mondays, Wednesdays, Fridays, and ever other Sunday. My current boyfriend already has me Tuesday, Thursday, Saturday and the 1st and 3rd Sunday of the month, and if there's a 5th I get it to myself."

How are jurisdictions decided? Do you really want to know if they went to dinner the other night at this exact same restaurant you're sitting in right now? Why? Why not?

How is precedence determined if both want to see you on the same night?

What's the courteous time to allow between sexual encounters with person A and person B? Does it bother you that this person you like might be at your house fresh from some stranger's bed? Why? Why not?

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Difficult questions, yes, and maybe a little stupid - but questions that need to be asked all the same.

Such is life when you're looking for a girlfriend and not a custody battle.