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The Math of an Awkward Goodbye

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I have a really hard time ending dates. Painstakingly hard. I might as well be trying to perform a root canal on a penguin with a pudding cup as my only tool. Typically a date has a formula of sorts: we are going to do X (in which X = an activity that has a set amount of time), and if we like each other we might try Y (in which Y = something different in both of our heads at the time of conception but we would come to an agreement based on who decides to continue the date), and we are then going to Z (in which Z = part ways in a fashion). This all works quite well in the normal datingverse – the one where I’m not here today, gone tomorrow. However, in the land of fifty/fifty, these equations seem to be thrown to the birds.

My biggest issue is simply ending the date. Despite having the X factor down pat, the Y factor is tricky: mostly, it’s a challenge to get locations on the fly that will allow filming. Which means if we don’t plan for Y in advance, then there will be no Y unless we accept that filming won’t be happening, which we don’t like to accept. But if we do plan for Y in advance and either me or my date don’t want to do Y for whatever reason, weaseling out of Y becomes tricky, nay impossible. In short, these dates don’t have as clear an end – Z – as dates back home.

The lack of a known Z is partly based on the factors above, but also tangled up in the concept that I’m only in town for a day, and for some guys this is their one chance.* And that there’s a camera or two involved.  And a Megan. Due to the latter two complications, I think dates are looking to me to blow the final whistle on our time together (which is so weird. I want this to be a date-ocracy; I actively hate being a date-tator).

Regardless, Z is always the most awkward moment of the date. And mind you, these are dates where inevitably I have said something bizarre, the guys are thrown off their game based on the cinematic aspect of the date, and at some point Megan has given us a direction such as why don’t you walk into the coffee shop, wait a beat, then walk out, and then do it again just in case, meaning we’ve entered and exited a building twice for seemingly no apparent reason. (Onlookers enjoy this. I call it burning extra calories.)

I just don’t know how to end a date well. Handshake? Wait, no, I hugged you when we met so that would be weird to downgrade. Hug? Wait, what if we had a great time but we hugged in the beginning so where do we go from there…a lingering hug? And what about words…what could I possibly say to someone I won’t be seeing again for awhile if ever? Meh.

Megan has a theory: that of course saying goodbye is awkward. This is the first time you’re ever saying goodbye to this person, and thus you don’t know how to do it. With friends you’ve known forever, you’ve said goodbye a gagillion times and it’s a natural event. But with a first date, you’re figuring each other out, which includes figuring out the au revoir aspect of your potential relationship.

She has a point. But I stand to reason that if I’m good at saying hello to a first date sans feeling squeaked out, there’s a distinct possibility the same can be done for goodbye and the only thing standing in my way is me.

Suggestions for saying ciao on a first date welcome.


*The one chance concern has been brought up by a few dates, and it’s a concept I find interesting. We live in a digital age that has airplanes. Contact and connecting might be a challenge post date, but it’s not out of the realm of possibility. Internet, folks. Facetime. I’ve had some oddly satisfying relationship-type-things that have played out mostly via screens and letter writing. Point being, if we like each other, there’s no reason this has to be it. I mean, when I’m done with all the dates.

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