There are some people you are just destined to have an awkward time with. This story starts with a FaceBook friend’s status update “I have a free appetizer, dinner, dessert, bottle of wine, and comedy show if you want to join me tonight.” (It was some sort of coupon deal he bought and forgot about.) For a moment I forgot the details as to how I know this FaceBook friend. I “liked” the status and about an hour later remembered I obviously have nothing better to do on a Monday night. I send him a message saying that if he doesn’t find anyone and lets me know in the next fifteen minutes before I leave work, I’ll join him. Hey, he said “free!” He doesn’t respond, so I tell him I’m gonna head home. I get to the train and I’m an idiot. Don’t ask me how in over two decades of using turnstiles I forgot what I was doing, but I didn’t walk through the one I’d scanned my fare for, and got locked out for 20 minutes. Obviously the train workers are unwilling to help me. They suggest I go to another train station, which would take me 20 minutes to walk to. I actually have been out of it a lot lately. This morning I was holding my bus fare and walked right on the bus still holding it, forgetting to hand it over, with the bus driver yelling at me. I hear my train and know it will be another 40 minutes until it comes again. I open FaceBook on my phone. My phone sucks. I mean it works some of the time, but not always when I want it to. But why would I get a new one? I hate these new fangled phones everyone has. Can’t stand them. So, I have this phone that works some of the time. I see that the FaceBook friend has messaged me about fifteen minutes earlier, “Shit, sorry, well if you haven’t left work yet, feel free to come.” I message him, “I could come actually, I missed my train, text me” and send my number. I’m not sure why I thought textmessages would be easier. After it takes me 15 minutes to look up the directions to the restaurant on my phone, I can pass through the turnstile and head over.

I stand outside the place for fifteen minutes. Sure, I was early, but my phone also decided to stop telling me the correct time. It was stuck on 6:03 for ten minutes, and it took me about ten minutes to realize it. I haven’t received any textmessages and I’m back on FaceBook not seeing any messages. I have enough time to start day dreaming and I remember how I met this guy. Over six years ago this was one of the first guys I ever met through a dating website. Our date turned into fourteen hours long and ended with more alcohol than it should have, but the night is hard to remember. I head into the restaurant and see him sitting down with an open bottle of wine on the table. His hello seemed like I caught him off guard. We have some awkward catch-up conversation. “So how’ve you been? What have you been up to?” he asks me about eight times. He says he texted me, and I tell him I didn’t get it, which is true, as my phone has only just remembered it’s also supposed to function as a clock. I’m not even sure I’m over missing my train at that point, and we start to chat. Mostly I start telling him my horror stories of running into crazy people while riding the train, and he’s laughing a lot. I start to feel like I’m in the middle of a bit when he actually tells me I should be on stage. Honestly, that part made my night. He wound up laughing more at what I said than the comedians on stage. It made up for the whole awkward mess.

So the awkward part, as we’re talking, bits and pieces of the last time I saw him come back to me. It’s like that drunk fog where just pieces of the night remain in your memory, coming back as flashes of moments in time. “Do you still have a dog? The fluffy dog?” I ask. He does. “Wow, I remembered you had a dog! I remember because I remember it coming over to me after…” I stop. Yes, after I slept with him, told him what a mistake it was because I’d had too much to drink, I remember his dog coming over to me. I swap the conversation in the middle of my sentence, “So, how long have you been with your girlfriend?” remembering seeing “in a relationship with so and so” on his FaceBook. Yeah, that wasn’t an awkward segue. As if he hadn’t finished my sentence in his mind already.

So, after the show, we give each other a quick hug goodbye -that was really more of a gesture of a friendly hug goodbye, where we barely touch each other, rather than a real hug, and I head home. I look at my phone and see I got a textmessage halfway through the night with him. It was an apology that his friend was coming to split the dinner with him instead and he hoped I hadn’t gone out of my way. He’d actually sent this message before 6pm. So his friend –who hadn’t shown up- was either supposed to show up, didn’t, and then I did, so it sort of worked out, or his friend didn’t exist, he made it up so I wouldn’t come, perhaps to avoid explaining to his girlfriend the dinner, wine, and show he’d just shared with a girl he once dated and slept with, and then I showed up. So basically the first time I meet this guy, I accidentally sleep with him, tell him it’s a mistake, get over the awkwardness of that and “never” see him again, only to go on a date I wasn’t exactly invited on with him when he’s in a relationship, six years later. Yeah, I’m doing great. But hey, free steak dinner with wine, comedy, and a compliment from a used-to-be-overweight-when-I-dated-him, now pretty hot and in-shape dude. And now I can hide from this awkwardness and go back to “never” seeing him again!