That transitory time that comes at the end and the start of the year is a time of reflection for many. I have found this to be especially true as one week after New Year’s Day is when my birthday falls. Seeing that this week I celebrate another trip around the sun, and also entering my mid-30s, I’m being a bit more reflective than usual. With that in mind, the time has come to tell the tale of the worst date I ever went on in my entire life.
If you’ve been with me and this column throughout its entire existence, then you most likely recall that writing about the woes of love and romance was something I went to quite a bit in the early days. I began this column when I was 21, I’m turning 34 this week, and I talked about it often as it was where I found a great deal of humor in my life to draw from. As I got older I thought to keep writing on the subject seemed a bit “sad.” So I stopped. Yet, I feel this story is one worth telling as, A: it was truly boggling, and B: during all of last year I had friends saying to me “when are you going to write about that?”
Allow me, if I may, and I can as this is my column, to set up a little bit of a timeline for the events that are about to unfold. Dating has never transpired anything that worked out for me. I used to go through life thinking that you just live your life and do your thing and it all sorts itself out. Then I got older and saw more people I know fall in love, marry, have kids. I then found that every single time I attempted to go after this “happy ever after” we strive for, that I would fail and fail spectacularly.
Eventually, I came to the conclusion that whatever it is people want I don’t have. The downside of being one of a kind is that you aren’t easily filled away into whatever filing system people use internally. I’ve often felt that I was too normal for the weird people and too weird for the normal people. If you’re wondering how I view myself, I will gladly call myself an eccentric introvert whose tastes are a bit all over.
As I aged I found myself ping-ponging back and forth between “it would be nice to have someone” and “screw it! I’m amazing and woe unto those who don’t appreciate my brand of hip.” Yet, we as a society think something is wrong if you’re not in a relationship or trying to find one or haven’t achieved X things by the time you reach Y age. So it came to pass that during 2017 I found myself on Tinder. I got on there reluctantly, but it seemed to be how you met people. During the late hours, I would swipe away on people who seemed my type, always finding myself surprised when we matched.
There were a few I would talk to, one out of Asheville seemed especially promising. We started following each other on Instagram and then the chatter stopped. I guess my posting about The Monkees got to her, but I wouldn’t want to date anyone who didn’t like The Monkees. So again at night I would fire up Tinder and start swiping. Reading profiles of people, seeing what they were looking for, and being reminded again that nothing about me is what people want. It was a depressing affair.
But one night I did match with someone and the talking went well! She was my type. Artistic with good taste in music. We decided to meet up, like you do, to see how things went in person. We talked for two and a half hours and it was great. I sat in my car afterward, a smile beaming across my face, slightly dumbfounded that it went so well. There was texting, more chatter, and we met up for a second time. I later asked her out to dinner, and the place and time were set.
This, my friends, is where the story falls apart for our hero. I was giddy the day leading up to the date. I did my usual “Andy’s riding high” morning routine. Singing along to Sinatra and Fred Astaire loudly in the shower. The evening came, and off I went to the restaurant of choice. I arrived early, as I do with practically everything. I got a table and nervously checked Twitter on my phone while waiting. She arrived, I saw her walk in the door and start to approach my table—with two other people.
The classic tale of “she brought a friend” was one-upped in a most spectacular manner. She not only brought a friend, but she also brought her sister. I never felt such confusion in my life. Was I on a prank show and didn’t know it? Was Steve Harvey going to suddenly appear and say “Let’s play the feud!?” I sat there and was my normal self for the first part of the meal, then I mostly turned quiet and spend the rest of the time feeling like an awkward fourth wheel at a party I wasn’t invited to.
I realized that even by the standards of bad dates I had been on, this one was epic. A legendary bad date that will stand the test of the time and be passed down from generation to generation. If they handed out Academy Awards for bad dates, this one would have swept the ceremony. I easily could see myself walking up on stage to a standing ovation to accept my Oscar for “Worst Date.”
“Wow. What an honor! Truly, I never thought it would happen, but here we are! Dreams come true, kids! OK. Wow. I didn’t prepare anything. Uh, I’d like to thank Mom and Dad for their support, all my friends. My team over at Andyland Industries, they’re the absolute best! I want to thank everyone at Tinder for bringing this cast and crew together. Oh, and how could I forget, the one this date couldn’t have happened without. Big ups to NAME REDACTED, for really taking the charge on this.” The music would then start to play. “Oh, crap! They’re playing me off! Uh, I know I’m forgetting people, but really, thank you to everyone and thank you to the academy! Good night!”
When the family reunion I didn’t know I was going to had ended, I sat in my car for half an hour processing what had happened. I did what I always do, try and figure out where I went wrong and put the blame on me. Was I not clear enough that I was intending this to be a date? Does asking someone out to dinner not count anymore as a date? I was confused, but I wasn’t confused about one thing. I took my phone out of my pocket and deleted Tinder. I was done. I haven’t gotten back on any kind of online dating since.
When my thinking was done, I drove over to a friend’s house and we sat around trying to dissect the evening. They were as confused as I was, as were all my friends who I told this story to. I tell you this not as I want pity or sadness, but for the cathartic nature of sharing a story like this. Frankly, I am still a little bit perplexed by it all.
Despite not being on any dating app since I did go on a couple of other dates last year, but nothing panned out. I’m not really planning on trying in 2019—never say never, but I’m a bit burnt out on it all. Perhaps I’m just destined to be the world’s fun uncle, that would make a lot of sense as I am a direct male line descent of Rich Uncle Pennybags, The Monopoly Man. It was her loss, after all. If anything, I am a bloody delight and my skills are making a French Omelette are rather good. C’est la vie. See you next week.