One of the most important parts of getting better at dating is being able to recognize the mistakes you’ve made. After all, you learn very little from your successes and far more from your failures. Of course, sometimes you have an embarrassment of riches…
Of course, the point of looking back at your unforced errors is to learn from them, not to wallow in self-pity about how awful/pathetic/why-are-you-even-allowed-to-leave-the-house you are. On those occasions, it helps to have a more experienced hand to cut through the chagrin and give you a detached perspective. That’s why it’s time to put my dating life back on the examining table for another Anatomy Lesson. This time, we’re going to step back into my bad old days and look at the night that ultimately changed my life. This was the night that put me on the path to becoming the man I am today… and by no small coincidence, it’s also one of the nights I look back on and experience a full-body cringe of second-hand embarrassment.
Actually, is it even possible to be second-hand when you actually lived through it? But I digress…
So we’re going to talk about the night of The Party Foul, when I snatched defeat from the jaws of victory through a unique combination of Oneitis and being a Nice Guy. As always, names and certain details have been changed to protect the innocent and guilty.
It was the weekend of my brother’s wedding. I was in my mid-2os, fresh out of another bad break-up and looking for something, anything to prop up the tattered remains of my ego and things seemed promising. The entire wedding party and assorted guests had quite literally taken over the tiny hotel where we were staying, there was an open bar and a wide assortment of attractive 20-somethings spending three days in close proximity. It was the sort of setup that all but guaranteed fun drunken shenanigans for everybody, a weekend of bad decisions and ill-advised hook-ups and I couldn’t wait to take full advantage of it.
And by all rights, I was in the catbird seat. Sure, I wasn’t the smoothest operator in the world (to put it mildly), but fate – and the wedding planner – had put me in a position where I could show off my talents. Even back then, I was a natural performer; put me in the spotlight and I’m in my natural element. I couldn’t flirt if you put a gun to my head but put a microphone in my hand and I could own a crowd. Since I was both the officiant for the wedding and master of ceremonies, the gods themselves may as well have said “here’s your moment to shine.” Outside of the bride and groom, I was going to be one the most visible guests at the wedding and that to my mind that meant that I was going to be the closest thing to a celebrity that night.
It was perfect. I couldn’t lose, as long as I didn’t fuck it up…
I actually was in a pretty good position, if I knew how to take advantage of it. I was – and still am – good at writing speeches and wedding ceremonies; funny without sounding like a performance, sentimental without being maudlin, heartfelt without being schmaltzy. Being able to take people on an emotional journey is attractive; being able to make them laugh is even more so. Being the guy who was in charge of keeping the emotions going by encouraging toasts, providing funny anecdotes and stories about how great the bride and groom were while not stealing the spotlight from them… when done properly, it can generate a fair amount of social proof. As someone with a fairly significant position during the events leading up to the wedding and in the wedding itself, I was about as vetted as one could get. I was in a position to build up a lot of metaphorical capital by showing people that I was a fun, cool guy.
The problem though is that social proof helps, but it’s not everything, and you can burn through it very quickly if you’re not careful. In my case, I was expecting being in the wedding party to do the work for me, which is not how this works. Having a position of honor only meant that I had a chance to show that I was cool; it didn’t mean that people were going to dig me just because I was the groom’s brother. I was still going to have to generate chemistry with the people I was interested in; otherwise, I was just a cool but otherwise unsexy guy.
And of course, that ignores the possibility of actively fucking up…
Over the first night, I attempted to lay some groundwork, scouting out likely prospects for a post-reception hook-up. While there were a number of potentials – certainly none that I would turn down, given the opportunity – and I certainly seemed to be getting along well with a couple women, there were few that inspired the instant lust that I was looking for. Except for one. Her name was Samantha and she was jaw drop wolf-whistle lip bite.
Petite yet curvy, with wide doe-like eyes and a Cupid’s bow mouth that left me imagining what it would be like to kiss her. It was lust at first sight and by God I was going to move Heaven and Earth to get her.
There was only one problem. My buddy Miles noticed her too.
I’ve written about Miles before: he was handsome in a Zac-Effron-without-the-muscles kind of way as well as effortlessly charming and funny and could attract women the way that cheese attracts mice. Of course, to make matters worse, he was also one of the legitimately sweetest and nicest guys you could ever meet. I loved him like a brother and there were times when I wanted to throw acid in his face.
The problem was very simple: when Miles was around, other men were basically invisible. Therefore, my plan was brilliant in it’s simplicity1: get in the first shot. As long as I established my claim, Miles would respect Bro Code and back off. In the meantime, the more time I spent with Samantha, the more she’d become similarly enamoured of me. And so I resolved to be around Samantha as much as humanly possible. If I had a free moment, I’d make a point to just “happen” to find an excuse to be around her. She’s getting a drink? Hey, I need a refill too. She’s talking with some friends? Perfect time to go over and try to join the conversation, or at least hover in the background trying to find an opportunity to interject. I’d start conversations with her and do whatever it took to power past the awkward silences and just keep the interaction going.
The only times I didn’t hover around her like a lost puppy were either because I had wedding duties or because she’d gone to bed. Oh, I’d make a point of doing other things on occasion; I didn’t want to come across as though I were smothering her, after all. But if I thought there was an opening, I took it.
The night before the wedding, I could barely sleep; I was like a kid before Christmas, too excited about the thought of unwrapping his presents. When I did finally pass out, I slept the sleep of a man who knew down to his core that he was going to absolutely destroy the bed the next night. Angels would weep to see what was going to happen in that room. Our fucking would leave a permanent impression on my hotel room like a cum-stained version of The Grudge. Future guests would be haunted by the sex that happened in that room.
There was no way that this could possibly go badly.
To be perfectly honest: this was over before it even began. The cold and hard truth was that as much as I was into Samantha, this was as much about Miles as it was about hooking up with her. As much as I wanted to sleep with her, no small part of me was seeing this as a battle between me and Miles; if I could get with her it meant that I had won. Won what? The contest that Miles didn’t realize he’d entered into by virtue of existing. This would prove something about me and my value as a person. Needless to say, it was not a healthy place to be coming from. I was basing my self-worth on a) hooking up with someone b) that my friend also wanted and c) proving I was more desirable than him as though this meant anything other than that person’s taste in men. This would, in fact, come around into biting me in the ass later on.
Ignoring the emotional unhealthiness of it all, my attempts at winning Samantha were laughable. Proximity and familiarity is one thing when it comes to attraction; the more we get to know somebody, the more attractive they become to us. This however, assumes familiarity over time, and acting like a normal human being. Hovering around them like a satellite, on the other hand is a different matter entirely. I was demonstrating a serious lack of emotional intelligence by trying to occupy all of her time. I was completely ignorant of any signals she was giving off; any attraction she might have been feeling for me was bleeding away more I cornered her. In retrospect, it would have been much better to come in, talk and flirt a little, then go on to do other things and re-engage her later. If she was interested, then I wouldn’t need to force the issue of spending time with her; it would be perfectly natural for us to hang out more.
The day of the wedding was an exercise in “hurry up and wait,” for all of the men in the wedding party. It was a constant rush of getting ready, then finding ways to fill the time until the ceremony. My brother, Miles, the other groomsmen and I killed time in our waiting area playing poker and occasionally venturing out to grab more beers and snacks. The wedding itself was beautiful and went off without a hitch. Vows were said, speeches were made and pictures were taken. And then it was time for the reception – a time that I’d been waiting for like a prisoner waiting for his release.
In the early moments, it was wonderful. My speech killed; everyone laughed in all the right places, sighed in others, and cheered. As the happy couple finished their first dances, I took to the dance floor. This had been no small part of my plan; dancing was one of the other areas where I had the opportunity to show off. My brother and his wife had chosen big-band swing for the music which was perfect for my purposes. I may only do the Awkward White Guy Shuffle in clubs, but throw in some accented triplets and I’m a devil on the dance floor. I studied swing and lindyhop in college and had been recruited to the swing team in college. Swing dancing was well within my wheelhouse. So it was my time to shine.
In fact, it became a sort of friendly competition between one of the bridesmaids and myself; once she found out that I knew how to swing and lindy – had, in fact, been going to swing nights fairly regularly – she demanded to see whether I could dance as well as I ran my mouth. She and I burned up the dance floor as we tried to one-up each other in an attempt to see who could keep up with whom. She was easily one of the best dance partners I’d ever had and it showed. People who’d known me for years told me they’d never realized I’d had that in me. I felt amazing and was having the time of my life.
So naturally, that was when everything fell apart.
I had only barely seen Samantha that evening; I’d been too busy with the ceremony and MC-ing the speeches afterwards to worry about finding her. I’d been willing to let my natural showmanship seal the deal and find her later. What I hadn’t realized is that I hadn’t seen Miles either. And when I did see them together… well, they weren’t sucking face, but there was every sign they would be. And so I did what every other red-blooded man would do2: I made sure I never let them have a moment alone.
No matter where they went, I would be there. Dark romantic corners? “Hey guys, fancy running into you here!” A slow song on the dance floor? Amazing how I’d manage to find an opportunity to be right there with them with my dance partner from earlier. I even played dirty, grabbing women I knew had crushes on Miles and sending them to drag him away so I’d have a chance to plead my case with Samantha.
And I do mean plead. Towards the end of the night, I was literally asking her to choose me over Miles. “I’m going to be honest,” she said, “you and I have so much in common that it we would be great together. All Miles and I have is physical.”
“But you’re still picking him, aren’t you?” I asked. Samantha didn’t say anything. She just smiled and patted my hand before leaving me to anesthetize the tattered remains of my ego with the handle of vodka I liberated from the bar to bring back to the hotel. That night I sat and watched couples pair off, leaving me alone with the stragglers; my dance partner from earlier, and a few friends who weren’t ready to go to bed just yet. Finally, I stumbled my way with my Absolut best friend back to my room.
Did I mention that my room happened to be right next to Miles’?
It’s hard to tell exactly where to start with this. My first and biggest mistake was, frankly, obsessing over “beating” Miles with regards to Samantha – as though her opinion on the subject didn’t matter. The fact is, she’d been interested in Miles from the jump and there really wasn’t anything to be done at that point. The way I was acting would have extinguished any hint of attraction she might have had for me; I was displaying almost absurd levels of neediness, which is the Anti-Sex Equation. By the time I was playing “If I Can’t Get Some, NOBODY Can”, all I was doing was humiliating myself. Not only was I not going to prevent them from hooking up, I was sacrificing my own ability to enjoy the rest of the night.
What should I have done? Well, to start with, not have been obsessed with proving myself against Miles. Once you base your self-esteem on how you compare to others, you’ve given up. It’s one thing to be inspired by another person’s success to motivate you to do better. It’s another when your self-worth is dependent on showing that you’re “better” than them.
Next, it would’ve helped if I had the vaguest idea as to whether she was at all attracted to me in the first place. That would’ve let me know whether it was worth my time to make the effort or to just move on and find someone who was interested. If she was, I would have done much better to be low key and divide my time amongst my friends and wedding responsibilities instead of becoming an orbiter. Giving her the space to come to me once that initial connection had been made would have made for a stronger connection and increased the likelihood of any post-reception fooling around.
And finally, I should have recognized earlier on that she wasn’t interested and moved on. There are times when persistence can work out (provided you have a clue as to what you’re doing) but a) that means playing the long game and b) you’re usually better off spending your energy elsewhere.
Ironically enough, if I hadn’t been so focused on Miles and Samantha, I’d have had a much better evening. Once you leave out the way I acted around her, I was actually doing everything right. Between being the MC and the officiant and having fun on the dance floor, I was demonstrating a lot of value. I was having fun, I was helping other people have fun and I was looking pretty darn good doing it. If I’d spent less time on beating my head against a wall and more on just enjoying myself, the night would have ended very differently. Even if I didn’t end up hooking up with someone, I would have enjoyed my night – a worthwhile goal in general.
Instead, I was sacrificing my time and dignity in a fruitless quest to get into somebody’s panties in the name of proving that I was a Real Man.
Of course, since irony, not gravity is the strongest force in the universe, there was one more slight twist of the knife to my self-esteem…
The next day I felt lower than a snake’s ass in a drainage ditch. It was bad enough that I had the sort of hangover that felt like someone had puked in my soul, but I had a pounding in my head (and on my walls) that meant I barely slept a wink.
Of course, I would later found out that some of that pounding was actually on my door. I’d actually slept through one of my dance partners’ trying to wake me up for a 3 AM bootie call.
I could barely look at Miles the next morning. Seeing a friend having hooked up with someone I wanted to hook up with was familiar enough that I just wanted to shove breakfast tacos into my face and disappear to nurse my wounds and salve my ego. Back in my room and frustrated beyond belief, I swore that this would never happen again.
I fired up my laptop and entered “How to get better with girls” into Google…