First Date Recap – The Boss

Time to un-hide...

So after months of hemming, hawing (what the hell is hawing anyway?), discussing with friends, co-workers and strangers, I finally decided I was ready to do the dating thing. I un-hid my POF profile, dusted off my lip gloss and flat iron, and waited for the suitors to come rolling in.

And much to my amazement, they did. Unfortunately, ones who came rolling in were typically lacking in something.  Specifically content. The first five messages I got were some variation on “hey”. I got a few “Hey how are you?”s which typically didn’t have a question mark, and I also received my fair share of “hey sexy/sweetie”s which, while flattering, are all so overwhelmingly lazy that I couldn’t help but roll my eyes. I had decided, though, that I would answer every message that came my way. I wouldn’t be a shallow bitch who dismissed guys simply because they look like a serial killer in their profile picture or seem incapable of stringing together a full sentence with no spelling errors on a website with a built in spell-checker. Nope, I would not be closed minded. I would answer everything that came my way because who says that the guy of your dreams doesn’t make you want to puke in your mouth a little bit before you get to know him?

Ironically enough, if I hadn’t decided to answer all messages, I never would’ve met The Boss since his profile broke all kinds of my self-imposed rules. He didn’t have a profile picture (um, what are you hiding?), he hadn’t gone to college (yeah, yeah, shallow bitch, I know. That’s why I was ignoring those rules, remember?), and his profile was about half a sentence long. Probably the biggest offense, though, was the fact that his first message to me was mocking one of the bands I listed on my profile, and not in a “I’m just ribbing ya a little” sort of way but more of “I’m a giant douche who has nothing better to do than troll people’s profiles and send them inflammatory messages designed solely to belittle and insult” kind of way.

Attractive, right?

In any case, I’d said I would answer back everyone, so I shot off something short, and somewhat snippy. And then the oddest thing happened: his reply was well thought out, articulate, and nice. He mentioned bands he liked and gave an argument as to why the band I liked wasn’t as good as some others from the same era (not that I’m changing my mind, but I appreciate a good argument). He also sent a link to a picture of himself. He was not necessarily my type, but he wasn’t bad looking at all.

We messaged back and forth for a few weeks, and finally arranged a date. The plan was to meet on a Saturday evening at Dave and Busters for drinks, dinner and conversation. I wore what I thought would be a nice first date outfit that said “I’m flirty, but you’re not getting any,” flat ironed my hair, and set off on my first date in over three years.  I got there early so I could go to the bathroom and make sure that that I wasn’t a sweaty, shiny mess after walking across the football field sized parking lot, and then stood awkwardly by the front door waiting for him. At ten minutes past the designated meeting time, I texted and asked where he wanted to meet me. His reply: he was there and UPSTAIRS. Huh? There’s no entrance to the upstairs, meaning he’d have had to walk past me to the stairs or elevator at some point. Okay, well, whatever. I was too nervous, and had put too much thought into my outfit to get pissy and blow it off at that point, so I proceeded upstairs to meet him.

He looked exactly like his photo, thankfully, but I knew in that first half second that I wasn’t attracted to him. (Also, I should add that although he claimed to be 5’8”, I was wearing flats and we were the same height. Unless I grew three inches over night, I think he might have participated in some height inflation.) So did I sit down, have a beer, and then gently make an excuse and bail? Nope. Instead, I decided to give him a chance. Attraction can grow if you really like a person, so I figured I shouldn’t judge too quickly. I’d flat ironed my hair, after all.

In the end, the date was okay, and was a nice way to get back out there.

Positives:

• I had fun playing the games, and he didn’t get pissy when I kicked his ass.

• The food was good.

• He was polite and had good manners.

Negatives:

• He came across as somewhat patronizing, and actually I found myself wondering if he was used to dating stupid women. For instance, when I won at something he would congratulate me in that tone you use when your dog successfully rolls over to get a treat. Also, he loved explaining things in a long-winded sort of way, regardless of whether or not I knew anything about it. At one point, he took it upon himself to explain (in the longest way possible) how gentrification forced residents out of their homes, despite the fact that I told him that I had lived in the area we were talking about and knew something about it. Maybe he was nervous, but it rubbed me the wrong way.
  

• He spent too much money. The first few drinks he bought (despite my admittedly token protests), were nice. Then he bought an appetizer. Then he paid for all the games we played. Then he bought dinner, which would’ve been something way pricier if I hadn’t insisted that we go get a burger. While I definitely appreciated it and had a good time, when a guy spends that much money on a first date it seems like he’s either showing off or expecting something. It was too much too fast.

• While I appreciated that he was polite, there was no flirting at all. No compliments, no mild, but unmistakably sexual comments, no hand-holding, nothing. We hugged once upon meeting, and once at goodnight. Not that I wanted to be uncomfortable or pawed at incessantly, but an attempt to hold my hand or a “you look really nice,” would’ve been welcome and on par with what I thought happened on a first date.

• I think he might be clingy. As we were saying good night, he asked if I wanted to go out again the next day. Um, no. He then proceeded to call me ten minutes later when I was on my way home, and then texted me at midnight to say he had a good time. I get it, thanks. Chill out.

What I learned:

• Never agree to dinner on a first meeting. By the time he was considering where we should get dinner I was ready to head home. We spent like six hours together, and honestly after three I could’ve called it a night. Also, now I feel bad because I kind of don’t want a second date, but I feel like since he spent a few hundred on me, I should at least take him out for a $14 steak or something.

• I need to not converse with people that I don’t even have a wee bit of attraction for. I thought chatting long enough would change his attractiveness level in my eyes, and while that has happened in the past, it feels like I’m wasting both our time if there’s not even a little bit of physical attraction there.

• Never do shots on a date. The first thing he bought me (unprovoked, mind you) was a shot of Patron, followed by a beer, and a Tuaca bomb. Luckily I’d nibbled a bit before I left home, but I was still pretty light-headed for the first hour or two. Not only is that a number one no-no in the single girl dating handbook, but it  also makes first date conversation a bit more difficult.

Overall I’d give the date a B-. It was nice to get back out there, and the games and everything were definitely fun. At the same time, there was zero chemistry, and when I’m falling asleep at the end of the night, it’s probably not a good sign.

(Side Note: so two posts in one day is crazy, right? I'm procrastinating right now, and wanted to write about this while it was fresh in my head. In other words, don't get used to it!)