A Whole Lot of ‘Less’

This is the story of my first first date in 2 years.

I met this guy – let’s call him Paul – at a bus station. We were both on our way back from NYC and started chatting in line while waiting for our bags to come off the bus. He was pretty good looking in the bus station flood lights. Paul told me that he was moving back to the area from Long Island. He asked for my number and on a whim I gave it to him.

The next day he called and asked if I wanted to meet him for drinks that night. I picked one of my favorite bars and a time when it was still sunny outside for us to meet up. Since this date was with a total stranger (defined as not knowing his last name) I took all the necessary precautions of picking a safe, public place to meet, having a friend ready to down to the bar in an hour, parking in front, etc.

This is more like it!

I got there first, picked a high top near the bar, and got a beer. Paul got there on time in a crisp new white tee (I knew it was new because the folding creases from the packaging were visible), khaki shorts, and boat-ish shoes with no socks. He was about as good looking as I remember. Paul comes over and gives me the Long Island cheek kiss hello. He seems a bit frazzled and wants to start talking but I tell him to get his beer (after giving some recommendations) before we talk.

Some highlights of the conversation that follows:

“Sorry I’m sweaty; I had to walk from the bus stop under the bridge. Some guy had to help me find the bar.” OK so he’s car-less – no big deal. He just got into town, it’s better for the environment, I’m not that shallow.

“I’m staying at the City Mission right now, unless I can find a couch to crash on, like yours?” Hmm…. homeless? Everyone has a rough patch or two. I promptly lie and tell him that I have a lot of roommates that would not like a stranger sleeping on the couch. He asks where I live (because he’s looking for an apartment obviously) and I wave my arm in the general “up the hill” direction and change the subject.

“Oh yeah, I’m waiting to hear back about the job tomorrow. I know a guy who needs someone to deliver tires. He’s going to get me a job.” Jobless too? At this point I’m thinking three strikes you’re out, but my beer is only 1/2 way gone so I hold out for more of the story.

Apparently Paul had just escaped an almost drug bust on Long Island. He is also a writer who is waiting to hear if Seth Macfarlane is going to buy his script for a cartoon – and I forget the rest of the story.

Paul and I order soft pretzels (because he is drunk off his one beer) and he asks the waitress if they are hiring. She brings him back an application and – this is my favorite part- he starts to fill it out! On the table, during our date – after asking me for a pen! He fills out a couple lines and says “this isn’t cool huh?” I shake my head and reply “Not cool”.

Paul: folding up the application “I bet you really don’t want to make out with me now. Or maybe you do?”

Me: “Just eat your pretzel Paul”

At this point he realizes I’m only 23 (he’s 32), he also realizes that I’m not going to give him a place to stay, a ride to the mission, or pay for the whole pretzel (we split it, $4 each). I’m thinking about how ridiculous this whole situation is and praying that he doesn’t get the job at one of my favorite bars.

We end with a hug and Paul promised to keep me posted on his job hunt. I wish him luck, start to drive off. I watch him go into the bar across the street to get another application. *Face palm

I called my mom to let her know that I was home safe. She asked if he followed me home, I said that unless he was running after my car I was safe. I never heard back from Paul.

My friends still get a kick out of the time that Chelsey went out with a homeless guy.  I’m convinced that kind of stuff only happens to me! On the bright side, I will forever win the “worst first date” game!


5 thoughts on “A Whole Lot of ‘Less’

  1. Wow, that’s a bad date!! Very funny though, how he even started filling out the application, like he’s thinking, maybe if I prove I’m looking for a job by filling out this application, I’ll have a chance… Thanks for sharing 🙂


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