May 24th, 2004: The Worst Date of All Time, The Complete Saga

Sorry to post this again so soon, but I just realized today is May 24th -- the three year anniversary of "The Worst Date of All Time." I wanted to commemorate this historic date. The two chapters of this story were some of my most popular recent posts, and I had several people request it as one big essay they could pass along to friends and other sites. Thus, here's the entire saga. Enjoy my misery again...for the first time.

Three years ago, on this very night... 

Every time I tell this story, it comes up in the same way:

CHUCK: Pat, tell Rachel the story about the worst date ever!
RACHEL: Oh, I've got a "worst date ever" story too!
CHUCK: You better tell yours first or you're gonna feel pretty fucking stupid when he finishes his.
RACHEL: OK, so first off, he picks me up and he's wearing plaid pants. Can you believe it? Plaid pants!
ME: (bellowing Wizard of Oz-style) SILENCE! For I truly went on..."The Worst Date Of All Time."

I finished my first day of orientation for the NBC Page Program. My pockets were full of important papers and forms I couldn't wait to fill out and return to make the job official. My heart was full of Spring, my boxers were full of possibility. My dream job, a date with a real live woman...yessir, everything was comin' up Walsh!

I was to meet Jessica at 30 Rock's "Rink Bar," the ridiculously overpriced tavern they put up in the summer months when the ice skating rink shuts down. When I got to the bar I noticed Jessica was talking to a guy. When she noticed me noticing this, she ran over to me. "Hey, what's up!" I said with a smile and opened my arms for a hello hug. She did not return the hug and seemed extremely serious and nervous.

JESSICA: Um. So look, this is really weird. You're gonna hate me.
ME: What is it?
JESSICA: My boyfriend's here, he wants to meet you.

Cue record player screeching to a stop. Eight months of hanging out, there had been no mention of a boyfriend.

ME: Your...what? Who?
JESSICA: My boyfriend. He's all jealous I think, and he just wants to say hello. Don't be mad.
ME: Don't be mad? I'm not going on a date with you if you have a boyfriend.
JESSICA: No! Stop it! I want to go! I really really want to go.
ME: Well here, take the tickets and go with him.
JESSICA: I want to go with you!
ME: This is bullshit, Jessica.
JESSICA: Don't be a jerk!
ME: Me?!

And then he turned to face me. The boyfriend. A big, gelled, fratty douche who, at FIVE PM was so drunk he could barely walk. He was throwing back beers with two equally douchetacular buddies, and all three of them were pointing at me and laughing. Douche began to stumble his way over to me.

ME: I'm gonna get going.
JESSICA: What? No! Just meet him real quick and then we'll go!

Douche approached and slapped a hand on my shoulder. His voice was raspy, his breath smelled of Heineken and asshole.

DOUCHE: So you're taking my girl out, huh?!
ME: We were going to go to a concert, yeah.
DOUCHE: Sounds like a date.
ME: Nope.
DOUCHE: Sounds like a fucking date, dude! I don't know! You tell me!

I didn't respond.                                                                                                                        

DOUCHE: Jessica tells me you're hilarious.

I didn't respond. He moved closer. 

DOUCHE: You don't seem that funny.

I didn't respond. His mouth was up against my ear now.

DOUCHE: Say something funny!

I gently pushed him away from me and smiled.

DOUCHE: Yeah, you're fuckin' hilarious. Have fun with her, dude.

Douche stumbled back to his friends, who had watched this exchange and welcomed him like a hero. I pulled Jessica aside.

ME: Look, seriously, take the tickets. I'm not going.
JESSICA: Are you uncomfortable?
ME: Of course I'm uncomfortable!
JESSICA: Alright, we'll leave then. He's an asshole.
ME: He really is.

And we walked off. You're probably wondering why I went on the date. I really did like the girl for starters, but at this point it was more to spite Douche. She didn't even say goodbye to him. We just left, with the guys catcalling after us. Can you think of a more stressful and disappointing way to start a date?

Let me just assure you that the night will get progressively worse, eventually deteriorating into some sort of Kafkaesque nightmare.

We took the subway down to where the concert would be held. She wanted to go to this fancy-style restaurant, which made me very nervous about the state of my financial affairs. Immediately, the waiter approached and asked if we'd like some wine.

JESSICA: Sure!
WAITER: Excellent. And bottle or glass?
ME: Two glasses is fine.
WAITER: A bottle is the better deal, especially if you're going to drink a lot.
JESSICA: Let's just get wasted!
ME: OK, we'll take a bottle.

I wasn't asked what kind of wine I wanted, but I could tell when it arrived that it was a bit more pricey than the "Night Train" I was used to drinking. As Jessica drank she got more and more open about how much she hated her boyfriend, what a dick he was, how depressed she was about her whole situation.

ME: So I've known you for months, I had no idea you had a boyfriend. When did you guys start going out?
JESSICA: Three years ago.
ME: Oh. And you're on the outs, or --
JESSICA: We live together.
ME: Ah.
JESSICA: We don't even have sex anymore.
ME: Oh.
JESSICA: I like you, Pat!
ME: Great. I like you too.
JESSICA: No, you don't. Do you really? Like, really?
ME: Hey, pass that wine!

We drank some more, and ordered food. The check came, and as long as I live I'll never forget this total: $137.50. I had just started a new, remarkably low-paying job, and didn't have this kind of cash. In fact, I had taken $100 out of the bank that morning in hopes that it would cover me for both the date and through the coming week to payday. This check hit me like a thunderbolt, especially considering I had already blown $50 on the concert tickets, and especially especially considering I was now not technically on a date at all, but a friendly outing with a girl in a relationship. I eyed Jessica harshly, praying she would at least make the reach for the check. Just give me the reach!

Obviously, this is a Dutch treat situation, no? She made no such attempt. Since I had asked her out, and I am (at least to a girl's face) a gentleman, I bit the bullet and paid the check. I knew I didn't have enough in my bank account, so I had to put it on my credit card. (This may have been the first incident leading to my now legendary debt). I started to get up from the table. "Stay there!" she yelled at me, a bit louder than necessary. The wine was taking hold.

She walked around the table and sat down right next to me, the kind of thing you see sometimes in public and hate. She began kissing my neck and playing with my hair. It was all very awkward. I checked my watch. I told her we should probably get over to the show.

When we got to the box office, I noticed that Violent Femmes tickets had just gone on sale. The Femmes are one of my favorite bands, I had never seen them live, and didn't know if I'd get another chance. I checked my wallet. I figured I'd be able to find someone to go with me, so I sucked it up, made the purchase with the hundred cash, and stuck the tickets in my back pocket. In my side pocket I placed the change -- $60.

The opening band had already started, and she was standing behind me, her arms around my waist, burying her face in my back. It would have made me uncomfortable if it wasn't so damn hot. I began to realize I simply didn't care about her boyfriend. He had been an asshole to me, and since I wasn't even initiating the physical activity, I felt no guilt. By the time The Thrills (who did not live up to their name) hit the stage, she was pressed up against me from behind with her hands in my pockets. She was very handsy throughout the show, and between the music and the closeness and the hands, I was very turned on.

Then the show ended. Lights came up. I stuck my hands in my pockets and found them strangely light. Jessica was dancing back and forth all Juliette Lewis-like and didn't notice my demeanor had changed.

ME: Hey, when you had your hands in my pockets did you knock anything out?
JESSICA: When I took my hands out, I think some paper fell, but it just looked like junk.
ME: It wasn't. It most definitely wasn't junk. It was all really important papers for my new job. I need them. And money. I had like twenties in there. Did you knock it all out?
JESSICA: Maybe! Oh no!

She dropped to her hands and knees and began searching the floor for the documents and the cash, people stepping around her like she was insane.

Which she was.

Panicked, I checked the back pocket. The Femmes tickets -- Gone Daddy Gone.

After a half hour of searching, I went to the box office to see if anyone had turned my stuff in.

CLERK: Oh yeah, in New York City somebody turned in 60 bucks cash and concert tickets.
ME: Seriously?
CLERK: Of course not.

We went out into the night. The two of us standing on a street corner, Jessica sobbing and apologizing. Forms I needed to fill out and bring to my dream job the next day to show how responsible I could be -- vanished. So far, I had blown about $300 I didn't have on a date that wasn't even a date with a girl who had a boyfriend.

And the night was just beginning.

She wouldn't stop crying, so I put my arm around her. I assured her that it wasn't a big deal and that I was OK with it, though it was and I wasn't.

I just wanted to get the night over with. I guided her toward the subway. For you New Yorkers, we were walking from Irving Plaza to the Union Square subway stop, the one in the gazebo. She told me she didn't want to go home, and asked if I would sit in the little park there with her for a bit.

We sat on a bench and struck up some conversation, most of which consisted of her apologizing. On the bench to our left was a teenage couple dry humping. On the bench to our right was a homeless man who smelled like the dumpster at the base of Poo Mountain. Romance was in the air.

We couldn't help but sneak glances at the teenagers, who were rounding second base. Before I had enough time to think better of it, Jessica and I were kissing. It was dark, we were outside...it was nice. Kissing turned to making out. After ten or so minutes, she pulled away.

JESSICA: I'm sorry. We should stop.
ME: Oh. OK, sure.
JESSICA: I really like you.
ME: I like you, too.
JESSICA: No you don't.
ME: Of course I do.
JESSICA: You shouldn't, though.
ME: Why is that?
JESSICA: Never mind.
ME: Because of your boyfriend?
JESSICA: No. I don't care about him.
ME: Why don't you break up with him?
JESSICA: I can't.
ME: Why not?
JESSICA: I love him.
ME: Oh. OK.
JESSICA: I like you too, though.
ME: Look, somehow this is way more serious than I expected, I just wanted to take you to a concert. If you love your boyfriend, stop hanging out with me. It's that simple.
JESSICA: But you like me, right?
ME: Yes?
JESSICA: You shouldn't.
ME: What are you talking about?
JESSICA: If I tell you something, do you promise you won't tell anybody?
ME: Of course.
JESSICA: Promise me. Nobody.
ME: I'll never talk to anyone at Kaplan again, Jessica.
JESSICA: And you promise you won't hate me?
ME: Of course not.
JESSICA: And you won't freak out?
ME: Jessica. What is it?
JESSICA: OK.
ME: Go ahead.

JESSICA: OK. I have hepatitis.

GA-GOO?!?!

I felt an immediate desire to gargle and spit. I knew nothing about hepatitis, but the little I did know involved the words "saliva" and "blood" and "contagious."

JESSICA: I didn't get it from sleeping around or anything. I'm not a slut.
ME: OK.
JESSICA: I used to be a dental assistant, and I didn't use my gloves once and the doctors think that's where I got it.
ME: Uh-huh.
JESSICA: You look freaked out.

Freaked out didn't even begin to describe it. I'd imagine my hair was standing on end at this point. Had I been wearing a bow tie, it would have been spinning out of control.

JESSICA: Are you freaked out?
ME: Well, we just made out, you know?
JESSICA: Yeah.
ME: Isn't hepatitis like highly contagious?
JESSICA: It can be, yeah.
ME: Well, can't you get it from kissing?
JESSICA: Yeah, but that's a different kind, that's not the one I have.
ME: Well, are you sure?
JESSICA: Yes! Jeez. You told me you wouldn't flip out.
ME: Well, if I have hepatitis I am definitely going to flip out. I'm really really going to flip out.
JESSICA: See, this is why I can't leave my boyfriend, no one's ever going to like me with this.
ME: That's not true.
JESSICA: It totally is. You should see your face.
ME: I'm not even worried, I promise.

I have hepatitis I've got to get to a doctor I have hepatitis I've got to get to a doctor I have hepatitis

JESSICA: I should get home.
ME: Good idea.

We went down into the subway station. If you've been to NYC, you know they have standard turnstile entries and they have the giant cage entries that you push through like a revolving door. This was cage-style. I swiped my subway card and yes, more problems arose.

JESSICA: Oh no! I don’t have my Metrocard!
ME: Just buy a $2.00 one!
JESSICA: I don’t have any cash!
ME: I’ll give you two bucks!
JESSICA: No! I can’t take any more money from you! Just go!

I walked through the cage door and at the last second she put her arms around me, piggybacking onto my fare. I suppose this wasn't a huge deal, it was midnight and the subway was deserted. I came out on the other side and looked behind me. Her purse had gotten caught on one of the claws. She kept tugging and pulling at her purse strap. She asked me for help, I walked over to pry it loose.

And two policemen walked around the corner.

COP: You two turnstile jumping?
ME: No. No.
COP: Yeah, we got cameras back there.
ME: Oh.
COP: Get the bag loose and come with us.
ME: There’s no other crime going on in New York City right now?
COP: Get the bag loose and come with us.

There's a little police station inside the subway stop at Union Square. We were escorted there and sat down in a little room. Both cops were really checking out Jessica's body, and I couldn't help but hope that her looks would be of some help here.

COP: Do we need to show you the tape of the incident or do you guys admit to it?
ME: We don't need to see it.
COP: OK, I've got to give you both a ticket.

Jessica stood up, she gave them some cleavage, she was on fire.

JESSICA: No! No, please don't! Please, if you have to give somebody a ticket, give one to me and not him. Please. He didn't tell me it was OK at all, I just snuck through with him. I've caused him enough trouble tonight, I lost all his important papers and his concert tickets and his money and he hates me now! Please just give me the ticket not him! Pretty please, officer!

The cop stared at her for a moment. Gradually, a smile crept across his face. He looked at me.

COP: You two on a date, sir?
ME: Yeah.
COP: You're a lucky man.
ME: Yup.
COP: Beautiful girl who sticks up for you, that’s a wonderful thing.
ME: Definitely.
COP: Look, we're being watched too. If my boss sees me bring you guys in here and not give you a ticket, I'm in the shit. Let me see your licenses, OK?
JESSICA: Look, officer, please --
COP: Cameras are on here. I'm filling these out, but I'm messing up your info on purpose. I'm not checking a fine. You won't have to pay it, OK?
JESSICA: Thank you sooo much, officer.
COP: No problem.
ME: We really appreciate it.

The cop handed the tickets to us, reprimanded us with a smile and a wink, and sent us on our way.

COP: Take care of that girl, buddy!
ME: You know it!

I couldn't believe it. Finally, a bit of luck.

Jessica and I took the subway up to the Port Authority. We were each taking a different bus back to New Jersey. As I walked her to her bus, she opened her ticket. Indeed, the cop had entered all of her information incorrectly, rendering the ticket void. There was no fine checked, and he had even drawn a little smiley face in the corner. Jessica apologized yet again. I told her it was no problem and that I'd get over it, though it was and I wouldn't. She leaned in to kiss me goodnight.

Needless to say, I gave her my cheek. Bitch got hepatitis.

As she boarded her bus, I looked at the clock -- 12:55. If I didn't catch the 1AM bus, I was screwed. The only bus after that was the 2AM, which always came late, and often not at all. I sprinted through the Port Authority, my heart pounding in my ears. I ran downstairs. The clock still read 12:59. I was going to make it!

I pushed the door open and ran outside to see my bus, the 99S, roaring away into the night. For the first time ever, it had been early.

I went back into the Port Authority and slumped to the floor. It's pretty much the filthiest, most miserable building in the world in the daytime, and after dark it's just plain terrifying. And I was stuck there indefinitely. I reached into my pocket and pulled out the ticket the cop had given me.

And every detail, every spelling, every number was totally accurate.

He had given me a $60 fine for "Subway Fare Evasion."

I would later write a letter of appeal to the NYPD. The appeal was denied.  

When a hepatitis scare is the most fun part of your date, it's time to be single for a few months.

The 2AM bus arrived at 3:15.

tags: worst date of all time  work  new york  

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