100 Bad Dates: #50

Date #50 and I met when he was in town visiting a friend. We kept in touch after he went back to his hometown in the Midwest. When he talked of coming back into town to hang out, we settled on New Year’s Eve for our next date.

December 28, 2009; 12:00 PM • by The Checkout Girl

Date #50 was a sexy centerfold just waiting to happen. We met in October of 1999 when he was visiting a friend in my city from his rural hometown in the Midwest. Mutual friends introduced us, thinking we would hit it off. They were right. I liked his Country Mouse ways and he was dazzled by my City Mouse savvy.

Date #50 and I hung out a couple of times while he was around and kept in touch when he went back to driving a mail Jeep in his two-horse town. We emailed, racked up quite a phone bill, and became generally fond of each other.

When he talked of coming back into town, we settled on New Year’s Eve for our next date. That was huge because the mood world-over was all Y2K-y and, you know, we could possibly die together when all of the world’s computers got confused and thought it was the year 1900 and suddenly hadn’t been invented yet, I guess? Anyway, for those of you who don’t remember, a NYE 2000 date was a big deal.

Date #50 arrived on New Year’s Eve Eve, but I didn’t see him until I went to pick him up for our date. My best friend was having a party (she had reserved the right to host the Y2K soiree in, like, 1995) and, even though she lived about an hour away, I kept my young adult promise to attend. He pretty much looked the same, save for one obvious change that had taken place.

He had breasts.

Not like moobs (man boobs, for those not well-versed horrifyingly inappropriate slang), but like big, bodacious tots. We embraced, and it was like hugging a Hooters girl. If you’ve never had the pleasure, it’s not altogether bad.

We headed to the party and had plenty of time to catch up while making the trip. He mentioned he had gained some weight, and I politely said that I hadn’t really noticed. He explained that he was on a medication that caused him to put on thirty pounds (They weigh fifteen pounds apiece? Awesome!). Honestly, I was fascinated by his double D’s and kind of hoped I would get a chance to see them up close.

We got to the party (which was full of people who had nothing in common except for the fact that they had met my bestie sometime in the past five years) and I sat next to him as we drank and made small talk with boring people. After a few more shots of slut juice (in this case, tequila — it gets me every time.), I moved from the couch to his lap. After another shot, I reached up to cop a feel. He didn’t seem at all uncomfortable, and I was like, “Hey look how my date is the best of both worlds with a penis and an ample bosom and oh my gosh I hope we don’t all suffer nuclear annihilation due to computer malfunction before I get my hands on both!”

Midnight came and went without a bang. I wouldn’t say we were disappointed to live or anything, but not even ONE stray missile or plane falling from the sky? Gyp! After drinking far too much to drive home, the bestie offered her guest room.

Even though we were too tipsy to celebrate the millennium, carnally, we DID get peeled down to undergarments to sleep it off. That’s when I saw them. It was like half of a Playboy centerfold up in that bitch! We snuggled up, and I rested my hand on one and passed out.

I woke up sweaty with my mouth tasting of the bottom of a shoe. Date #50 was sitting next to me on the bed, fully dressed.

“I don’t think this is going to work out,” he said, “I’m sorry.”

I asked him what was going on and if he was ok. He said he just didn’t think we were right for each other. I was pretty sad but, let’s face it, I hardly knew the guy. We rode back to his friend’s house with only the car radio to break the silence. When we got there, he apologized again. I hugged him and told him to take care.

I’ll never know what happened that night. Maybe I got all randy with his juicy melons and don’t remember. Maybe I farted in my sleep. Maybe it was my terrible snoring problem, which is the stuff of legends. Still, nothing changes the fact that I was dumped by Pam Anderson’s breasts on the first day of the new millennium. It didn’t give me much hope for the next 1000 years, but does give me plenty of time to plan a kickin’ Y3K party. Dibs.

The Checkout Girl is a recent transplant to Richmond, from San Diego. She is obsessed with celebrity gossip, good yarn, garish lipstick, and memoirs. She’d like to learn to play the ukulele, cook more than microwave meals, and master the French language. She writes her work and life adventures at thecheckoutgirl.net, as well as the advice column Ask The Checkout Girl for Belle Magazine. After more than 100 bad dates, she’s found a pretty good guy.

December 28, 2009 12:00 PM 3