100 Bad Dates: #9

Date #9 popped my cherry. Not because I was in love with him, but because I was dying to get it over with. It seemed like so much pressure, the whole deciding who to do it with and when. And with so much build up, how could it not be a let down?

January 18, 2010; 12:00 PM • by The Checkout Girl

Date #9 popped my cherry. Not because I was in love with him, but because I was dying to get it over with. It seemed like so much pressure, the whole deciding who to do it with and when. And with so much build up, figuring out how to make it romantic and perfect like it is in the movies, how could it not be a let down?

Anyway, that shit was for silly girls, and I was an independent woman. I decided to go out and find someone who was just inebriated and libidinous enough not to notice what I was sure was going to be a lot of wincing and a red sea (thanks, Judy Blume) and romance him for the amount of time it took to make it happen.

Date #9 was a military man. I convinced my best friend, who had already lost her virginity to a neighbor when we were still in middle school (and many, many times since) and whose dad was a retired officer, to use her dependent ID to get us on base to where the boys were chock full of hormones. It took a bit of swaying because she had a serious boyfriend and had her own plan to get pregnant so he would marry her.

“Ok, but we’re not staying long. I think I might be ovulating and I’m going to call Steve to meet me at home so we can do it,” she said.

Yep, we still said “do it” which means we were too young to actually do it.

We got to the Enlisted Club and I saw Date #9 right away. How could I not? At 6’8” he was the tallest guy in the place. That dark, smoky room was full of hot boys and slutty girls, but my eyes kept going back to him. Eventually, he looked my way and smiled. It wasn’t long before he headed over.

“What are you drinking?” he asked, leaning closer than someone sober would.

“What are YOU drinking?” I countered.

“Ah, the lady takes care of herself, does she?” he said with a wink in his voice.

Date #9 and I spent the next hour getting to know each other a little by shouting over the music. I am slightly hard of hearing and so mostly I nodded while he yelled. In fact, he said his name twice, but I just couldn’t get it. I realize now that I should have had him write it down or something. Finally, I decided to just nod at that, too. The bar was closing and my friend was totally bored and hyper-aware that ovulation is a limited time offer (and only once a month at that), so we headed outside.

“Where are we going?” he asked.

“I’M going home,” she snarked, “YOU guys can go wherever.”

“Well,” he turned to me, “wanna hang out some more?”

Um, yeah, that was the plan.

We went for a drive in Date #9’s car and ended up parked, looking out over the bay. He asked if it was ok to kiss me which struck me as sweet. I actually wanted him to, which was NOT part of the plan. He did, and things got real hot real fast. There were hands starting at the top and moving down. First over, then under. I figured out that the actual deflowering couldn’t possibly take place in the car, considering his height. I stopped him.

“Do you want to go to a motel?” he asked, the picture of class. I was willing, which made me just as refined.

We ended up at a nearby establishment that, luckily, had left the light on for us. Once we got in the room, I jumped on the bed, totally ready to get this thing over with. He joined me and we kissed again.

It didn’t take long before we were at the point where it was fish or cut bait, and I decided to fish. It was over in a flash. Very little wincing, no red sea that I could, well, see. In fact, not much of anything at all. That was it? We snuggled a bit and I felt a bond with him that I hadn’t expected. DEFINITELY not the plan. Finally, he broke the silence.

“I should take you home. It’s late.”

I felt a pang of something.

Date #9 drove me home, and I gave him my number, simultaneously hoping he both would and wouldn’t call. I didn’t know if I could face him again, being that I slutted it up so hard just hours after meeting him. At the same time, I suddenly felt dirty and thought that if we went out again it might make me less of a whore. He didn’t call and I learned a hard lesson: even independent women have feelings and things don’t always go according to plan.

The Checkout Girl, originally from Southern California, is currently bringing sexy back to Richmond. She is enjoying seemingly limitless amounts of sweet tea, middle-aged women in tennis skirts, and humidity. 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.

January 18, 2010 12:00 PM 4