On Wednesdays, Amanda Chatel will be sharing stories about her strange, fascinating and sometimes wonderful dating life. If it makes you want to date, check out TheGloss dating page.

When my friend Anne decided she wanted to give online dating a try, she also felt I should as well. I did not agree with her, but this didn’t stop her from creating a profile for me.

Anne, being the complete opposite of me, made my profile just like hers, but to use her words “edgier.” I think “edgier” in her mind was meant to represent the difference between the two of us. She prided herself on having this Jennifer Lopez body and did everything in her power to even look just like her physically. I, on the other hand, had tattoos and I had seen Nine Inch Nails in concert — in high school well over 10 years ago. So considering Anne’s affinity for commercial radio, her favorite store being Express and having never tasted a cheese even remotely more interesting than cheddar, I truly was in her mind “edgy.” We had been friends since 4th grade and somewhere along the line we had changed drastically in our personalities and preferences. I was “edgy” (although I’m really not) and she was something out of crowd of TRL fans on MTV — a show I don’t even know still exists.

Anne updated my profile often — which I only saw once strictly so I could roll my eyes — and sort of marketed us as two friends looking for two male friends for a double date. When she finally heard back from two guys who seemed “normal, sweet and not axe-murderers,” she set up a date for us during a weekend I’d be in Boston visiting her. Our weekend, I thought, would be free of drama and mostly involve her perfectly made martinis (she had been a bartender in college) and movie marathons, but when I met her at South Station she shrieked with excitement when she explained: “They’re MIT grad students! Not only are they smart, but I’m sure they’re going to make so much money someday!” Unlike Anne, I wasn’t concerned with marrying someone with the potential to make the big bucks; I was more concerned with bedding a lead singer of an indie rock band.

It took me all of five minutes to get ready for the date. From the couch, I watched Anne apply and re-apply her make-up, curl her hair and desperately try to discern between which shimmery lipstick was most appropriate. I should point out that this was just a few months ago and from what I’ve gathered about life, shimmery lipstick went out in oh, 2001 or so — and that’s being generous.

When all was said and done, Anne looked like she’d been plucked out of a Victoria’s Secret catalog; the back to be exact, where those clothes that I don’t even know who would ever wear muck up the pages with sweaters and jeans that would make most people cringe.

I was in head-to-toe black and Anne frowned at my ensemble. “You couldn’t even try?” she asked.

“For the last time, my soulmate is drunk somewhere in a gutter at the moment, so I’m not really giving a fuck at the moment,” I explained. She reached for her new Kate Spade bag, I picked up my canvas bag that I had gotten at the Strand after dropping too much cash on Franzen and Eugenides novels just the week before, and we made our way to the bar where we were supposed to meet these “MIT grad students.”

For close to 30 minutes we waited. As each pair of relatively attractive men walked through the door, Anne jumped up with excitement to see if they would see her red scarf — that was what they were supposed to be noticing. But nothing each time. As we began to figure that we had been stood up, much my relief and much to Anne’s utter disappointment that I feared I’d have to hold her back from jumping into the Charles River on the way home, she got a tap on the shoulder.

“Anne?” asked a lanky guy with thick glasses that sat crookedly on his nose who wore a sweater that I’m quite certain not even my blind great-grandmother would wear. “It’s me. John.” Underneath the bar, I felt Anne give my leg a tight squeeze. She was silent and motionless otherwise.

“Mandy?” asked the other one who was straight out of the 1980’s movie Revenge of the Nerds with his tucked in t-shirt and high-waited slacks (yes, slacks.) “I’m Twain.”

“Twain?” I asked. “As in Mark?”

“Yeah! Just like that!” responded this Twain character with glee as if he were shocked I could put two and two together.

They sat down and joined us for a drink. Being civil, I did most of the talking while Anne sat silently and ordered shot after shot while John proceeded to put, what I’m assuming were “moves,” on her. When Twain spoke bits of froth accumulated at the corners of his mouth, and when John tried to make a joke it was something so far over both our heads that only Twain understood and laughed. They were awkward in their movements, socially inept in their conversation skills and explained that they didn’t drink — which had already become obvious as they consumed tea, while Anne drowned her disappointment in endless shots (that eventually became free once she unbuttoned her shirt a little more) and I sipped my Guinness slowly.

It was when John and Twain suggested we go to a “hot club for some dancing,” that Anne raced to the bathroom, missed the toilet and threw up on the floor instead. As I stood over her, with her hair pulled back from her face, I asked her if she had learned a lesson. “Yes,” she said, “No matter how interesting someone seems online, if they don’t have a photo up, it’s for a reason.”

“They didn’t have a photo up and that wasn’t a red flag for you?”

“I just want to be in love,” she sobbed. As she continued to throw-up the seven or eight shots she had consumed, I headed to the bar and explained that she and I were going to go home.

“But you seem all right,” said Twain, “You should come home with me. I have new sheets.” As he said this, he put his hand on my thigh, far too close to my crotch, and flirtatiously looked over the rim of his Chester-the-Molester glasses. Could the two of them possibly be anymore stereotypical? Where the hell was Val Kilmer from Real Genius when you needed him?

“No thank you,” I said. I paid our tab and let the MIT kids take care of their tea bill. I carried Anne’s dead-weight drunken body home almost 15 blocks, as cabs in Boston just aren’t as prevalent as they are in NYC while she cried the whole way about love being a joke and being duped by John and his promises. I didn’t ask what promises she meant, but she did promise herself that night to always get a photo before indulging in any online dates again. Since then, she’s had better luck.

I should add, however, that my grandfather went to MIT and he was a pretty crazy, drunken, womanizer, so I’m well aware that John and Twain don’t represent every student there. But I do know that if someone is studying something I can’t even pronounce, I’ll pass. Those people aren’t usually lead singers in indie rock bands who have a habit of being drunk in a gutter somewhere in Brooklyn anyway. And like I said, those are the real “winners” for which I’m always on the look out.

Not all nerds are like Poindexter, some are really hot and cooler than most people. But you won’t know that until you check out TheGloss dating page.