Lemondrop

In theory, participating in a live dating auction to benefit the Dana Farber Cancer Institute is a wonderful thing to do. You raise money for an incredibly worthy cause while letting a charitably-minded set of men with disposable income know that you're available, and brave.

In reality, participating in a live dating auction is among the most terrifying things you can do, voluntarily.

When my friend Julie emailed to inquire about my willingness to participate in her annual Date My Friends auction -- a fund-raiser for her Boston Marathon run -- I read three things: 1) Dana Farber Cancer Institute, 2) Boston Marathon, and 3) date.

It's not that I didn't register the word "auction"; it's just that standing alone on a stage while an MC begged hundreds of Manhattan 20-somethings to buy me didn't instantly flash through my mind. Maybe I thought it would be a silent auction? Maybe I thought all the "contestants" would stand together onstage as people placed money in our corresponding jars? I don't know.

What I do know is that you can't back out of a charity dating auction once your picture's been included on a flier that's been distributed across Facebook.

Luckily the power of "Come on, it's for charity!" had as strong an effect on the male friends I begged to fill the audience on my behalf as it did on my willingness to participate. The trick is to place "I need you to come bid on me in a co-ed charity dating auction" directly in the subject line of the email.

I arrived at the auction location -- a Manhattan bar -- to a teeming crowd of young professionals holding identical pieces of paper and staring at everyone who walked in with an "Is that person for sale?" look. Immediate thoughts: Who else is getting auctioned off? Are their outfits cuter than mine? Where am I going to have to stand? Is where I'm going to have to stand going to work with my outfit?

It is weird to have a hundred or so people holding your picture and trying to match it with your face. It's weirder still when you overhear them saying, "That girl seems pretty good." But it is weirdest when one of them comes up to you and says, "Jessie? Good. I'm going to win you."

At this point, several of my friends had arrived and slipped nicely into Jess-prep mode. "I'm on vodka sodas," Sara said as she went to the bar to refresh my liquid courage.

"We've been walking around looking at all the other girl options, and your dress is the cutest," Lillian assured me.

"So what do you want me to bid on you?" asked Brian.

"I just want to go for $50," I told him, "and I'll totally pay you back."

"It's for a good cause," he replied. "I'm willing to split it."

Having given obsessive thought to the intricacies of the dating auction, I'd decided auction order was of primary importance. You absolutely do not want to go first. You probably don't want to go last. But even more importantly, you cannot go after someone incredibly good-looking or with an obvious fan base in the audience. Since this was a co-ed dating auction, I decided it was most advantageous to be person three: One girl, one guy, then me. Was there a pre-determined order for the evening? Yes. Did I beg them to change it so I could go third? I did, and I am not ashamed.

After an hour of milling around the bar as clusters of guys awkwardly milled around me, I was raring to go. I'm not the best judge of audience size, but I'd say about 50,000 people had gathered at this point. I briefly entertained a fantasy where the fire department arrived to shut the event down for overcrowding, but the MC started the auction before I could finish dialing their number.

GULP.

Girl One took the stage. She was blonde, long-haired and adorable in an Anne of Green Gables–takes-Manhattan sort of way, not to mention wearing a very short black dress belted at the waist. In other words -- the opposite of the type of girl you want to go after.

After an excruciating five to eight minutes of the MC begging for bids as Girl One smiled that uncanny get-me-off-this-goddamn-stage smile, the biding was closed. Girl One went for an incredibly respectable $80, $30 more than my goal price. I shot Brian a we're-going-to-80 look; he rogered that.

"How are you feeling?" my friend Lillian asked as Girl One came down off the stage.

"Not good," I said through my mini drink straw.

See, I'd been so focused on the please-God-let-someone-bid-on-me fears that I'd forgotten to focus on the OMG-what-happens-if-a-random-guy-wins-me scenario. A random guy won Girl One, and their awkward exchange (Guy: "Hi, I'm Andy." Girl: "Hi, Andy. Thanks for, um, paying 80 bucks for me?") was the last thing I heard before Guy Two took the stage.

I'm told that Guy Two went for about $125, but I was too busy practicing standing, holding a drink and looking amazing to pay much attention. Or wonder why men went for more than perfectly cute women. And what that meant. Because then it was my turn.

DOUBLE GULP.

The "stage" was actually a flight of stairs facing the crowd, so naturally I tripped on them upon taking my position. You know how when you're performing on stage the audience is impossible to see because their section is all blacked out by the lights? This wasn't like that. I could see every single set of 50,000 eyes staring up at me as the MC said, "OK, now we have Jessie, and we're going to start the bidding for this fiiiiiine lady at 50 bucks!"

I'm told I leaned over to him and said, "Nooo!! TOO HIGH!!!" but I'm afraid much of what happened in my five to eight minutes on that stage is a blur.

A five-man bidding war broke out on my behalf, driving my sale price up to $220 in three minutes. I knew three of the bidders -- two friends and a co-worker -- but two other guys were in-it-to-win-it, and I had never seen them before in my life.

I sold for $240 to a good friend / co-worker with a competitive streak and a personal commitment to cancer research. The crowd cheered, the losing bidders shook their heads, and the MC said, "Well, hamming it up was obviously a good strategy."

I decided to take that as a compliment.

I kindly thanked the mystery bidders for their interest in purchasing me and awkwardly introduced myself (Me: "Hi, I'm Jessie." Guy: "Yeah, I know.") Word to the guys -- being the almost-winner in a dating auction is a genius way to meet girls. I didn't hit it off with either of my would-be suitors, but had there been more chemistry the this-guy-just-tried-to-buy-me factor would have really worked in their favor.

In the end, it was a success, for a great cause, with far less pain than I'd imagined. That said, I could definitely have done without the "I thought you looked like the girl from 'Glee' and I totally want to bang her" confession from "Dave," who was apparently willing to pay $175 to try it with me.


Jessie Rosen writes the blog 20-Nothings.com, an account of getting by from 2-0 to 3-0. After this feat, she'll never fear a blind date again.