I remember the morning Jenny called me up, all excited about a new idea she was formulating in that whirlwind mind of hers. “What do you think of a ‘Chicago’s Most Eligible Bachelor and Bachelorette’ contest?”
“I LOVE it,” I told her. The details of it all hadn’t been fully decided yet at that point, but I felt super-excited for the potential it carried for all the people that would enter. What a unique way to meet someone! It sounded cooler than all the other matchmaking methods we’ve all heard of.
It was the first time I ever saw one of Jenny’s ideas blossom from concept to fruition, and it was of course one of the funnest things I’ve had the chance to be part of.
“I’m curious,” I also told Jenny that morning. “What made you think of this?”
“Well, doing what I do, a lot of men and women ask me if I ever work with single people I could possibly set them up with,” she said. “I just thought that this way, we could have some fun playing matchmaker.”
And the nominees are . . .
Usually, when it comes to “putting ourselves out there,” a lot of us can be really shy. Fortunately, Jenny had provided plenty of motivation for the ladies to win: Whichever female contestant would win the title of Chicago’s Most Eligible Bachelorette would win a complimentary “glamifying” makeover by Jenny’s skilled makeup artists and a swag bag containing goodies from local businesses. (It was almost enough to declare myself single and compete for the title myself!)
There were chances for three matched dates to occur after the Dating Game to take place on Sunday, March 25. If any of the female contestants matched with their corresponding male contestant (they would be divided by a wall during an hour-long interview), the couple would then win a dinner date on the house at the participating restaurant of their choice. (And a Great thanks goes to Maggiano's of Naperville --Francesca's --RoseBud of Naperville for providing such generous Dinners to our Winners that evening!)
In any case, we were considering the idea of inviting all contestants to a mixer to meet everyone who’d entered, so everyone would really have the chance to meet someone special. (We’re still playing around with the idea, so stay tuned.)
For a while, ladies all around Chicago were pouring in for a chance to nab the title. I was surprised to learn that it was the gentlemen, who are usually so vocal and enthusiastic about Jenny’s work (for obvious reasons), that were a little hesitant to enter.
Then Jenny announced that she would be taking nominees (with their permission, of course). I immediately thought of my boyfriend’s good friend Wiktor, who is hilarious and has always been a total gentleman, never missing an opportunity to hold doors open or walk you to your car. I sent Jenny a picture of him in a tux and a brief explanation describing why I thought he deserved to win, and when she called him to confirm his entry, he must have really won her over because the excitement was obvious to me the next time I talked to them both!
“Jenny is awesome,” Wiktor said as soon as I answered his phone call. To thank me, he offered to buy me dinner. And, as it turned out, one of his friends had also been entered, and they’d placed a private bet between them! If one of them should win and hit it off with his date, the other would pay for their second date. (Wiktor is a competitive guy.)
“Jenny is awesome,” Wiktor said as soon as I answered his phone call. To thank me, he offered to buy me dinner. And, as it turned out, one of his friends had also been entered, and they’d placed a private bet between them! If one of them should win and hit it off with his date, the other would pay for their second date. (Wiktor is a competitive guy.)
I found that it was pretty hit-or-miss when it came to finding willing nominees for the contest — some people were really open to the idea and enthusiastic to try something new, but others were a bit too nervous.
It really depended on a person’s attitude towards how they wanted to look for love. The best contestants were always the ones who were game enough to see what it could yield for them — because really, you never know. Plus, the nature of the Dating Game was such that emphasis was placed mostly on inner qualities, with interview questions for the finalists prepared specially to showcase their interests and personalities.
Tally up the votes...
In fact, that was also the whole structure of the contest: For a week, all contestants’ photos and “reasons” for entering were displayed on the blog for a public vote. As an important aside for all future participants, remember to read Jenny’s contest rules! I felt bad for some contestants who received tons of votes by anonymous people; whose votes wouldn’t qualify.
After the week whizzed by, Jenny counted the qualifying votes and announced our first lucky set of finalists: Heather and Paul.
Then, in a flurry of four and a half hours, Jenny and her awesome assistant Amber interviewed each of the remaining contestants to determine which might hit it off best based on their answers.
The Dating Game
On Sunday, the environment of the studio, which is usually so open to exploration, was buzzing with excitement for what was to come. Ladies and gents sat in separately with a wall in the middle, with an audience on couches behind them.
Jenny stood in the center with an extensive list of questions. These questions were thorough and important, covering a scope from “What’s your favorite kind of restaurant?” to “Would you like to have kids one day, and if so, how many?”
And the winner is . . .
As the hour went by, all the contestants, numbered 1-3, answered each question in turn with a notepad in hand, scribbling notes down so they could determine who they were most interested in going on a date with. If there was a match (e.g., female contestant 3 picked male contestant 1 and vice-versa), those two would go on a date.
I know you’re wondering now, what would happen if no one matched?
Well, we didn’t want to think about that because we wanted to think we did such a great job of matching that it was impossible . . . but alas, as fate would have it, that would be the one little bump in the road!
Since Jenny loves to give prizes away, and she had worked so hard on this contest, she decided to award each couple a dinner date — after a lot of consideration, it was best to match our finalists with the contestant Jenny and Amber had originally thought of pairing:
As soon as the contestants were revealed to each other, sparks already began to fly.
The game had been a hit! So many people loved it and have asked Jenny to hold another one that it seems like a total shame to let this round be the first and only one . . . especially if you missed your chance to enter! So the gears are turning in Jenny’s head for future, updated versions of the contest and Dating Game. I’ll be sure to keep you posted.
Curious to see how the dates went? Check back on Wednesday for an exclusive interview of one of the winning couples . . .
