It was a sultry late-summer evening when I spotted her standing across the crowded ballroom.
Screwing up my courage, my heart hammering in my chest like a heavy- metal drummer, my hands clammy with sweat, I staggered nervously towards her.
Within moments, I was next to her and, looking deep into her eyes, blurted out a question I'd been dying to ask since the moment I'd walked into the ornate room on the seventh floor of the Fort Garry Hotel.
"Would you like to sleep with me?" I croaked, before politely adding: "Again?"
There was a delicate pause as she pondered how to respond to this bold proposition. After an eternity, she looked at me, a gentle smile betraying a mix of amusement and pity.
"Yes, of course!" city councillor Jenny Gerbasi chirped with glee. "If it's for a good cause."
And on Thursday, Sept. 26, when the Fort Rouge councillor and I bunk down under the stars in a small courtyard near the corner of Portage and Main for the second straight year, it will be for a great cause.
It's going to be an intimate evening -- just Jenny and myself and about 98 other community and business leaders and media personalities hunkering down in our sleeping bags on small patches of grass in front of 201 Portage Ave.
For the record, it's all part of the Downtown Winnipeg Biz's third annual CEO Sleepout, which aims to raise $150,000 to help get homeless Winnipeggers off the streets and into jobs and decent housing.
The money we raise -- and online pledges have so far topped $85,000 -- will go to the BIZ's Change for the Better campaign, which supports employment programs for the homeless, such as Siloam Mission's Mission Off the Streets Team.
As Jenny noted during an event last week to unveil this year's 100 participants -- double the roughly 50 CEOs who slept out last year -- it's not about pretending to be homeless for a night.
It's about shining a spotlight on, and raising some cash for, a crucial issue by giving some high-profile Winnipeggers a small taste of what the city's most vulnerable citizens experience on a daily basis.
"Some people see it as an 'Us vs. Them' issue, but homelessness is something that could happen to anyone and it's something we as a community have an obligation to deal with," she said. "It's about doing what we can do, and getting a bunch of high-profile people to focus on the issue. And that's a good thing."
One of those high-profile people is Brian Scharfstein, the community-minded president of Canadian Footwear and chairman of the Winnipeg Chamber of Commerce.
This will be the third year Scharfstein has joined the sleepout, and while he describes it as "the greatest opportunity to give back to our city," he acknowledges camping in a concrete courtyard is "a painful experience."
"You never really relax, you never get comfortable, and it takes you days to recover. I would not want to have that feeling every night," he said.
Stefano Grande, executive director of the Downtown BIZ, told this year's bumper crop of sleepout CEOs ending homelessness is a part of his organization's mandate.
"We believe we need to be on the front lines every day helping people," he said.
That's why the BIZ has already hired one outreach worker and is in the process of hiring another. Eventually, it hopes to have as many as eight patrolling downtown streets.
"They'll be out on the street every day bumping into people saying, 'What can we do to help you?' and making connections with housing and employment and addiction counselling, doctors and social workers," Grande said.
He believes there's a growing realization the business community has to be part of the solution. "We're in an era where the corporate community doesn't operate in a vacuum," he said. "There's a social consciousness expected."
Which reminds me: If I'm going to sleep out on the cold, hard streets again, it would make me feel warm and fuzzy all over if you coughed up a little cash for the cause.
So, please, drop whatever you are doing -- even if it's a hot cup of coffee -- visit www.changeforthebetter.org and click the "Donate Now" button under my photo. Or Jenny's.
Because, like the song says, if, on some enchanted evening, you should see a stranger across a crowded room, never let them go... without first giving them a big fat donation.