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Toby Samson, who's participating in Stephen Lewis Foundation’s Dare Campaign, skates at Nathan Phillips Square in downtown Toronto on Dec. 23.Kevin Van Paassen/The Globe and Mail

When Toby Samson moved to Toronto six months ago, she was ready to jump into life in her adopted city.

The 22-year-old just graduated from McGill University in Montreal last year. Born and raised in Vancouver, she considered going back to the West Coast, but says she was ready to try Toronto for a change.

"I'm a very proud Vancouverite," Ms. Samson says. "But I'm so happy with my decision to move here. … I want to stay here for the next few years at the very least and just really get to know the city."

So to complete the transformation from Vancouverite to Torontonian, she says she'll be "daring" herself to do things she's never done before – and she'll be doing them for a good cause.

For $20 per suggestion, people can dare her to do Toronto-centric things, like trying karaoke in Chinatown or chugging a beer in the Distillery District. The money will go to the Stephen Lewis Foundation's Dare Campaign, which raises money to fight AIDS in Africa.

Ms. Samson says that although she works as a local tour guide, sometimes she doesn't have time to try the things she recommends to other people. "There's always those things that you hear about, where you're like, oh, I should do that, but you never really make the time to do it," she says. "So my dare is all about making the time … and really taking advantage of the fact that I live in such a great place."

In January, she hopes to kick things off with a scavenger hunt, where she'll have a beer in the Distillery District and skate in Nathan Phillips Square. Then she'll chronicle these adventures on her blog. The one dare that will really be a challenge? Ms. Samson has never learned to skate.

"I'm sure the pictures will be of me falling every time I stand up on a pair of skates, I'll get a lot of my friends' support for doing that," she says, laughing.

Ms. Samson is just one of the 150 people who are part of the Dare campaign, all trying to conquer their fears or do something challenging, and help a good cause in the process. So far, the campaign has raised about $1.3-million for projects like the City of Joy, a safe refuge for women in the Democratic Republic of the Congo who have survived sexual violence.

Several Canadian icons have been part of the effort. In October, 2009, Toronto rapper K-Os went back to the first job he ever had, working in the toy department of The Bay.

CBC host George Stroumboulopoulos took on a dare that involved learning figure skating from Kurt Browning. That may sound intimidating enough, but after lacing up his skates, Mr. Stroumboulopoulos also put on a Leafs jersey, despite being a diehard Habs fan.

This year, Murray Foster of the band Great Big Sea will also be added to the Dare Campaign's roster. In January, he'll be writing and recording one song a day, and, if fans want to listen in, they can donate to his dare.

This year, other dares include embarking on the Tour d'Afrique, biking over 12,000 kilometres from Cairo, Egypt to Cape Town, South Africa. Another one involves climbing Mount Kilimanjaro.

But Keely Wallace, a spokesperson for the campaign, says dares don't have to be nearly as drastic. "The great thing about the campaign is that it's malleable," she says. "If you want to do something as simple as giving up coffee for the month of January, that can be your dare."

None of Ms. Samson's dares involve giving up coffee, but there is one thing she'll have to give up if she wants to become a true Torontonian – her love for the Vancouver Canucks.

"I genuinely had tears dripping down my face when they lost the Stanley Cup," she says. "Realistically, I'm never going to like the Leafs over the Canucks, but I'm going to get more into them. … So I think I'm going to have to get myself a jersey and really commit."

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