As this is one of the most frequent questions I get asked (that hasn’t changed), I thought I would repost this blog. Originally published January 3rd, 2015. As I have yet to win a car, my answers are still the same.

Robbie on Facebook asked me: Curious as to what your biggest win has been so far?

Since it’s a question I frequently get asked, and it has three parts to the answer, I thought my response was best suited to a blog post.

The answer really lies in what one defines as the biggest. The most valuable was a trip to the 2010 Winter Olympics. The best win was a trip to the Harry Potter set in 2005. The priceless win was meeting Sting.

Let me go into a wee bit more detail for each of my answers.

2010 Winter Olympics

I won this trip while I was still married. It was sponsored by Wonder Bread. They had an online contest where you could enter one person per household per day. After signing in you played a little game to instantly win mittens. I would alternate entering me and my spouse. We never won mittens but his name was selected as one of three grand prize winner. (I consider it ‘my’ win as I did all the entering.) This trip falls into the ‘biggest’ category as the ARV was over $20,000.

You can read about the entire trip on my original blog post: 2010 Vancouver Winter Olympics


London UK

I also won this trip while I was still married. It was sponsored by The National Post. It was a short contest as it only ran for five days. I missed the first day. For the following four days, I entered myself and my then-husband. Again, it was his name that was selected as the grand prize winner. This trip falls into the ‘best’ category as it was surreal.

You can read about the entire trip in my original newsletter article: Whirlwind Weekend



I do not remember much about entering this contest. I don’t even remember when I won it. I only remember the prize as it’s my favorite. We won an opportunity to listen to Marilyn Dennis interview Sting at the Bravo studios downtown Toronto. We were wondering why it was taking so long to seat the 50 winners and their guests. Then we found out. Sting personally greeted each attendee, thanked us for supporting his music, and took a group photo. I was lucky enough to be beside him and put my arm around his waist. (He smelled really good too!) This trip falls into the ‘priceless’ category as you can’t buy an experience or memory like that.

The only thing I am sure of is I won it before 2005 as I did not write or blog about it.

C&C with STING

All that said, those are my answers today. I could win a prize tomorrow that could turn this list upside down.

What was your biggest, best, or priceless prize to date?