The plans for my proposal actually started a few weeks after we started
dating. Allison and I were at my brother’s house where he was showing us
pictures of a waterfall in El Salvador. Allison mentioned that she had never
been or seen a waterfall. At this moment, I knew if I was going to propose to
her, that it would have to be infront of a waterfall, and it should be
After many long months of planning, I came up with a surprise
trip to Toronto. The idea was to get as close to Niagara Falls, without her
suspecting it, keeping it surprise. I worked with my family, friends, and
co-workers to make this dream engagement a reality.
Working with the Marketing Director at my law firm, I had her make a faux e-mail to the firm, stating that the Red Sox are offering us "Away Game Packages" compliments of the Boston
Red Sox for suite owners. I, of course, won the package to Toronto to see the
Red Sox play the Blue Jays. I planned the whole weekend around her school
vacation calendar, to make sure that she wouldn’t say no to the trip.
Everything went as planned, and we had a fabulous short "company paid"
vacation to Toronto. Allison was under the assumption that we were flying
home Saturday afternoon. While driving to airport, Allison wanted to make
sure that we stopped at a Duty Free shop before crossing the border back into
the USA. What she didn’t know is that I picked a restaurant, which was
directly below the Duty Free Shop at Niagara Falls.
I spent many hours on the phone with the owner finalizing the plan. I hired a cartoonist to draw a
caricature of us sitting on the porch of this restaurant, “The Secret
Garden” with me proposing in the picture. After many phone calls, e-mails
of pictures of us, and proofs. CAROLINES-CARICATURES had a wonderful finished
During lunch, Caroline and her friend, who are real native Niagara Falls locals, played the role incredibly! Allison loves talking to local artists. Caroline introduced herself as a local artist; and
asked if we would mind her drawing us. We both agreed, and she then presented
us with a quick caricature of us. Caroline continued to speak to us. She
then finally asked if we would be interested in seeing a piece that she was
working on for a wedding gift with color. She then handed me the picture and
I then passed it to Allison, got down on one knee and asked her to Marry Me.
I then placed my custom platinum 6-prong Tiffany style ring on her finger.
She was beyond shocked; the biggest surprise to her was that we were actually
flying out the next night, and she could enjoy Niagara including a honeymoon
suite overlooking the falls.
All you art collectors out there. Here is a chance to get a Giclee copy of some of Ian M Sherwin work. Ian is planning on doing a whole series of Marblehead, Massachusetts paintings. His work is amazing.