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Dempsey says banner towing, which can cost between $250 and $550 a pop, not including the price of any custom-made signage, has its share of unique dangers and dilemmas. "A lot of people consider this type of flying to be high-risk. This and crop dusting. Fortunately, we've been flying without a fatality or an injury since we started. Most of the danger is in the pickup. On real windy days, if you're coming in to pick up you're bouncing all around. You're only 12 feet off the ground, and those poles are six feet off the ground, so you have to really watch that you don't get pushed down. That can happen. Sometimes traffic can also be a problem. I've flown the Boston Marathon and some of the NASCAR races and we've had 10 to 13 airplanes flying around at one time, and that is crazy."
Even though it's only 5 percent of his total business, Dempsey says he gets the most enjoyment out of flying personal, as opposed to corporate, ads. "The personal ads are more fun to fly because they have more personality. You see the people waving to you. Sometimes, if it's a 'Marry Me' on a secluded beach where there are only two people, you can see them hug and kiss. It's cool stuff."
Earlier, during the baseball season, Scott Nestlebush hired Dempsey to fly a "Jean, will you marry me? Love, Scott" banner over Cam den Yards during a Baltimore-Seattle game. "People in the sections nearby us stood and cheered when the banner came over the stadium right before the start of the bottom of the seventh. Then the rest of the Camden crowd started to understand what was happening and they started cheering as well," says Nestlebush.
"In fact, the Mariners' pitcher actually stepped off the rubber because the crowd was getting so loud and the players were glancing into the stands to see what was happening. Jean's eyes got real big when she first saw it, but I think it took a moment for it to really register. When she read it the second time, she started jumping up and down ecstatically. Of course, all my friends who have yet to propose are irate because the bar has been raised and now their girlfriends expect something equally cool."