Road-trip documentary speaks to singles at Beloit film fest

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Ann Fiore
Wednesday, February 12, 2014

Bob Murray has some Valentine's Day advice for you lonely singles out there.

First, get out of your comfort zone.

Second, change your attitude.

“Everyone I met was unhappy with their situation,” said Murray, a Milwaukee banker who dated eight single women on a cross-country trip he took while making the comedy/documentary “Date America.”

“You can run from one city to the next, but it's probably not the city” that's the problem, he said. “It's yourself.”

“Date America” is screening at the Beloit International Film Festival this weekend—one of several films in BIFF's new “Wisconsin-Illinois Showdown.” The showdown aims to spotlight regional filmmakers and locations. Audiences can vote for their favorite films, and awards will be given out next weekend.

Murray was in a dating rut when he hatched the plan for “Date America.”

Thirty-four years old and still single, he decided it would be cool to take a cab from Milwaukee to Los Angeles, dating women in different cities on the way. The experience would make great video, he figured.

Easier said than done. Murray had to hire a camera crew and set up dates in advance. He got on a few dating websites—he had the most luck with Okcupid.com—and emailed 50 to 100 women in different cities. Of those, one or two in each city agreed to a date with a camera crew.

Murray said he might have gotten cold feet if the film hadn't been part of the deal.

“Looking back, I probably would never have done the trip if I hadn't been so deep into the movie, as well,” he said. “I'd told people about it, so I couldn't not do it.”

With the crew in tow (at $2,000 per day), Murray traveled from Milwaukee to St. Louis, Kansas City, Dallas, Santa Fe, Phoenix and Las Vegas on his way to Los Angeles. He went on hiking dates, tried skydiving and did a back flip off a trapeze, despite his fear of heights.

Not everything went according to plan.

After successful rendezvous in St. Louis and Kansas City, the rest of his dates bailed out, leaving Murray scrambling to find replacements.

He found no dates in Amarillo, Texas, so he spent time interviewing women about dating. One woman told him about an agreement she had with her boyfriend: He could sleep with other women as long as they gave him a ride to work.

“It was really trashy,” Murray said of the Amarillo scene.

By the trip's end, Murray felt good; he had five or six women who were interested in a second date. Unfortunately, the woman he fell for just wanted to be friends.

Bummed out, he returned to Milwaukee, shelved the documentary and went back to his job.

For six months, it gathered dust. Then he had a change of heart and began working on it again.

Did Murray ever find Ms. Right? That question will be answered at the film screenings.

Murray has emerged from the experience as an advocate for online dating. He said he expected to meet a bunch of crazy people, but that didn't happen.

“What I found … is that if you're generally nice to someone, if you're interested in them, they're generally going to be nice to you,” he said.

He also learned to overcome his dating insecurities.

“The bottom line is that most people have the same fears as you do,” he said, “so that's no reason not to ask someone out.”

“Dating America” debuted at the Milwaukee Film Festival last fall. Some viewers told Murray afterward that it inspired them to face their fears—whatever they were.

“I'm glad I did it now,” he said of the film. “I think it's really cool that it inspired some people to get off their asses and do something that was uncharacteristic.”

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