On the road to nearly 50 first dates

Well, nearly 50, as Don Jacobs' quest to find love takes him across the country. In Baltimore, he meets a red-headed stranger. And...

October 23, 2004|By Stephen Kiehl | Stephen Kiehl,SUN STAFF

This is not working.

Dan Jacobs has been standing outside the ESPN Zone for 45 minutes, waiting for his date. She was supposed to be his 11th date in a search for true love that is taking him across the country.

"It looks like my date has stood me up," Dan says. "This has never happened before."

The road to love is filled with potholes, especially for a nice guy like Dan. Plenty of girls want to be his friend; too few want to be his date. Still, he continues onward, seeking the answer to a question that has plagued him: Why don't girls ever go for a sensitive, love-letter writing, guitar playing, yoga practicing guy like him?

So he's making a documentary film titled A Sensitive Guy on the Road: Fifty Dates Across the States, and his every move is recorded on digital video by his director, Jennifer Redfearn. He's dated a radio DJ in New Hampshire, an underage beauty queen in Maine (she told him she was 18; she wasn't) and a feminist artist in Rhode Island.

"I would like to date a dominatrix," Dan says, in all sincerity. He is 22 and cannot even tie his own tie. "I think that would be a lot of fun. I would also like to date a cowgirl and a potato farmer from Idaho."

He's set up dates in some of the states he'll visit, but he arrived in Baltimore on Thursday morning without a prospect. So he walked around downtown and eventually found a woman willing to spend four hours with a man she'd never met before.

But the woman - he can't remember her name - isn't here. Big surprise. Now what? Dan sees a pretty redhead - jeans jacket, pink scarf, stylish brown leather shoes - heading into the ESPN Zone in downtown Baltimore. He runs after her. "Miss? Miss?" She stops and lets him approach.

He's wearing a striped blue shirt, black pants and green flip-flops. After some small talk, he explains his premise: "We're trying to see if women are willing to defy reality show stereotypes and go out with a nice, sensitive, albeit short, guy like me."

She says she has to go into the restaurant to drop off a job application and asks if she can give him an answer when she comes back out. Remarkably, she returns. She agrees to go out with Dan, as long as the date will be over by 8. She has to get to a soccer game.

Deal, Dan says. He has four hours. He will make the most of them.

Dan's first love was a brown-eyed girl, Joy, in his sixth-grade class. He had never spoken to her, but he knew he loved her. One day on the playground, he screwed up the courage to tell her how he felt, how he loved her and wanted to be with her. She laughed and said, "You're too small."

Then there was a girl he met in high school. She was a year older than him, and she was perfect. Dan decided to skip his senior year of high school so he could be with her. He persuaded his school, in Santa Monica, Calif., to let him graduate early. A month later, the girl dumped him.

A succession of failed loves are detailed on Dan's Web site, fiftydates.com, and he says that he came to realize one thing: "Pretty girls, the kind that make my heart go pitter-patter, just don't look at me in that way."

We'll say this about Dan: He's not a bad-looking guy - shaggy black hair, brown eyes, a nice smile. He's short, about 5-foot-6, but he doesn't seem to mind. He wrestled in high school and college. He's goofy and funny. He laughs easily. He always wondered why he had such trouble with girls.

Then, this past January, he graduated from Williams College and went to work doing investment research in Williamstown, Mass. He had time at night. He watched reality television. A lot of reality television. And he came to realize - the guys on the shows didn't look or act like him at all. They were tall and tan and muscular. They slept around. They were jerks. Yet the women fell for them.

Dan couldn't understand this.

"You ask a girl what type of guy do you prefer, and they say, `A sensitive guy,'" he says. "But then you ask what kind of guys have you gone out with, and they say, `Bad boys.'"

Determined to prove those perceptions wrong, and to show the world that nice, sensitive guys are worth dating, Dan came up with the idea for the film project. Through the Williams College network, he found some people willing to help him, and he raised $42,000. (He estimates he needs another $30,000 to complete the project.)

"My goal is to figure out what the heck love is for me," he says. "Maybe I'll be able to find that spark that leads to true love. Maybe I'll better understand love in general. And, at the very least, I'll find 50 friends."

Dan's date in Baltimore is Lindsey Wiest, 22, a recent graduate of the University of Tennessee. The plan is to go to the aquarium, see the dolphin show and then have a romantic dinner for two (plus photographers and a reporter) in Little Italy. First, though, they must attach a wireless microphone to her sweater and run the cord under her shirt. Luckily, she studied broadcast journalism in school and knows her way around a wireless mike.

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