Who has not known a certain kind of sensitive guy -- the kind that always listens, that holds you when you're crying and loves you faithfully with never a hope of getting even a kiss in return?

On a recent weekday, he wanders Capitol Hill with a hopeful look in his eyes, trailed by a director with a video camera, trying to get someone -- anyone -- to go on a date with him. He is Dan Jacobs, 22 years old and certain that his 5-foot-6 stature turns women off. One woman says "Sorry" when he tries to stop her, in the curt fashion that people say "Sorry" to bums. Another looks so mean he doesn't even try. He sees a young curly-haired brunet with a kind face.

"Hey, 'scuse me -- do you have a minute?"

She stops, looking uneasy under the gaze of the camera. Jacobs tells her he's making a documentary about the dating life of a short, sensitive guy, and asks her what she's doing the next afternoon. A male bystander pops his head into the frame.

"Dang! You are crazy!" he tells Jacobs. The brunet takes advantage of the distraction to turn and run in the opposite direction.

"What did I do?" asks Jacobs.

In the annals of documentary filmmaking, there are surely few projects with as much potential for abject humiliation as "A Sensitive Guy on the Road." Jacobs's mission, which he hopes will end in love, is to go on a date with a different woman in each of the 48 contiguous states and in Washington, D.C. The District date -- if he can get one -- is to be his 10th.

He sees this project as a journey into the heart of the American woman, to find out what she really wants. He offers himself as the alternative to the macho bad boy: a guy who plays the guitar, does yoga and writes love songs.

"Girls are not sex objects for me," he says. "They're, like, people."

In sixth grade, Jacobs asked out a girl named Joy, who told him he was "too small," and instead went out with a bully named Tank. This seems to have been a defining moment in Jacobs's life. The way he describes it, women are always passing him over for guys bigger or badder than he is.

But on this particular day, what women might be noticing is not his size or soulfulness but the aggressively wacky rainbow-colored propeller cap he is wearing, and the miniature cello jutting from the breast pocket of his brown thrift-store suit. It's unclear why he has chosen this particular get-up, purchased this morning at a consignment shop in Alexandria, where two elderly salesladies told him that no, they would not go out with him.

Jacobs is a precocious version of the sensitive guy, not the timid kind who loves women from afar but the kind who befriends the ones he likes, shows them the beauty of an emotionally open, mutually respectful relationship--and then watches in horror as they date meathead football players. In person and on his Web site, FiftyDates.com, he points out that he's never kissed a girl without asking permission first. He reveals that he calls his mother "mommy" and that he once stayed with a girlfriend who cheated on him three times because he was trying to understand. Not too long ago, he cooked dinner for a female friend, and sang her some poignant songs he'd written.

"She cried," Jacobs says. "It was a really beautiful night."

Then he found out she had a boyfriend.

Jacobs is not an unattractive fellow. Under the cap, his dark hair is thick and rakish; his neck and biceps are sculpted from years of wrestling. He is energetic and says he used to get in trouble at Hebrew school for not sitting still. He graduated from Williams College in Massachusetts last January and worked briefly at a market research investment firm before deciding he needed something more creative.

At a friend's suggestion, he considered writing a sensitive-male column for a women's magazine, then decided he should make a documentary. He says he solicited investments from Williams alumni and others, gathering $42,000 of the $72,000 budget. He and his director, Jennifer Redfearn, went on the road in early October. He has conceived the film as a critique of reality dating shows, though truth be told, he doesn't watch them much and -- when asked -- has very little to say about them. But he knows that the male ideal presented on shows like "The Bachelor" is a tall guy, not too smart, very handsome, often rich.

There are also a lot of hot tub scenes on those dating shows. Jacobs says he doesn't plan to share a kiss with a woman until he finds one he really, really likes and who, hopefully, likes him back.

In Providence, R.I., he went on a date with seven feminists from an art co-op; in South Jersey, he went bowling with a tomboy. Only one girl really tempted him. She's 18 and a film student. He met her in New York City, and their first date "was, like, the most beautiful thing ever." He broke the rules he'd set up for the documentary (one date per girl) and went out with her several more times. He says he doesn't understand why she keeps agreeing to go out with him. She's "so too good for me."

Back on the corner of Seventh Street and Pennsylvania Avenue SE, Jacobs stops just about every woman who comes within his 10-foot radius. He tries a woman in her fifties, whose dry look says Yeah, right, and then an extremely pregnant woman in a peacoat.

"What are you doing tomorrow afternoon?" he asks.

She says she has Lamaze class.

He crosses the street and approaches a woman in a red top and leather pants. She sees the camera. She stops.

"This is a reality TV show?" asks Karen Davis. "I'm an aspiring actress!"

Davis, 27, is thrilled to be asked on a date. "Do I look that good today?" she asks. She offers to get her hair done. She gives him her number and blows him a kiss on his propeller hat. "You gonna call me?"

Jacobs promises he will.

Davis waits and waits. She never hears from the sensitive guy.

"He stood me up," she says a few days later. It turns out Jacobs has mixed up her number with someone else's and left a message for the wrong person. Davis sits at home and wonders what she did wrong.

"Maybe I was too excited when I saw the cameras and stuff," Davis says. "Maybe I need to get back on my Hydroxycuts or something, lose some weight."

Meanwhile, Jacobs charges on with his mission, determined to woo the nation's women with his sensitivity. He winds up going out with another woman he meets on the street, who is 42 and takes him to her church and tells him that shortness is a state of mind. No sparks there. A few days later, he and Redfearn, his director, decide they need a bigger crew and they return to Massachusetts, where Jacobs decides he will either raise more money and return with more staff and an RV or scrap the whole documentary and write a book instead.

But he vows not to give up on this mission.

After all, he says, "This is a journey for love."

Dan Jacobs and director Jennifer Redfearn, making a film about his quest to go out in each of the lower 48 states and the District, plus one final date.Karen Davis blows a kiss to Dan Jacobs after they agree to go out, getting Jacobs that much closer to his national goal.