Health & Medicine

Frustrated dater goes on the road, filming his search for love

Bob Murray, 34, is taking a cab — and a documentary film crew — from Milwaukee to Los Angeles in search of a significant other. He is going on dates with women he met online.
Bob Murray, 34, is taking a cab — and a documentary film crew — from Milwaukee to Los Angeles in search of a significant other. He is going on dates with women he met online. MCT

MILWAUKEE — Don't pity Bob Murray because he hasn't found The One.

Envy him. He has found a way to make his search for romance fun and — if he's really lucky — profitable.

Murray, 34, is looking for love in what he hopes are all the right places between Milwaukee and Los Angeles. The commercial real estate investor is on a 17-day road trip, visiting eight cities and going on nine prearranged dates with women he contacted online.

Even if he doesn't get a sweetheart, he hopes to get a sweetheart film deal out of the journey. Murray will travel with a film crew, and he plans to make a documentary and peddle it to film festivals.

"I love adventure," he said.

Frustrated but inspired by the successful online relationships around him, Murray figured it couldn't be that difficult to find somebody somewhere else and feel a spark.

Murray, who has been unattached for a year, will meet prospective girlfriends in St. Louis; Kansas City, Mo.; Dallas; Santa Fe, N.M.; Phoenix; Las Vegas; and Los Angeles, plus a yet-to-be- determined city in Oklahoma. It's not as if Murray has any issues that would prevent him from dating without a cross- country tour. He thinks he has just been in a rut.

"In the last 12 years, I've been in three long-term relationships," said Murray, who called the past year as a singleton "the longest stretch since college."

"You're not going to meet somebody at a bar," he said. "And if you live in the city for a long period of time, you dig in and have your friends. You meet fewer people as you get older."

He said he wanted to gauge his relationship status and find out "if I was single because maybe Milwaukee's not my type of city, or if it's just me."

In Murray's case, traveling single doesn't mean solo. His movie crew from Chicago includes two camera operators, a production assistant and a sound guy. And he's making the 17-day journey by cab.

Murray said his cab driver, Paula Heus of Milwaukee, also will be a sort of "life coach."

"She's a real firecracker and not afraid to state her opinion about things," said Murray, who wanted a woman among his all-male crew to help put his dates at ease. He's asking a lot of those dates as it is: Be comfortable on camera, sign a waiver for filming and go out with a stranger from Wisconsin.

Before he was even out of the driveway, Murray had hit a couple of bumps in the road. Two dates fell through because the women found boyfriends in the interim (new rule: Set up dates only two weeks in advance), and he couldn't get anyone to respond to his date queries in Amarillo, Texas, which is now off the tour.

He had hoped to raise $20,000 for the project through a video request ( and YouTube but netted less than $5,000, so he took on a major portion of the funding himself and went back to the people who donated large sums to ask for more. In return, they receive equity in the film.

None of these roadblocks has slowed his pace. He recently kicked off the project with a first date in Milwaukee, in which he took Cynthia Kmak (occupation on Facebook: actress) out for an afternoon tour of a brewery, followed by dinner, accompanied by his film crew. The evening ended with a trip to a miniature bowling alley — although the cab broke down along the way.

It's all part of the adventure, Murray said on his Date America site on Facebook ( He's documenting his hits and misses on Twitter (!/dateamerica).

He has made plans for other cities. In Phoenix, he's considering a hike on Camelback Mountain. He expected skydiving to be included in at least one date. Each encounter could be six hours long, he said.

To meet women, Murray registered with national online dating sites including and He said he's honest with the women he talks to and tells them upfront what he's doing.

"It started as a cab trip, and I thought it'd be a fun adventure," Murray said. "And you know what? Nobody's ever done a documentary on online dating."

Well, Murray hasn't. At least not yet. "