Hoping to find love – or at the least, a good story or two – a 34-year-old bachelor hits the road, scheduling eight different dates with eight different women across eight cities.

It sounds like the premise to a bad romantic comedy starring Patrick Dempsey and Katherine Heigl. Or perhaps a strange reality show hybrid of "The Bachelor" and "The Amazing Race" (don’t think somebody hasn’t pitched it). As it turns out, it’s neither. It was Bob Murray’s real life.

"Most of my long-term friends were married, and it was a weird year because a few of them started to have babies," Murray explained. "So you’re in Milwaukee at 34, it’s kind of a point in life where you wake up one day and realize your life is really routine and getting kind of stale. Nothing was changing. I was just doing the same thing everyday. You start to realize that it’s time to grow up a little bit, and I wasn’t going to do it living my life the way I was."

So Murray came up with a proverbial wrench to throw in his life’s usual routine: He was going to travel from Milwaukee to Los Angeles in a cab, setting up dates with women online in the hopes of finding the one. Everyone he told about his cross-country trip was fascinated with the idea, so as almost an afterthought, Murray decided to hire a crew to help film his expedition.

"When you think about the trip, it’s a pretty vain thing to do," Murray admitted. "I mean, to say, ‘I’m going to go on this trip, and I’m going to film myself.’ You really can’t get more vain than that. That was in the back of my mind a bit."

The results became "Date America," a documentary screening as a part of the Cream City Cinema program at the Milwaukee Film Festival. The film premiered last Saturday, but has two more showings, one tonight at the Fox Bay Cinema Grill and the other on Oct. 6 at the Oriental.

To find his romantic co-stars, Murray hopped onto an online dating website and scrolled through all the profiles located in each stop on his trip. He would then email the ones he found interesting or attractive, let them know about his trip and his film, and ask them out on a date. In the end, he found eight women not only willing to go on a date with him, but have it be filmed for the documentary as well. As you’d expect, there were some first date nerves, especially since Murray and his respective dates were not alone on their outings.

"They were really surprised when I showed up with a crew, which was two camera guys, a sound guy and an assistant," Murray said. "They thought I would just show up with a camcorder, which in my mind, would be really creepy."

In most cases, the early jitters went away, and the dates went charmingly well. But, of course, not all of the matches were made in heaven. One date in particular started poorly and never got much better after that. Murray even summoned the camera crew away to see if they were the problem, but after a date of short answers and even shorter eye contact, it was clear she had no interest in seeing him ever again.

"I kept her on the date for probably about two or three hours, and she wanted to be there for about ten minutes," Murray said.

That failed night out was the closest Murray came to a dramatically crazy date, something he actually hoped for when he originally began putting together the trip. However, all the women he dated were very genuine and down to earth.

"In reality, maybe they thought I was the crazy one," Murray said. "Maybe I was. Maybe that’s why they all seemed so normal."

Perhaps that was the case. By the end of the trip, there was a total of 120 hours of footage from the dates and on the road to go through, and not all of it was particularly flattering for its star.

"When I got done, I was like, ‘Aw sh*t, people are actually going to see this," Murray said. "I didn’t edit it to make me look like the best guy in the world. We kept a lot of things in there that were embarrassing to me. It’s tough when I watch it. Every time I see it, there are places where I cringe a little bit."

Despite his embarrassments and dating faux pas, Murray did end up meeting a woman that he fell for. And though the story didn’t take him in the path that he expected or necessarily wanted, according to Murray, it still turned out well (I leave it to "Date America" to reveal exactly how).

The journey also inspired Murray – already a fan of documentaries like 2007’s "The King of Kong: A Fistful of Quarters" – to pursue making another feature in the future. He already has a topic in mind: gay rights.

"The fact that gay people don’t have the same rights as everyone else is crazy to me," Murray said. "I can’t even believe that our society, as smart as we think we are right now, there can even be issues about things like gay marriage."

And as for the possibility of a sequel, Murray noted that he wouldn’t do it again, but there’s an opportunity for someone different to take the starring role.

"A woman’s perspective would be better because the women have all the horror stories about online dating. They’re the ones where they go on a date, and the guy is 20 years older than he said he was or he lies about his profession or having a family. Those are the really crazy stories you hear. So I think if a girl went cross-country and saw eight different guys, to me, it’d be really interesting to see how the guys would act."

So perhaps stay tuned for "Date America 2: Date Harder."