Getting dumped sucks. It's a personal insult, even if the dumper cares about the person he or she is dumping. The action says: "I don't like you. Well, not enough."
Heart rip to road trip 041713 NEWS 1 Capital City Weekly Getting dumped sucks. It's a personal insult, even if the dumper cares about the person he or she is dumping. The action says: "I don't like you. Well, not enough."

Photo Courtesy Of 50/50

Alicia Ostarello, left and Megan Pratt take a walk on local beach while in Juneau for the Alaska segment of a documentary film they are making chronicling 50 first dates in every state.

Wednesday, April 17, 2013

Story last updated at 4/17/2013 - 2:16 pm

Heart rip to road trip

Getting dumped sucks. It's a personal insult, even if the dumper cares about the person he or she is dumping. The action says: "I don't like you. Well, not enough."

That's the message Alicia Ostarello received about a year ago. Ostarello is cute, spunky, sassy and lovable. She lives in the Bay Area and was working as a writer when she got the message: You're not good enough for me.

Some of us reach for ice cream, Kleenex, spend nights in a hot bath with ice cream and Kleenex. We might get our friends to tell us how wonderful we are. Ostarello knew she was wonderful, at one thing in particular: first dates.

"I was disenchanted with my job," she said. "I had this idea on the top of my list, that I wanted to go on 50 first dates."

She said it was more of a joke, at first, but it became more plausible the more she thought about it. She had a car, she had some savings. But as the prospect of going on a first date in all 50 states became more realistic, she was terrified.

"In a good way," Ostarello said. "In a this-might-be-a-terrible-idea-in-a-bad-economy sort of way, or in a this-might-be smart-in-letting-me-heal way."

She decided to take on the project and planned to write about it. She contacted a friend of hers that she thought might have connections to people in the publishing world. Her friend gave her one suggestion: make a film.

The friend connected her with Megan Pratt, who had recently graduated from film school.

"My thought was, 'Get in a car with this stranger for two months? That sounds like a terrible idea,'" Ostarello said. "About an hour later I thought it was a good idea."

That summer the duo teamed up, and began scheming about their adventure.

"Then in a fun twist of fate, the boy that broke my heart came back (to me) and we started dating," Ostarello said. "I didn't tell him about the project, though he knew I was working on something."

He dumped her again, and the next day Ostarello and Pratt began an online fundraising campaign to fund their adventure. They met their goal in July of 2012.

"I was like, 'And here's my middle finger,'" Ostarello said, to the guy that broke her heart. "I'm pretty sure he got the message."

Ostarello gave her notice at work in August, and she left for Oregon with Pratt in September.

"We approached mathematicians to figure out the most efficient way to do this," Ostarello said. "We took pins and stuck them in a map of the U.S.; put them in places where we knew people and/or where we wanted to go. Then we took a string and stringed together routes, and said, 'That will work, no that won't...'"

Pratt said it took them a full day to string out the route. They put their route into Google Maps.

"I made the World's Best Chart, with everything from a budget to the cities, how far we had to drive, the date, day of the week, where we were staying, if there was a date that day," Pratt said.

Ostarello used online dating sites like OK Cupid, How About We, and Craig's List when she was desperate. The team also relied on networking in various towns. They learned that securing dates with men willing to be filmed required strategy. They wanted to plan ahead, but giving the men too much time to ponder what they were getting into turned out to result in back-outs.

As they rallied around the country in Ostarello's Honda Fit, they developed a routine.

They took turns driving, and as Ostarello was on various dates, the camera equipment set up, Pratt would monitor the footage while working on finding hotels and date venues that would allow them to film. Pratt said the dates were varied, lots of coffee and dinner dates, but some walks, a rock climbing date, a ghost tour in Savannah.

One hard part, Ostarello pointed out, was that she'd either be into the guy, and want to spend more time with him, or want to bail before the mission had been completed.

"Sometimes the guys liked Megan more than me," she said.

Pratt said she didn't feel like the camera equipment affected the course of the dates that much. She said that disclosing they were making a film weeded out the squeamish.

"I think the guys that say 'Yes' to this are ones that tend to me more outgoing; they're ones that generally say 'Yes,'" Pratt said.

After driving for 16,000 miles, Alaska was the women's 49th state. They choose Juneau, and arrived the first weekend in April.

"We picked Juneau because Ketchikan is too tiny and Anchorage looked hella boring," Pratt said. "I'd been through here once before, on a cruise ship. It kind of reminds me of my own home town if you took it away from everybody else for while and let it cook on its own."

Ostarello had set up a date with a local man, Alaskan Man No. 1, through OK Cupid for Saturday afternoon, soon after they arrived to town. He backed out the day before.

"He didn't like the concept that I was coming in and leaving," Ostarello said.

"He seemed like he had some bad luck recently and over-reacted that Alicia was casually dating someone back in the Bay Area and that she's going on two dates in Alaska," Pratt said.

Ostarello had been in contact with Alaskan Man No. 2 online, but he had backed away after hearing about the film, got back in contact with her and suggested a friend of his, Alaskan Man No. 3. Ostarello got in contact with No. 3, who said he had no plans, and she texted him at 2:30 p.m., suggesting they meet at the Alaskan Brewery at 3 p.m. He didn't show. He texted that he was skiing.

"We were talking to the bar tender and a guy walked in," Ostarello said, (Alaskan Man No. 4). "He said he recognized me (from an online dating service) but hadn't responded because the project sounded weird. They took a poll in the Brewery.

The bar tender yelled, 'This girl is from California and she is waiting for her date. He put her off to go skiing. Should he be allowed to come down here and go out with her?' and everyone said no. To be fair they did say the powder is really nice right now.

Eventually Alaskan Man No. 3 walked into the Brewery. Coincidentally he was neighbors with Alaskan Man No. 4.

"They started talking, and (Alaskan Man No. 4) said, 'Hey, I'm hanging out with this cute girl and she got stood up by someone,' and (Alaskan Man No. 3) said, 'That someone is me,'" Ostarello said.

No. 4 politely bowed out, and Ostarello and No. 3 spent some time at the Brewery and then went sledding.

"I feel like I took to it well," Ostarello said, of her first sledding experience.

The guy suggested dinner, but Ostarello said she was already put off by his tardiness earlier that afternoon. They stayed with some family friends in Auke Bay Saturday evening. They went to the Mendenhall Glacier the following day before meeting up with Ostarello's second Juneau date.

Alaskan Man No. 5 and Ostarello had lunch at the Silverbow Bakery and then went to the symphony.

"He was very interested in numbers," she said, but didn't elaborate much further.

Both Ostarello and Pratt enjoyed their trip to Alaska's capital city.

"Date-wise, it's been special," Ostarello said, "But town-wise, it's been fantastic. There have been very few towns that have been so accepting or welcoming."

After leaving Alaska the women headed back to the Bay Area, where they'll work for a month and begin planning their trip to Hawaii to finish the adventure.

Pratt said Ostarello developed her game through the process.

"She got really good at giving the 10-second answer and then asking, 'Tell me more about your dog,'" Pratt said.

"I wanted to get information from them," Ostarello said. "Why they were online, what dating was for them. Some of the best dates I had were when we didn't talk about dating at all, like past relationships. Guys would recognize that I'd likely talked a lot about dating."

There were guys Ostarello said she'd like to follow up with, like the man she met in Utah. Then there were, of course, hitches, hilarious moments and really bad dates.

They witnessed anger aimed at immigrants, tension between residents in California and Texas; a man in Virginia had an inflated case of state pride and a man in Mississippi chewed Pratt out because he thought California had too much state regulation. Every 10 days someone thought they were making a pornographic film.

The worst date, a story the pair said they've told over 50 times but is still funny to them, took place in Ohio. Ostarello met a guy at his family's restaurant. The man's parents, sister and brother-in-law were at another table in the venue.

"First, he was rude to the waiter," Ostarello said.

"Then he criticized the chef," Pratt said.

"Then he was nice to me for a second," Ostarello took up the story. "He said, 'You know, you're not as Jewy as I thought you were going to look, but you're still pretty. But my mom says I like funny looking girls.' I went and tried to hide in the bathroom."

The Ohio date talked about a kill list he maintained in high school, and requested to be alone with Ostarello. He asked when the cameras would be removed. He suggested rolling Pratt up in a carpet and throwing her in a ditch.

"That was oddly specific," Pratt said.

"Megan asked how things were going, and I said, 'A, he wants to kill you, and B, he wants to play the accordion for me,'" Ostarello said.

He sent the couple's leftovers to Pratt, and took out his accordion. Pratt said she was ecstatic.

"There were times I wanted to be her friend but for the sake of the film I had to throw her under the deep end," Pratt said. "He was playing the according and making this face, like a duck or a fish, you can't capture it in writing."

The Ohio man mentioned he was actually a rapping accordion artist, and started including lines like, "I'm always like a Maxi Pad" into his musical show.

"Then he tried to kiss me," Ostarello said. "After I backed away I told him 'I don't kiss on first dates.' He said, 'Me either.'"

Ostarello said she matured over the 49-state tour, developing a thicker skin.

"I literally think part of why this happened, why I had this idea, is I was doing the man-speriment," Ostarello said. "I did things like I didn't give a (care), didn't over-analyze, didn't obsess over those kind of things."

But, as Pratt attested, Ostarello did take things seriously.

"She really makes an effort to connect with everybody she meets, almost to the point where she's hurting her own mental movie," Pratt said.

"It's been life-changing," Ostarello said. "It's changed the way I view relationships. Not my personality but my inner monologue, how I interact with other people."

Pratt also said the project has had an overall positive effect on her.

"We met a lot of really wonderful people," she said. "I think (we) have a much better impression of America than when we stared the trip. People were just very, very wonderful. A nice woman in Kentucky gave us a tomato. We made this joke that Americans are the heroes, and this (movie) will never sell."

The team plans to hand over the footage to a professional editor once they've returned from Hawaii. Additional footage from activities like a guest appearance on Neil Strauss's radio show, (Strauss wrote the well-read book on seducing women, "The Game: Penetrating the Secret Society of Pickup Artists"), will be included. They will be looking for an investor for the post-production process and hope to get the film into the festival circuit.

"It was exhausting, but things can be good and be exhausting," Ostarello said.

For more information on the project "50/50," visit:

Amanda Compton is the staff writer for Capital City Weekly. She can be reached at