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Gen Y Wanderers: An Interview with Dating Documentary Filmmakers Alicia & Megan

50/50's Honda Fit

A treat today – below is the interview posted on Wanderlust and Lipstick’s blog about Gen Y Wanderers. Questions are by the charming Alana Morgan, answers by me (A) and Megan (M). (Whoa, am I Gen Y? I always thought I was sort of XY…) In the words of Jen Friel, hit it Alana! 

Today’s interviewees have added a twist to trying to figure out your life through travel – they’re constantly dating while doing it. Alicia Ostarello, 30, and Megan Pratt, 23, have just been on a road trip across the continental U.S. questioning, filming and searching for love.  After being broken up with by a boy, Alicia realized she needed to do something different when it came to dating.  So, as you do, she set out to make a documentary, 50/50, going on a first date in all 50 states.  The documentary, set to release next summer/fall, studies dating in America but is also a look at the country through the lens of bachelors and bachelorettes in a very real way.  What is the same from Seattle to Savannah? What is different?

Here, both Alicia and Megan have shared their answers to the same questions to see where their perspectives meet and where they differ.

Where do you call ‘home’: 

Both of us call the East Bay home (in the San Francisco Bay Area).

Do you miss home?  What/why?

    • A: I definitely miss home. To be fair, I actually don’t have a home – my roommate moved out and put my stuff in storage, so in some sense I don’t really have a home to miss. When I started I really missed my familiar routine, but when we had a routine on the road (or the routine is no routine) I was actually okay. I do miss being involved with my friends’ daily lives and having adventures with them, but that’s sort of silly – I am missing moments that didn’t exist before I left, if that makes any sense. This will sound so cheesy, but I want to believe home is where you make it, regardless of actual location. I know Megan might disagree, but I want to be able to feel a sense of home no matter where I am. Still working on that…
    • M: I think you always miss home whenever you are on the road for a long period of time.  Besides my friends and family, I miss the food.  You get very used to eating a certain way, and when you can’t meet those desires, your body has a habit of freaking out a little bit.  Things are better now on the East Coast, but especially through the Mid West, I think both of us were sorely missing vegetables.


Where has been your favorite stop and date so far?

    • A: Hmmm. My favorite stop was Nashville. Megs and I had a few hours to wander around the city and do some touring, and we saw things I had no idea existed, like Andrew Jackson’s home with a different interpretation of his history than we were taught in school in California, and a full scale replica of the Parthenon! Seriously! My favorite date…oh gosh, I can’t decide…
    • M: My favorite date was when we utilized our partnership with ZOZI to go on a plane flight over Chicago.  It was a stunning day with large fluffy clouds interspersed in a blue sky.  The date on that day was also a very nice guy.  Alicia was sort of freaked out because she hates flying, but as a filmmaker, watching her interactions with her airplane-loving date with such a stunning backdrop was fantastic.

How old were you when you made your first big trip or visited another country?

    • A: My parents took my brother and me on road trips every summer until we were teenagers – like, crazy long 4-8 week summer trips with lots of camping, historical monuments, national parks, and museums. We drove to Nova Scotia and back on our longest journey. So national travel has been ingrained in me. However, I didn’t leave the continent until two years ago, which is pretty weird in retrospect.
    • M: My family traveled a lot growing up, but I would point my wanderlust to a trip to Italy I took with my aunts when I was 12.  I still think that is a perfect age to take kids traveling.  They are old enough to know what they are looking at is special, but aren’t cynical about the world or what they’re seeing.

Where has been your favorite place to travel?

    • A: That whole Nashville thing. Or maybe Utah…I could not get over the beauty of Arches and Zion, and I’d give almost anything to go back and spend a few weeks there.
    • M: I really enjoyed Duluth, of all places.  As a Californian, I am not used to seeing the leaves change colors.  At home, if a tree turns red it would be a major sign that the tree needed to be cut down immediately.  But in Duluth, the trees turn a thousand different colors of yellow and red all the way to horizon.  I had a sudden affinity for the tree tourists who flock out of the cities to go look at the colors.  I really want to join them next year.

Alicia Ostrello and Megan Pratt

Least favorite?

    • A: I’ve liked everywhere. It’s impossible to compare any two places…well, that’s not true. It’s very possible, but it is silly. Every state is different. The landscape changes, the culture changes, the people change, and yet we all have a lot in common somehow. I think my least favorite food was Duluth, but that may definitely have been our own fault.
    • M: Indiana.  It felt like many people left the state to the wind.

Good book recommendation to read while traveling: 

    • M: My suggestion for a good travel book is anything that involves traveling as well.  On this trip we listened to the full cast recording of American Gods by Neil Gaiman.  There is something very enjoyable about having an amazing story read to you, as you pass through the very towns its set in.
    • A: Totally what Megan said. I’ve been working on Steinbeck’s Travels with Charley myself, and the same thing applies. Interesting story and observations about the country, and it’s fun to see where I totally agree with him on the American landscape, and where I totally differ. Totally. We also listened to Gaiman’s Neverwhere in one sitting from Dallas to El Paso, which was a treat.

Why do you think it’s important for our generation to travel?

    • A: I think the experience of realizing we are all in this together (this being life, being on Earth, being in America) is really powerful. We met a man in Virginia who was so opposed to California in general, and I wondered how someone could so easily want to dismiss me based on where I lived. At the same time, the man was congenial and welcoming. Travel makes me want to help people more, to connect with them and understand them and share that experience. If the only way you see other places is through a screen on a TV or an iPad, you don’t actually know what’s going on…you just get the producer’s version.
    • M: I think its important to for everyone to travel.  Meeting knew people challenges your point of view and forces you to step outside your comfort zone.

Do you think the idea that Millennials are lazy/slackers/commitment-phobes is true?  Why or why not?

    • A:  I think there is a cultural shift going on in what is important to us as people, what is important in life, and how we want to live. The Baby-Boomers were raised by people who survived the Great Depression, and thus were instilled with the value of working hard and long, joy aside. The Baby-Boomers thus made a lot of money but weren’t happy, and passed a concept of “do what you love” to Millennials because they weren’t always able to engage in that. And now the Millennials are seeing “Do what you love” becoming the ultimate trainwreck (which I imagine will lead to raising our kids with stronger work ethics).  Are Millennials as a whole slackers/lazy/commitment-phobes? No – they’re a product of the culture that raised them. I think the issue here isn’t to point fingers at our parents though, but to look around and say “okay, so how do we fix this mess.” And I see every day that 20- and 30-somethings are looking for work/life balance in unique and interesting ways. Making films about dating in America, founding start-ups, working two jobs to make ends meet, volunteering in their communities, voting. Just because Millennials are placing a premium on balance and happiness doesn’t make us lazy. Just because we’re openly exploring concepts like polyamory or open relationships doesn’t make us commitment-phobes. And just because we’re refusing to work for people who treat us poorly doesn’t make us slackers. I think if everyone could look at the cultural context of how this is all working, they’d have a better understanding of why older generations think we’re flailing, and we’d understand why we’re baffled by the older generations.
    • M: This is something that I think gets lobbed around a lot by those older at the early 20’s age group.  I actually see it moreso in those who are in their early thirties.  People my age have grown up under a country at war, and one of the worst economic collapses in 70 years.  I think any dream we as a group had about things being handed to us died in 2008 when we saw our futures fall at our feet at the age of 19.

One travel tip:

    • A: Carry real maps (just in case) and don’t be afraid to ask for directions. And always have extra water. I’m apparently bad at one tip.
    • M: Always have snacks and eat real meals whenever possible.  Food might not be readily available whenever you want to eat and just carrying power bars will make you feel that much better.

What’s something you wish you had known before you started 50/50?

    • M: Bring snacks!
    • A: That Megan drives really fast. :-) Honestly…hm. I guess I wish I had known that I was going to want to spend more time everywhere. I didn’t realize I would be so enamored with each place and desire to get off the beaten path and see more. It can be really frustrating to know there’s so much I’m missing, and that makes it hard to be in the moment.

What is the most important thing travel has taught you?

    • M: Simply being polite will get you through most situations.  Also, don’t be afraid to leave if you don’t feel safe or don’t want to be with those people. You are mostly likely never going to see these people again, so don’t be afraid to move on.
    • A: So right on about politeness. That goes for the people you meet regardless of how much time you spend with them, people whose floor you are staying on, or the people you are traveling with. I think Megs and I work well together on the road because we strive for politeness in the little things and not taking one another for granted. I also think travel continues to teach me we are all human. Everyone is flawed – from me, to my mom to strangers on the street. If we can approach each other with compassion for humanity, I think interactions in general go a lot better.

Where's Waldo?Where is the world is….

What do you think you’d be doing right now if you weren’t traveling?

    • A: Hmmm. Probably just working on my start-ups, Copy Muse and Vow Muse (writing businesses). And be dating a lot, just locally.
    • M: I would be working on films or commercials in the SF Bay Area.

Want to learn more about Alicia’s dating experiences?  Check out 50/50 on Facebook and Twitter.

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