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Farrell Parker (Jen), Suzanne Edgar (Victoria) and Vaughn Irving (Phil). Photo by Ryan Maxwell Photography

As February teaches us, there are basically three ways to observe Valentine’s Day. You can embrace it in all its red, heart-patterned cheesiness, ignore it, or rail against love and capitalism in a thinly-veiled defense of your bitter loneliness.

A Valentine’s Day weekend opening turned out to be perfect for Flying V’s world premiere (expanded from a previous Fringe version) of You, or Whatever I Can Get. The characters’ approach to dating in this hilarious and relatable musical is similar to how people deal with Valentine’s Day: There are two hopeless and slightly pathetic romantics, an anti-love jezebel, and a dude who just wants to play video games and eat Cheetos.

We open with Phil (co-writer Vaughn Irving), our sweet protagonist whose heart is quickly crushed by the longtime girlfriend (the dulcet-voiced Autumn Seavey Hicks) for whom he just bought a ring. Retreating to the apartment he shares with his free-loving sister Jen (confidently played by co-writer Farrell Parker) and sweet-as-apple-pie college friend Victoria (co-writer Suzanne Edgar), Phil breaks into an angsty rock song in which he wails, “I’m 30! I’m gonna die alone.”

Phil’s best friend Dennis (co-writer Doug Wilder), newly single and thrilled to be crashing on Phil’s couch in his boxers, is that friend for whom February 14 is just another day. Jen is the one actively protesting it. Trying to convince Phil to enjoy his freedom, she extols the virtues of an unattached lifestyle in a jaunty, upbeat tune. “Being single is not so bad! You won’t believe the night I had,” she sings, with a strut and a wink. “Dinner with Daniel and drinks with Joe, then we had sex in a car2go.”

It’s one of the many numbers that places this production solidly in 2016. In another song, cast members rattle off the names of online dating sites.

Musical Director and Co-Writer Steve Przybylski keeps the music fresh and varied, switching styles faster than Jen picks up new partners. Audience members hear rock ballads, sultry, cabaret-style solos, Alanis Morissette-style “chick rock,” a Sublime-inspired ska-reggae song about getting high, and a rap, enthusiastically delivered by Wilder.

You, or Whatever I Can Get is a show about, and created by, millennials. This highly entertaining, poignant play is pulled directly from the writers’ experiences, and the music itself speaks to their generation.

And while many musicals painfully wedge in boring and unnecessary songs solely to keep the cast singing, that’s not how this production came together. In an interview with DCist, director and co-writer Jason Schlafstein says the team started with the music, and let the plot evolve from there.

“What we found working on it was that whenever we tried to force a song to just be plot, it didn’t work,” he says. “The songs had to be about really personal intimate moments, and then there were moments in the songs that would advance everybody’s plots forward.”

The result is a lively soundtrack that leaves audience members engaged and laughing.

This new staging is longer and more fleshed out than the version that ran at the 2014 Capital Fringe Festival, when the production won the award for Best Musical. The six-person writing team added songs and clarified relationships, such as the one between Jen and Phil; during the Fringe run, the characters were just friends.

“We got very stuck in the romantic relationships the first time through,” Irving says, “and this allowed us to not only deal with this brother-sister relationship, but also open up the door to our parents and what our relationships with our parents are and how that has affected us as adults.”

In a serious, reflective duet (“Do You Think They Fucked Us Up”), Phil and Jen ask themselves whether or not their parents’ divorce sparked their individual responses to love. Phil clamors for intimacy, while Jen eschews it.

But even if baby boomers don’t use Tinder, they can still relate to the confusion and hurt feelings that are part and parcel of dating.

“The mode in which we go about [dating] is different, but a lot of the insecurities and the heartaches and the issues—our own personal demons are the same across the board,” Irving says. “At its core, yes, the show is about dating, but the show is also about loneliness and trying to make a connection, and I think that is the timeless side of it.”

You, or Whatever I Can Get plays at the Silver Spring Black Box through February 27. Tickets are available online or $20 at the door.