Lyft claims it wants to be more than just a taxi service — it wants to connect people. Is it this generation's version of hitchhiking?

"This is a bit of a cluster," Lena Moreno says as we close in on the intersection of M and 29th Streets NW in Washington, D.C. The upscale Georgetown neighborhood is known for its congestion almost as much as for the Kate Spade, Ralph Lauren and other high-end stores lining its uneven sidewalks. The traffic is even worse on Halloween night as superheroes and villains spill out of the bars, ignoring cars and crosswalks alike. Moreno, a 26-year-old driver for the ridesharing service Lyft, peers through the windshield of her 2008 Nissan Versa. Her thick, rimless glasses look just like Martha Plimpton’s from The Goonies, but they’re not part of a costume.

I'm more than a little nervous—less so about the stranger driving the car than those we'll pick up on a night generally known for mischief and mayhem. Moreno doesn't share my fears. "For me, this is less sketchy than a cab any day," she says. Passengers have to create an account and input their credit card information before they can hail a Lyft via the company's app. "If something were to happen, that person could only get away for so long."

Moreno seems more disheartened about saying goodbye to her passengers than the odds of encountering a bad apple. “I've met so many people where I'm like, 'Ah, I wish I was your friend,'" she says, turning her head to check for traffic. It surely helps that after two months of stop-and-go communications with Lyft's San Francisco-based headquarters, I have been offered a ride along with perhaps the friendliest D.C.-based driver in this fleet of privately owned vehicles.

Some companies pride themselves on customer service. Lyft takes that concept a step further with the motto, "Your friend with a car," promising both drivers and passengers more than a pleasant business transaction. Each ride is a chance to strike up a meaningful conversation, to expand your social circle through an honest-to-goodness face-to-face interaction. Lyft and its drivers are out to give you the ride of your life, but personally, I'm just hoping it won't be my last. There's a reason I didn’t tell my parents about the ride along before I set out to discover whether Lyft represents sensible shared transportation or a Lifetime movie in the making.

If Lyft is already operating in your city, you will have noticed the giant fuzzy pink fender mustaches that the company provides its drivers (along with $1 million liability insurance). Moreno has further redesigned her vehicle as a mobile conversation piece. Instead of an air freshener, a black sparkly skull sporting a miniature pink mustache dangles from the rearview mirror. A young Bill Murray in Stripes gazes up at me from a pin on the dashboard. Moreno's job is to get you to the party, but if she can’t join you, maybe she’ll become an anecdote over kegs and cocktails.

If all else fails, no one can resist her snacks. A group of costumed American University students descend on the Trader Joe’s Milk Chocolate Covered Peanut Butter Pretzels en route to a bar at the outer edges of Georgetown.

"Thanks, honey," one of the girls says through a full mouth.

"You’re a winner,” says the same girl, or maybe another. Without turning my head, it's difficult to tell whether the youthful voices belong to "Meryl Streep," or "the 90s," or "Ponyboy" from The Outsiders. Moreno tells the girls the book was "way better" than the movie, which leads to a debate about its author.

"I knew it wasn’t J.D. Salinger." Whoever is speaking conveys both wisdom beyond her years and the effects of ritualistic pre-gaming.

Lena Moreno. (Photo: Vicki Valosik)

We swing a U-turn and pull directly in front of the bar. "Stay golden," the voices urge as the car door slams shut. Their largely quiet male companion, a Teenage Mutant Ninja Turtle, seems to follow their lead.

Moreno closes out the transaction on an iPhone mounted to the car's inner windshield. She says she’ll get an 80 percent cut of each fare, or Lyft’s $15 hourly rate ($25 for early morning or late night "power hours"), whichever amount ends up being higher. Since Lyft fares and tips operate on an honor system of "suggested donations," Moreno never knows exactly how much she'll make until she gets a summary the next day. She's not worried; she uses the Lyft app to rate passengers just as they rate her. If a passenger or driver gives the other three stars or less, Lyft never pairs them again. Moreno's passengers usually see stars—all five of them. She's earned enough money since she joined Lyft in August to move out of her parents' house just over the Maryland border and into the District proper. The flexible hours complement her freelance work composing music for visual media, which she hopes to turn into a full-time career.

Another Lyft order pops up on the iPhone, and Moreno hurries to respond in the allotted 15-second window before she loses out on the fare. The countdown isn't as intimidating as the traffic she faces on the way to Petworth, a D.C. neighborhood well north and east of Georgetown. I settle into the heated massage pad that Moreno bought for the front passenger seat as she ever-so-slowly maneuvers the car past a bad stretch of traffic.

"It's bold of you to work tonight," says Sadie, the latest passenger, when she gets into the car. She's off to her third engagement of the night, and she’s as bouncy as her hair, a jumble of curls deliberately masquerading as Baby's perm from Dirty Dancing.  

"Lena! Where’s your costume?" she admonishes.

Moreno has left her “Baberaham Lincoln" getup in the trunk while she’s on duty. "I was thinking about putting on the beard and the hat and being a hipster," she says. She would fit right in with the crowd at Sadie’s final destination, but instead, she drives off in search of a 7-Eleven. Moreno hasn't yet used any of the nine minutes of break time she accumulates every hour. It's almost midnight when she gets her coffee. We idle in front of the National Zoo until a call comes in. Then we're off to the next destination. And the next.

She originally planned to work until 3 a.m., but Moreno scaled back her shift, concerned that a late-night passenger full of pumpkin beer and candy corn might vomit in her car. So far, we’ve transported seven twentysomethings without incident. There’s still time for that, I think, as what can only be described as a trio of "bros" cross 14th Street and pile into the Nissan. They're drunk, they're loud, and I hope they're not handsy.

"So, driver, give us your spiel," one of the bros demands amid talk of the concert they attended and the amount of alcohol they consumed. To my surprise, they seem genuinely interested in Moreno’s work in film and television production, and they share the same enthusiasm for Game of Thrones. They're jealous, and almost reverential, that Moreno has only just started the third and “best” novel in the series.

"It's like when I think of kids reading Harry Potter," one of them says, and with that, the bros dissolve into fanboys.

In the end, the greatest risk doesn’t turn out to be any of the strangers that have occupied Moreno's backseat. That distinction goes to the increasingly carsick reporter riding shotgun. Moreno seems more concerned about me than her car. Before she takes any other calls, she points the pink mustache toward the highway to drive me home. I appreciate the gesture. It's what a friend would do.

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