“Is that bothering you guys?” singer-songwriter Lucy Wainwright Roche, OC ’03, slyly asked in her feather-light voice, as she stood in red leather boots and tuning a guitar with a borrowed strap on the Cat in the Cream stage last Thursday. The audience laughed, and it was unclear when exactly she stopped talking and started singing: “Why not put all our doubts behind us / We’ve got Brooklyn at its finest.”

In celebration of the release of her sophomore album, There’s a Last Time for Everything, on Oct. 15, Roche drove to Oberlin from New York to play a reunion concert of sorts at her alma mater. “Pennsylvania, man. It’s too bad about that,” she said in a knowing voice after her first song, and already the audience was comfortable enough to return with a co-op knock. She seamlessly launched into a cover of Richard Shindell’s “The Next Best Western,” about driving to Ohio and listening to Christian radio, hoping God will keep you from falling asleep and driving into a truck on your way to a motel.

Before she experienced the trials and tribulations of Interstate 80, Lucy Wainwright Roche grew up in a family of musicians. Her parents are Suzzy Roche of The Roches and Grammy-winner Loudon Wainwright III, and her siblings Rufus and Martha Wainwright both have successful musical careers of their own. Growing up in Greenwich Village, Lucy considered herself something of a rebel, since she was the only one in her family who chose not to pursue music at a young age. However, after completing a creative writing degree at Oberlin, a master’s degree in education at the Bank Street College of Education and pursuing a teaching career in New York City, she went on tour as a backup singer with her brother Rufus Wainwright, and within two years had released a debut EP, 8 Songs in 2007. 8 More followed a year later, and in 2010 she released her first full-length album, Lucy.

Now Brooklyn-based, Roche has been compared to Joni Mitchell and has played with Neko Case, the Indigo Girls, Girlyman, Dar Williams and Amos Lee. On her last album, she collaborated with This American Life’s Ira Glass on a cover of Elliot Smith’s “Say Yes.” She won the Falcon Ridge Folk Festival’s “Emerging Artist” competition in 2008, and a year later the Grassy Hill Kerville Folk Festival’s “New Folk Singer-Songwriter Competition.” Though she eventually followed in her family’s footsteps career-wise, she’s developed a uniquely sweet and serious folk sound. Her forthcoming album will be the first full-length album in her eight-year career without any contribution from her family members.

Roche might have left her creative writing degree and teaching career behind in favor of music, but the poetry in her music is Dylan-esque, with lyrics like “My love, my love, are you on a winter beach tonight? / Waiting on a last chance rocket ride over the boardwalk?” from “Open Season.” During shows, she says what’s on her mind, plays some beautiful music — from her originals to Beatles covers to Train’s “Hey, Soul Sister” — and doesn’t take any of it too seriously. Her songs revolve around life on the road, beautiful people in beautiful places, the nature of memory and reflection, loving someone who’s wrong for you (“That song was written about an Oberlin grad,” she giggled after “The Worst Part”) and “rocking numbers” that she turns into “sad snoozers,” like “Call Your Girlfriend.”

The sweetest part of the show was how at home Roche felt here. As an alumna, she has a personal connection to this place. When asked why she came back to Oberlin, she said she loves playing here; the audience is always “interesting,” and she worked at the Cat herself as a student. She wanted to play her music, but as much as that, she wanted to chat, catch up, see what’s changed and sing with us. “I’ve been driving alone for five years!” she exclaimed in dismay when she noticed the audience was a little shyer than she remembered. Her openness was disarming, and when the audience loosened up, there was a palpable connection to be felt. She talked about the first time she played at Oberlin (the first-year talent show, a song about babysitting); the craziest thing she ever did here (kept two cats in Langston Hall her sophomore year; the fire safety report simply said “two cats were observed”); what she listened to on her way here (“It’ll All Work Out” by Tom Petty and Miley Cyrus’s “Wrecking Ball,” which she wants to cover).

Near the end of the show, she called her dog, Maybe, up on stage, and put it right to sleep while everyone sang along to “Wild Mountain Thyme” by Francis McPeake. Upon request, she played “Snare Drum,” which she described as an “Ohio song,” it won her an Independent Music Award for Best Folk/Singer-Songwriter Song in 2009.

Afterward, audience members commented that there was something full and therapeutic about hearing her voice. Perhaps seeing their Oberlin experience mirrored in hers reminded them how calling a certain town in Ohio home for four years can take on far more meaning in retrospect than one attributes to it when they’re still in the midst of the experience.