Seeing Village Repertory Theatre’s production of Daddy Long Legs at Woolfe Street Playhouse gave me the sensation of tucking into a rambling Victorian novel on a blustery night. That’s not just because this two-hander, ballad-happy musical teams up director and writer John Caird (Les Miserables co-director) and composer Paul Gordon (Jane Eyre) to cozy up to that famously fusty era. And it’s not only because it’s based on the 1912 novel written by Jean Webster, who happens to be the grand niece of Mark Twain.

There are also plenty of other components of this production, which is directed by Keely Enright, conjuring a bygone time. There are lugubrious, mahogany-esque library surroundings. There are prim layers of embroidered garments and starchy suits. More to the point, however, is that this work firmly fixes itself in earlier days by taking its own sweet, wordy, winsome time.

Like a luxuriant, purple-prose novel, during which boy and girl just overcome all manner of missteps and misunderstandings, Daddy Long Legs leisurely unfolds its tale, meting out ballad after soulful ballad to recount the college years of a plucky female orphan named Jerusha Abbott, a quirky benefactor called Jervis Pendleton who is cloaked in anonymity, some related hoity-toity New York heirs, and a veritable tome of correspondence.

The oldest ward at the John Grier Home, the clever, creative Jerusha is rescued from a life of certain servitude when a trustee, the youngish, loaded, and preternaturally serious Jervis, takes note of her witty essay and elects to fund her college studies. His stipulation is that Jerusha must write him daily to thus refine her writing skills. All she knows of his identity is the glimpse of his long-legged shadow at the orphanage during a trustees meeting. So Jerusha amiably dreams up her own likeness — a kindly octogenarian she crowns “Daddy Long Legs.”

What ensues for the following two and half hours is a sweet-natured succession of Jerusha’s letters, set to rolling, resplendent song. These are sung both by Jerusha as she writes them and by Jervis as he reads them, spanning the full four years of college, including summer breaks. It gets tricky when Jervis grows ever fonder of his beneficiary, while Jerusha gains a confidence that sometimes runs afoul of her benefactor’s ardor.

Trickier still is the work’s premise that Jerusha has fashioned her anonymous donor into a father or perhaps grandfather figure, particularly when his hots for her play out in controlling mandates. Sure, there is the redemptive, politically correct through line of Jerusha asserting herself in the face of his edicts. Still, it’s hard not to squirm under Jerusha’s cooing “Daddy” salutations in today’s #MeToo moment, as his desire and his purse strings clash and command in ways unsettling to our contemporary sensibilities.

The music does much to defang this central head-scratcher, washing over the audience by way of the pleasant, proficient pipes of Lara Allred as Jerusha and Aaron Andrews as Jervis. Under the able musical direction of Anne Warf, who is on piano accompanied by Charmaine LeClair on cello and Matthew Walker on guitar, Allred and Andrews rally agreeably through the show’s sizable song list of 25 numbers, no small feat to be sure.

Both performers are easy on the psyches, too. Allred is a charmer, a bright-eyed, sympathetic Jerusha who is thoroughly convincing as an impressionable orphan who grows with her newfound knowledge. Andrews plays it straight as Jervis, befitting of the importance of being earnest in that era, grappling to great effect with his increasing love-lorn torment, though with less of the eccentricity that bemuses Jerusha.

Then there are the sumptuous set and costumes. The former bridges the Woolfe Street Playhouse walls with a raised, book-lined library for Jervis, while Jerusha’s floor space thrusts out, surrounded on three sides by the audience. Jerusha styles an early 20th century hit parade of fetching tops and fitted floor-length skirts, and Jervis is suited accordingly.

It is through these fine trappings, but mostly through the transporting power of song, that we are nestled in for a night at the theater. As much as a theater seat allows, we curl up in an august library, immersed in the correspondence of star-crossed lovers of another time, when power dynamics of daddies and daughter were an altogether different construct. Yet now as then, those times were begging for a clever comeuppance from the freshly educated and now fiercely independent Jerusha Abbott.

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