Long before Tinder, dating was a complicated mix of happenstance connections, missed phone calls, and the ever-important rules for dates one through five. Add in the baggage that comes from dating in your 30s and 40s — namely, exes and kids — and nerves are at an all-time high. This is the premise of the aptly named Fifth Date by Lori Boyd, now offered by DC’s Nu Sass Productions. A heartwarming ride through attraction and the not-so-quiet voices of anxiety whispering in your ear, this world premiere proves that jumping in with both feet is worth the risk.
Newly acquainted and still awkward, Jil and Ted navigate an all-important fifth date with wine and lasagna. Not quite casual but also not quite serious, it’s the date where things could go either way, and with omnipresent play-by-play commentary, their invisible alter egos work tirelessly to ensure they never forget that. Add in the pre-Y2K vibes of track lighting, answering machines, and Nokia ringtones, this one-act romcom energetically explores what happens when your inner and outer thoughts trip over each other through an evening of romance and vulnerability.

Back out into the dating world for the first time after a hard divorce, Jil, played by Rebecca Ellis, wavers between reaching for a genuine connection and retreating due to her insecurity. As an actress experiencing a streak of bad luck just as her body decides to remind her just how old she’s becoming, Ellis’ Jil exudes a tense and tired outlook on life while also balancing an unshakeably hopeful wish for love.
Ted, played by Steve Lebens, also hopes that tonight is the date to take things from an intellectual connection to a deeper emotional (or physical!) level. A fifth-grade teacher with a penchant for alphabetization and ironing, Lebens’ Ted is earnest and eager and navigates the story’s events with bright eyes and a warm smile.
Hanging over the shoulders, quite literally, of the story’s hopeful lovebirds were Jil’s Alter Ego, played by Aubri O’Connor, and Ted’s Alter Ego, played by Terry Heffernan. A steady pulse of absurdity and one-upmanship, this delightful duo settled into a groove as the wine began to flow for their corporeal selves. Heffernan’s Alter Ted kept his energy revved up to 11 pretty much the entire time with a mischievous grin and perpetually arched eyebrow. O’Connor’s Alter Jil delivered enough delightfully witty and casual one-liners to steal the show. Really finding their rhythm together in the latter half, many of my favorite parts of the production came from the Alter Egos’ bickering set against (or sometimes on top of) Jil and Ted’s fifth date on the couch below.

In a space nestled among the office buildings of Metro Center DC, the creative team at Nu Sass Productions carefully crafted a time capsule Fifth Date world where love is possible even when cellphone service is not. Direction by Lynn Sharp Spears kept a steady flow of energy moving around and through the actors on set, while Intimacy Coordinator Ian Claar grounded the fireworks. Set design by Shiloh Coleman and prop design by Rye Ellis transported you, CD tower and all, back to the 1990s, accented easily by Stephanie Yee’s costume design. Lighting design by Chris Muska cleverly carved out an altered state for the Alter Egos, which they called the Void, amid the normal-life apartment, while sound design by Kathryn Parr made sure we never forgot what decade we were really in.
With this charming flashback of a romcom playing through the middle of November, Nu Sass Productions offers a refreshing and often silly escape from the current stressors of our larger world. Filled with heart and bravery, Fifth Date is a step back in time to the wholesome, quirky loves of the ’90s and ’00s, giving us all something to smile at, laugh about, and cheer for, which, in my book, makes for a pretty successful fifth date.
Running Time: 90 minutes.
Fifth Date plays through November 15, 2025, presented by Nu Sass Productions, performing at the Nu Sass Theatre located at 1100 H St. NW, Washington, DC. Tickets run. For tickets ( PWYW-$25), purchase them online.
Fifth Date
Written by Lori Boyd
Directed by Lynn Sharp Spears
STARRING
Rebecca Ellis: Jil
Steve Leben: Ted
Aubri O’Connor: Jil’s Alter Ego
Terry Heffernan: Ted’s Alter Ego
Jessa Whitley-Hill: Jil Understudy
Mark Mumm: Ted Understudy
Natalia Fyfe: Jil’s Alter Ego Understudy
Josh Poole: Ted’s Alter Ego Understudy
CREATIVE TEAM
Artistic Director: Aubri O’Connor
Producer: Elle Sullivan
Production Manager: Ileana Blustein
Stage Manager: Sara Karako
ASM: Danielle Carter
Light Designer: Chris Muska
Sound Designer: Kathryn Parr
Set Designer: Shiloh Coleman
Costume Designer: Stephenie Yee
Intimacy Coordinator: Ian Claar
Props Designer: Rye Ellis
House Manager: Joe Largess
Marketing: Hannah Wing-Bonica


