The single singer isn't single anymore.

We may be starting this story at the end, but that's the most gratifying part about Karen Gross' five-year-old cabaret show, Sex & the Single Singer.

During her performances, Gross has sung songs and cracked jokes about dating in front of sold-out audiences at Old City's Tin Angel bar. But over the years, she somehow settled into herself, and now she says she has worked through her meshugas.

The 31-year-old singer-by-night, marketer-by-day is cohabiting with Dan Creskoff, her boyfriend of two years. He will even join her on stage for the five-year-anniversary performance Friday night at the Ruba Club. (The Tin Angel just wasn't big enough for this party.)

"I'm not single anymore, but the journey still happened," said Gross as the couple's 5-month-old kitten Vinnie scrambled across the hardwood floors in her Center City apartment. Creskoff beamed as Gross chattered. "But I'm in a new chapter, and I want my show to be reflective of it."

With a voice as clear as Karen Carpenter's and the looks of Anne Hathaway (full lips, to boot), Gross and her cabaret show have gained a local cult following, partly because - thanks to Sex and the City - it was hip to lament the singleton's challenges. Gross is also well known among the city's hard-to-distinguish publicist/freelance-writer crowd.

Sex & the Single Singer, performed about four times a year, is part comedy, part melancholy, and very autobiographical, considering that Gross wrote the show at 26 when she was fresh off a breakup. The play - which debuted at New Hope's then-hot spot Odette's - embodies the feeling of longing for Mr. Right. And like most single women, it is moody.

One minute Gross, who always performs with full red lips and a cocktail dress, is singing a down-in-the-dumps ballad; the next she's making fun of herself (one of her top 10 dating disasters was when her date said she reminded him of his mother). And then she's singing about hope. Who hasn't been there?

But the show is always changing, as Gross incorporates current affairs into the performances. In earlier shows, Jessica Simpson and Nick Lachey's breakup was a topic. Now she pokes fun at dating during the recession. "No one is going to the fancy-shmancy pickup joints like Rouge," she says, laughing. "Instead they are cruising the aisles at Trader Joe's."

Throughout the performance, Gross transforms herself into characters familiar to every single girl. First she's the bridesmaid - she dons a dress from her own collection. She's also the nosy but well-meaning, happily married pregnant friend; a gynecologist named Dr. Connie Lingus; and concerned grandmother Lois Ginsburg.

"After my first show, that was the one people were really excited about," Gross said. "Everyone relates to her."

While she has enjoyed success, Gross is by no means ready to give up her day job as director of sales, marketing, and public relations for City Food Tours.

She did land a 2006 gig singing Irving Berlin songs at Lincoln Center in conjunction with the release of the book Irving Berlin's Show Business, by Bucks County author David Leopold.

And from time to time, Gross performs at private events. She once did a personalized rendition of Sex & the Single Singer for a bachelorette party. She's also working on some recordings that she hopes will one day become her second album. WXPN-FM (88.5) plays songs from her first, called Navigating.

Friday's performance will feature an original song by Creskoff, as well as 10-minute riffs on being single by local comedians Jennifer Blaine, Jess Carpenter, and Dave Terruso.

"The show has grown so much," said Blaine, who helped Gross perfect her comedic routines early on. "I'm surprised every time I see it. Some of it is really deep, and some of it is really funny. I'm so proud of her."

Gross grew up in Doylestown with a mother who was in the food business and a physician father. She graduated with a degree in American studies from Wesleyan University and returned to Bucks County to work at the New Hope Gazette newspaper, eventually becoming an editor at the Bucks County Herald. All the while, she was singing.

In 2005, when Gross was working as a contributing writer for Philadelphia Magazine, Bob Egan, Odette's producer, was frequenting her mother's frozen yogurt store, Thinny Delites. Barbara Gross would talk about her daughter's singing aspirations. Eventually, Egan asked her to come in for an audition.

"She was really lovely," Egan said. "She sang a few songs that she wrote and a song by Carole King, I think, and I liked them. So I started putting her in my Monday night showcases."

Two years later, Egan offered Gross the honor of performing in her own one-woman cabaret. That was when she was inspired to write Sex & the Single Singer.

"Up until then, I was doing the singer/songwriter circuit, more like coffeehouses," Gross said. "I realized I had all this funny material in my journal about being single, so I decided to create a whole new concept. It's changed my life."

Contact staff writer Elizabeth Wellington at 215-854-2704 or ewellington@phillynews.com.