In love, sometimes everything looks good on paper, but the chemistry just isn't there and things don't quite click. In theater, the same can be true, and seems to be the case for Gary Lennon's update of his 1995 play Dates and Nuts, which explores the pitfalls of the dating game in New York City.

Eve (the always funny Elizabeth Regen) and her best friend Mary (a charming Dianna Aguilar) begin the play parked on Eve's Brooklyn stoop, ogling men who pass by. Eve has a rough bravado to her sexuality, claiming that she's “definitely an ass woman.” But somewhat prototypically, that tough exterior papers over her insecurity about her breakup with her ex-boyfriend, who turned out to be gay, or “G” as she puts it. Lennon cleverly crafts a scene that inverts the usual paradigm of men ogling female passersby.]

The laughs truly step up, on leopard print heels, when Patrick (Darryl Stephens), Eve's drag-queen neighbor passes by and accosts Eve about a tacitly homophobic remark. Again, Lennon slyly employs humor to tackle an all-too-common problem. And even if Patrick veers into the “sassy black friend” stereotype at times, Stephens is hilarious as he “preaches” to the ladies about life and love in rhyming aphorisms. His character, added in the play's update, may be the funniest part of the show.

Darryl Stephens as Patrick; Credit: Courtesy Bootleg Theater

Darryl Stephens as Patrick; Credit: Courtesy Bootleg Theater

As Eve goes on a quest for sex and love, she comes across annoying pickup artist Donald (Dave Scotti), who is obsessed with mentioning his penchant for cooking, and potential soul mate Al (Josh Randall), who is mildly reminiscent of Sex and The City's Aiden Shaw, in the same bar on the same night. Things progress between Eve and Al, but not without complications, some of which are a tad predictable.

Despite the collective credits and talents of Lennon, his director Wilson Milan (Tony-nominated for Lieutenant of Inishmore) and his leading lady Regen, the romantic comedy doesn't land emotionally, making it difficult to invest in the characters outside of their laugh lines. Milan's direction darts from comedy to anger to pathos without a finesse that would make such transitions credible.

And speaking of transitions, the ones between scenes take far too long, even if Lennon and Milan cleverly employ Donald's character to hit on the stagehands. Stephen Gifford's set is pedestrian, especially when compared to his other excellent work.

And there's just far too little of Patrick on stage.

Bootleg Theater, 2220 Beverly Blvd., Westlake; through July 13. (213) 389-3856. www.bootlegtheater.org.

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