By Elysa Gardner, USA TODAY July 13, 2010 NEW YORK — Harry Connick Jr. recently came up with the perfect analogy to describe how he builds a relationship with a live audience: "I decided that it's a lot like going on a date." Connick, 42, who has been married for 16 years, concedes that he hasn't dated anyone "in a really long time — and I'm glad about that, because I wasn't any good at it." But the prolific singer/actor/musician/composer — who on Thursday launches Harry Connick Jr. in Concert on Broadway, a two-week engagement at the Neil Simon Theatre — says the metaphor readily applies to putting on a show. "You prepare for a date, get dressed and ready, but you never know what the conversation will be like," says Connick, chatting in a dressing room at The View. "I think the evening's success depends a lot on whether you're a good listener." Similarly, Connick, since making his name as a piano-playing prodigy in the 1980s, has aimed to cater to fans night by night. "Sometimes you try a song and people don't respond, or you tell a story and you just hear crickets," he says. "But when you play thousands of shows, you start to refine stuff." Connick has seduced Broadway crowds before, in 1990's An Evening With Harry Connick Jr. and His Orchestra, then in his Tony-nominated turn in a 2006 revival of The Pajama Game. (He earned another Tony nomination for writing the score for the 2001 musical Thou Shalt Not.) In Concert will be less structured. Though technically it's an extended stop on his tour promoting last year's Your Songs, a collection of standards, Connick says, "this is special, because it's a Broadway house, so I'm writing some new stuff. And the way I perform, things are always a little different. It would kill me if anyone who saw this show twice saw the exact same thing." Playbill editor Blake Ross expects that Connick's combination of restless virtuosity and mass appeal will prove the perfect tonic for a typically sleepy Broadway summer. "He's got that matinee-idol quality that appeals to traditional theatergoers, where younger audiences know him from movies and TV and the millions of records he's sold." Connick's future plans include a new stage musical he's composing and will appear in. He'd also love to do a film musical. For now, though, In Concert will be his preoccupying challenge. "There's pressure to do something new every night," Connick says. "But I like that. I have a short attention span ."