The Osbornes arrived in New York City on Friday, May 11 and checked into The Time Hotel, which Diane described as "a fantastic hotel in a perfect location!" They had dinner at the elegant midtown seafood favorite Oceana that night, then saw the Tony Award-winning Broadway musical Jersey Boys at the August Wilson Theatre. Said Diane Osborne: "Jersey Boys was an absolute blast! We had so much fun!"

On Saturday, the mother-daughter team had dinner at the classic restaurant & bar, Hurley's prior to seeing the Off Broadway show, A Jew Grows in Brooklyn at the Jaqueline Kennedy Onassis Theater, which Michele Osborne described as "wonderfully moving and funny!"