Jackie Joseph is using her married name for the character name. She was married to singer / actor Ken Berry from 1960 to 1976.
Craig imitates Sinatra's performance style, but Lucy jokingly says she thought he was imitating Lawrence Welk. Lucy admits that Sinatra was her idol when she was a teenager. Lawrence Welk will play himself on a 1970 "Here's Lucy".
Kim and Alan are going to the drive-in to see a (fictional) Italian film titled 'La Notte Del Bacio Dolce', which translates to 'Sweet Night Kiss.' Craig also goes on a date to another drive-in with his girlfriend Patty. This may be a reference to Desi Aranz Jr.'s dating Patty Duke, although most sources agree that the two did not meet until 1970, after this episode was filmed.
Lucy does a long comic take when she realizes Kim and Alan are going to a drive-in. In the 1950s and 60s drive-in movies were dubbed "passion pits" because they were a popular place for teenagers to be alone together for making out on a date. The fourth drive-in theatre in the nation was in located Los Angeles and opened in 1934.
Harry is home alone ogling the centerfold of a magazine that has a scantily clad woman on the cover. Although the magazine's name has been taped over, it is likely supposed to be Playboy magazine. In the style of Playboy's founder, Hugh Hefner, Harry wears a red silk smoking jacket and is drinking a cocktail.