Possible Clues:

• Tart about the novice being smoother
• Home club will get even!
• Press agent offering old-fashioned evening out?
• Pre-electric clothes presser
• Building south of Madison Square
• Old domestic implement novice plunged into tart
• ___ Building (N.Y.C. landmark designed by Daniel H. Burnham)
• Beginner's tart casing that was hot and heavy
• __ Building: Manhattan landmark named for its triangular shape
• Hair-straightening device