Possible Clues:

• The choice between courses of action, all equally undesirable
• Stupidly dim male may present a problem
• Hat raised to entitled female? That's a problem
• Plight of girl on back cover
• Predicament laid out over English military award
• Fix novel, after bending back cover
• Thorny situation
• Awkward situation upsets cover girl
• Turn over cover on novel -- Catch-22
• Cover up work of 22 across that's problematic