Possible Clues:

• Perhaps playboy later rued playing around
• Who later rued straying?
• Playboy's admired until the rapture ends, right?
• Member of union that's moonlighting?
• Has grown up with a couple of Cockney girls, now married and still chasing around
• Certain commandment breaker
• Durer tale (anag)
• Hester Prynne of 'The Scarlet Letter,' e.g
• Repeated hesitation by mature person to become unfaithful type
• One's business affairs?