Caroline and Max meet Sophie's new boyfriend, who gives them big tips and is a bookie at the track. When he invites the girls to join him and Sophie at the track for a day of fun, they have the time of their lives after turning their $200 tips into $600. But the gambling bug bites Caroline hard and soon she has lost all their money and owes Nicky $3,000.
With no hope of getting the cash, Nicky offers a trade: Chestnut in exchange for what they owe. Distraught over the thought of losing her beloved horse, Caroline doesn't know what to do. Luckily Earl pulls himself out of gambling "retirement" and saves the day by helping them win back the exact amount they need. With that, Caroline's gambling days are over.