Ben Stiller portrays risk-averse Reuben Feffer, whose best-laid plans for life and love zoom wildly off track when his wife (Debra Messing) dumps him on their honeymoon for a scuba instructor (Hank Azaria). Stunned, humiliated and in the grip of acute indigestion, Reuben plans to play it safer than ever. But a chance encounter with an adventure-craving, globe trotting friend from middle school (Jennifer Aniston) shoots him into a whirlwind of extreme sports, spicy foods, ferrets, salsa dancing and living in the moment.