Benson Boone Can't Stop Flipping + Surprise Cameo Leaves Us Speechless

Ranking the best months in NYC (00:00-9:39). Fran is loving Sterling Point (12:16-20:51). Jon Hamm & Anna Osceola are expecting their first child together (20:52-23:41). Benson Boone and the Jonas Brothers' flipping ability (23:42-42:31). Ria’s 25 day pilates challenge (44:47-51:51). We receive a surprise cameo that leaves us speechless (51:52-58:24). Beat Ria & Fran game 230 with Megan & Julia (58:56-1:22:03).

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