Jon Hamm and Anna Osceola's relationship timeline as they get engaged

The show Mad Men changed 's life in many ways. Not only did it propel him into the spotlight and help launch a major career for the actor, but it also brought his future-wife into his life.

Jon, 51, met Anna Osceolo, 34, eight years ago when she appeared in one episode of the popular AMC show as a receptionist.

When their paths first crossed, Jon was in a loving relationship with actress Jennifer Westfeldt - but just months after he met Anna, news hit the web that he and Jennifer had split after a whopping 18 years together.

Load More