Time and time again, The Office’s Michael Scott put it all on the line in pursuit of a woman to settle down with, navigating his way through all hilarious levels of inappropriateness, over-investment, self-destruction, and lack of self-awareness. Armed with awful judgement but perpetual sincerity, Michael stayed true to his domestic dream and continued to follow his less-than logical heart. After seven rocky seasons, it finally payed off, but not before taking him on quite the awkward ride.