On Thursday, viewers will say goodbye (and probably one or two final "that's what she saids") to Steve Carell as he prepares to exit The Office. But how did we get here? Since the first season, all Michael Scott has ever wanted was to get married and reproduce ("100 kids" so he would have "100 friends," to be exact), but there were times when most fans — and most of his co-workers — didn't think he'd have such a happy ending. As Michael prepares to run off into the Colorado sunset with fiancée Holly and into Dunder Mifflin's history books, we look back at how TV's most embarrassing boss went from Prison Mike (and Date Mike and Agent Michael Scarn) to soon-to-be family man.
Michael's New Pad: Michael buys a condo and meets future girlfriend, his real estate agent and (almost future fiancée) Carol. On the downside, he will spend the next 30 years paying for the property, but on the upside, Jim awards him with the gold yogurt lid/medal for his purchase. (Oct. 4, 2005)
Michael and Jan's First Kiss: Michael and Jan share their first kiss (and then go to second base at a local hotel) after he successfully wins over a big client with Chili's apple blossoms and margaritas. While out on business, the rest of the office finally finds out about Agent Michael Scarn and Michael's secret script. (Nov. 8, 2005)
Michael's Two Dates: Michael accidentally asks both Carol and Jan to casino night, but can't bear to break it off with either woman. He begins dating Carol and Jan returns to New York that night, alone, with her overnight bag (oops!). (May 11, 2006)
The First Proposal: Caught up in the moment at a Diwali celebration and inspired by Kelly's parents, Michael proposes to Carol (while she is in a cheerleading costume no less), and she surprisingly says no. The two later split when he superimposes his head over her ex-husband's body in a family photo. (Nov. 2, 2006)
Full Disclosure: Michael accidentally sends a picture of him and Jan together on vacation in Jamaica to the entire company, which forces them to come out publicly. He later breaks up with her at the urging of his female employees, but gets back together with Jan after she gets breast implants. (Jan. 4, 2007)
The Last Straw: After months of supporting Jan and her new candle-making company, Michael and she get into a huge fight in front of their friends at a dinner party. The night ends with Jan breaking Michael's beloved Dundie award, and Michael leaving Jan. (April 10, 2008)
Love at First Sight: Michael scores twice when Toby leaves Dunder Mifflin, and he falls hard for his replacement, Holly. The two kindred spirits quickly begin dating, but Holly is transferred to New Hampshire as soon as corporate finds out and the two split because of the distance. (Sept. 25, 2008)
The Michael Scott Paper Company: Nobody cancels a Dunder Mifflin party on Michael, especially when it's his 15th anniversary party. In response, Michael does the unthinkable and leaves Dunder Mifflin. He soon starts a rival business and recruits Pam and Ryan, still recovering from his corporate scandal, to join him. (March 19, 2009)
Wedding Fever: Love is in the air at Jim and Pam's wedding, and Michael ends up spending the night with Pam's mom, Helene. The two start a relationship, but when he learns her real age on her birthday, he breaks things off. To add injury to insult, Michael later gets slapped by Pam, who had told him not to date her mom in the first place. (Oct. 8, 2009)
The One: After failing to tell Holly he loves her at the company picnic the year before, Michael reaches out to new company owner Jo and asks her to transfer Holly back to Scranton. He later again realizes his strong feelings for her when he is forced to call her and tell her to get checked for Herpes. (May 20, 2010)
The Second Proposal: Although she originally transfers to Scranton still dating longtime boyfriend A.J., Holly is later convinced to break up with him because of his lack of commitment. She and Michael soon start dating, and, when Holly tells him she must move to Colorado to care for her parents, he proposes to her under the office sprinklers and announces to the staff his impending departure. (March 24, 2011)
The Office airs Thursday at 9/8c on NBC.