2. Michael and Holly
Total Score Average: 4.6
"My resolution? I never want to make Holly cry again. Unless it's from laughing too hard. Or making love too beautifully." - Michael Scott
Michael and Jan may have had that whole strange opposites-attract vibe, and there was some definite chemistry there at the peak of that relationship, not to mention humor. But in the end, Michael and Holly's relationship was not only Michael's best romance, but one of the best romances in the series. Holly Flax was a character designed for Michael. Smart, beautiful and sweet, she also somehow managed to grasp his sense of humor. She found his awkwardness endearing in a way that few women could. The two were funny together, they were irresistible on screen and they proved to be made for one another, though it took some time to make it happen. After a brief romance, a break-up and a reunion, the two ended up getting engaged and moving off to Colorado together. Living happily ever after, they are.