Leonard found Penny saying good night to Doug when he tried to return her mail. Doug asked Leonard how he was and called him "bro" which Leonard returned. During Leonard's misunderstood date with Penny she told him about Doug. He was a quick fling of 36 hours of guilt ridden sex she had while still getting over her former live-in boyfriend Kurt.
Doug was deeply distraught after the break up. Shortly after things ended with Penny, Doug moved to Wisconsin to continue on his family's legacy of cheese cultivation and production. Initially struggling with the demanding labor required to become a cheese-monger, Doug eventually found his way and opened the Mid-Western Artisan Dairy Lounge.
While Doug appears on the surface as a brash and uncaring person, he is truly a kindhearted and devoted person. When his business fell upon hard times in Wisconsin, he continued to work tirelessly to keep his cheese fresh and up to standards and his employees happy.
Doug eventually fell in love with a man named Ronald Benson, who owned a coffee shop in Milwaukee. The pair were married several years into their relationship and had 3 children, Amadeus, Quinn, and Rachel. Ron continued to run his coffee shop, which grew considerably over many years and Doug expanded his cheese making empire to stretch into several prominent mid western cities including Chicago. Doug moved the family closer to the city of Milwaukee into a two story contemporary house next to a lake. Currently Doug works to merge the two business he and Ron have into a coffee and cheese artisan company.