When Timothy Russo decided to propose to his girlfriend, Jana Rugan in 2008, he knew he wanted to make it special, but he never imagined it would also become a scene in Rugan's favorite show, "How I Met Your Mother." His original plan was to take Rugan to a taping of the show, and propose to her on a Santa Monica beach as they watched the sunset. But Russo's brother, a Los Angeles-based comedy writer, came up with a different plan. "Do you want to propose on the show instead?" Russo remembered, telling the New York Daily News how it came about. "I couldn't believe it, I was, like, 'What do you mean?' He said in the season finale, they were writing in a proposal, and had planned to use extras, so thought what a great chance to do it for real."
In Season 2, Episode 22 ("Something Blue"), Ted and Robin tell Barney (Neil Patrick Harris) the story of their breakup, and how it began at a restaurant when Robin discovered a ring in her champagne glass and freaked out, thinking Ted was proposing. Rugan and Russo were extras in the background, but after the director shouted a secret signal, Russo got down on his knees and proposed to a shocked and ecstatic Rugan. "At first she thought I was messing up the scene, then it dawned on her and she started crying and everyone was clapping," Russo recalled. "It was awesome." Fans obviously agreed, with the "How I Met Your Mother" Season 2 finale making it onto several best episode lists.