Jason Sudeikis Reveals the Strategy He Used to Land a Date with Fiancée Olivia Wilde

How did Jason Sudeikis and Olivia Wilde meet? The Saturday Night Live alum told all on Monday's Late Show with Stephen Colbert

Jason Sudeikis knows that the best things in life are worth waiting for.

The 41-year-old actor stopped by The Late Show with Stephen Colbert on Monday, where he was asked how he was able to land fiancée Olivia Wilde — a beauty described by the late-night host to be out of his league.

“One of you is sooo attractive,” Colbert said. “You’re a funny guy and you’re a reasonably good-looking man. But she’s a different species.”

Sudeikis himself agreed. “Oh, it’s a different thing,” he said, listing all the physical ways in which his 33-year-old wife-to-be succeeds. “Bone structure, skin, teeth, eye color — literally just about everything.”

Olivia Wilde and Jason Sudeikis
Olivia Wilde and Jason Sudeikis. Jamie McCarthy/Getty Images

Olivia Wilde and Jason Sudeikis

So how did he do it? It all started when he was working at Saturday Night Live.

“I met her at a finale party for SNL,” Sudeikis said. “We hit it off that night.”

Romance, at the time, wasn’t in the cards — as Sudeikis had heard Wilde was dating someone else. Rather than be destroyed by that, he decided to play the long game.

“I actually came off looking a little cooler than I really am because I had heard through the grapevine, through mutual friends who weren’t exactly her best girlfriends, who would report back, ‘Oh you know, I think she’s dating someone,’ ” he explained. “So I didn’t make any moves. I was just very, very busy with other things. And next thing you know, I stopped being busy, she stopped dating someone, and then it was off to the races. ”

“We sort of reintroduced ourselves,” he added. “The universe had more in store for us in the fall.”

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While Sudeikis may have been playing coy, it turns out that Wilde wasn’t feeling so relaxed about his distance.

“I met Jason, and I thought he was so charming … but he didn’t even get my number,” Wilde told Allure in October 2013. “Over the next six months we kept running into each other. [One night], my best guy friend walked up to him and said, ‘This is Olivia’s number. Use it.’ That was the beginning.”

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Sudeikis and Wilde began dating in November of 2011. They have two children together — 2-year-old son Otis Alexander and daughter Daisy Josephine, born in October.

And though Sudeikis thinks Wilde is the attractive one in the couple, he did tell Colbert there is one area in which he has the advantage.

“I would say my penis is better. I’ll go on record saying I have a better penis,” he joked, then giving it a second thought. “Actually … we’re probably tied at best. She would just win because you’d be like, ‘Look at everything else!’ ”

The Late Show with Stephen Colbert airs weeknights (11:30 p.m. ET) on CBS.

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