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Donald Trump on The Late Show with Stephen Colbert is guaranteed to be awkward

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It was only a matter of time: Donald Trump has accepted Stephen Colbert’s invitation to appear on The Late Show. When the two sit down together on Tuesday, Sept. 22, it’s bound to be a strange conversation. Given that Trump doesn’t have a history of responding well to criticism and Colbert dedicated a segment of his inaugural episode to ridiculous Trump storylines (and an Oreo binge), it’s fair to say that things could get uncomfortable.

While stuffing his face with cookies on the Sept. 8 show, Colbert made light of everything from Trump’s comments about building a wall between the U.S. and Mexico to his appearance. He did exercise restraint for at least a moment, though, calling Trump “the most whatever-it-is of all time,” rather than inserting a more telling noun. It’ll be interesting to see how Colbert handles having the wildly controversial politician in front of him. Will the Late Show host be as friendly to Trump as he was to Jeb Bush, or will he return to the tactics he used with guests on The Colbert Report?

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Colbert’s interview with Bush was tame, and the two treated each other politely. Of course, Trump hasn’t always been known to play nice; he’s responded aggressively to political commentators on more than one occasion (just ask Megyn Kelly). Plus, he’s likely seen the clip of Colbert mocking him and may be feeling defensive coming into the interview.

Just what convinced Trump to appear on the show is unclear. Perhaps he wanted a chance to respond to the host, or maybe he was swayed by the premiere’s impressive ratings. After all, The Late Show with Stephen Colbert averaged 6.55 million viewers on its first night, which was substantially more than its competition from The Tonight Show Starring Jimmy Fallon and Jimmy Kimmel Live. There was a drop in viewership for the second episode, but 3.657 million people still tuned in.

Before his appearance on The Late Show, Trump has an interview on the The Tonight Show scheduled for Sept. 11. Meanwhile, Colbert will be interviewing several other political figures, including presidential hopefuls Sen. Bernie Sanders on Sept. 18 and Sen. Ted Cruz on Sept. 21.

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