A dinner between Editor-in-Chief of the Daily Caller Tucker Carlson and Bill Ayers, a former domestic terrorist, could make for a very awkward evening. So much so, we like the idea.

Carlson actually won a dinner with Ayers on Friday for donating $2,500 to the Illinois Humanities Council, according to the Chicago Tribune. “I bought the auction dinner because I support the important work of the Illinois Humanities Council,” Carlson said in an email to the Tribune. “Anything I can do to help.” Sounds like a hint of sarcasm.

The Humanities Council is a nonprofit that “promotes greater understanding of, appreciation for, and involvement in the humanities by all Illinoisans, regardless of their economic resources, cultural background, or geographic location,” says their website.

Ayers is a retired professor of the University of Illinois at Chicago and was negatively associated with President Obama throughout the 2008 election. The pair served on the board of a nonprofit organization from the  mid 1990s to early 2000s.

The dinner is set to include six people and will happen sometime before October 2012.