Ever want to ask out Taylor Swift?

Duncan Penn of The Buried Life had the chance to do just that -- and he's taking viewers behind the scenes of the big moment on Monday's episode of the MTV reality series.

"We try to ask her out with a crazy plan that involved hundreds of fans and a fake country singer," costar Jonnie Penn tells UsMagazine.com of the ask, which happened at the 2010 CMT Awards in Nashville. (Watch the video, above)

Now that they've managed to cross a date with Swift off their list of things to do before they die, the boys are ready to befriend another A-lister: Robert Pattinson. "It was the strangest thing we've ever done," Duncan says of his interaction with the star as part of a dare, to be seen on an upcoming episode. "He is a tough guy to track down!"

Check out the clip above for Duncan and Jonnie's must-see moments and tune in to The Buried Life at 10:30 p.m./ET on MTV.

By Allison Corneau for UsMagazine.com. For more Channel Surfing, click here.