Zach Galifianakis is back with his latest sit down interview on Between Two Ferns. This time he gets really awkward (and hilarious) with Brad Pitt, asking him about Jennifer Aniston among other things.

“How old were you when you lost your virginity, zero?” asks Galifianakis before almost beginning to speak about his own experience. Pitt stops him before things get too awkward.

Galifianakis also makes things very awkward between the two when he asks Pitt the question “Tell me what it was like the first time you laid eyes on Angelina. Was it like one of those classical love stories? Like when, I don’t know, when Ross first saw Rachel? You know that show Friends, have you seen it?”

Watch the hilariousness below:

Galifianakis has made a hit out of these random episodes of Between Two Ferns landing hilarious and buzzworthy episodes with U.S. President Barack Obama and the infamous Justin Bieber. Fans loved the Bieber video mainly because Galifianakis sort of verbalizes what most people have been thinking about Bieber for the last several years. Catch both of those episodes below as well.

Pitt was likely promoting his latest film Fury which the out-of-touch character of Galifianakis refers to as “Furry.”

How does this episode of Between Two Ferns stack up against the others?