Duckie Dated Demi, and Ashton Stole Eastwood’s Girl

by Hollee Actman Becker
Originally Published: 

Last night Jon Cryer and Scott Eastwood were in the house. And TBH I wasn’t really feeling it at first. For starters, I’ve never been a huge Jon Cryer fan. And Scott Eastwood? I literally had no idea who he was. Turns out, Clint’s his dad. Yawn.

You know who was feeling it? Andy Cohen. The show kicked off with him telling Scott that he had to unfollow him on Instagram because he was getting too turned on. Um…awkward! But then cue up the montage of Scott’s shirtless selfies, and trust me when I tell you that every woman in America now knows who this kid and his hot naked torso are.

Next up: a game of “Would It Give You Wood, Eastwood?” in which we find out that Scott doesn’t like breast implants, he’s kind of into cougars, and his cutoff age for dating a chick is 45. Which gives me about three months.

Meanwhile, Andy is now whipping out accessories from some secret place behind his chair for a live re-enactment of the infamous nightclub scene from Pretty in Pink. Jon reprises his role of Duckie, Scott plays Blaine, and Andy takes over for well, Andie, complete with a floppy red Molly Ringwald wig that makes him looks nothing at all like Molly. His eye rolling game is on point though.

Now here’s where things really start to get interesting. Because after the Tony-worthy performance, Will from South Dakota phones in to ask Jon if it was awkward when Ashton Kutcher joined Two and a Half Men since they both dated Demi. Cryer gives a little self-deprecating laugh—wait, is he blushing?—and admits that yes, it was a little awkward, yes the two men discussed it, but no, they never went into details. Case closed. That is, until Scott leans in to place his hand on Jon’s shoulder and drop this awesome little bit of intel: “If it makes you feel any better,” he says, “he did sleep with one of my ex-girlfriends.”

Shit just got real, people!

But wait…there’s more! Because apparently Ashton’s douchebag move was the catalyst for his breakup with Demi! You heard me. Now do you see why I want Andy’s job? And we’re not even done yet. As a coda, Dorothy calls in, not from Kansas, sadly, but from California, to ask Jon what his favorite Two and a Half Men episode was. The only obvious answer being: The one with the threesome where he got to repeatedly lick Courtney Thorne-Smith. Um, ew.

This naturally leads Andy to ask Scott if he’s ever had a threesome. “I have,” he tells him, coolly sipping his drink. Young Eastwood has not, however, had the opportunity to lick Courtney Thorne-Smith. But Andy did send him home with a pair of Mazel boxer shorts, so at least there’s that.

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