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Exclusive First Look: Walden Romances Hilary Duff (and Marilu Henner!) on 'Two and a Half Men'

Ashton Kutcher is caught in a generation gap in this sneak peek at the May 9 season finale.

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Being a handsome billionaire, Walden Schmidt has always had a way with the ladies. But even he's probably never experienced a love triangle like this.

The Season 10 finale of CBS's "Two and a Half Men" (airing May 9) offers a pair of new love interests for Ashton Kutcher's Walden: a ditzy young blonde, played by Hilary Duff... and her savvy grandmother, played by "Taxi's" Marilu Henner. And we've got an exclusive sneak peek at the trio's uncomfortable dinner together right here.

[Photos: Check Out All the Guest Stars Coming to TV for May Sweeps]

In the clip, Walden is trying his best to connect with his airhead date Stacey (Duff), asking her about the college degree she just earned in communications. Her response: "You know, it's like... talking and stuff." Her grandmother Linda (Henner) sighs: "A hundred and twenty grand."

Stacey then bluntly asks Walden if they're going to have sex tonight; if not, she'd rather ditch him to run off to a party with her friends. She leaves him to finish dinner with Linda -- not before running off to the little girls' room to throw up first, though. Yeah, after that display, we can't exactly blame Walden for dipping his toe in the cougar pool.   

[Related: 'Two and a Half Men' Is Returning Next Season... Without Angus T. Jones]

For the record: Duff is 25, and Henner is 61. (And Demi Moore is 50. Just sayin'.)

The Season 10 finale of "Two and a Half Men" airs Thursday, 5/9 at 8:30 PM on CBS.

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