Upright Citizens Brigade and Second City alum Monika Smith is heading to CBS’ Two and Half Men.

The former prankster on MTV’s Disaster Date is scheduled to guest star on the Oct. 24 episode as Kiki, a girl Walden (Ashton Kutcher) and Alan (Jon Cryer) meet at a bar.

On the Charlie Sheen-less Men, Alan is turning into the ladies’ man as his roommate-to-be Walden mends a broken heart.

The casting follows news that True Blood’s Joe Manganiello is heading to the CBS comedy as the new boyfriend to Walden’s ex-wife Bridget (Judy Greer).

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