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Claude scores a date with Charlie from travel after accidentally throwing her hair on his face. They have a wonderful time together, and the next morning Claude is ecstatic about it. Will introduces her his godson Oliver, and asks Claude to show him around town. He asks her out on a date, and ends up accepting to go out with him after Will pressures her to. Claude tries to jiggle dating two men, but her scheme soon falls apart when Will comments on her date with Oliver in front of Charlie, who leaves heartbroken. Claude feels bad gets advice from Ramona and Lydia on how to dump Oliver and get back with Charlie. Meanwhile, Kipp starts sucking up to Mr. Turnbach's son hoping for a chance of a promotion.
Episodes
1Pilot 2Ice Cream With Lydia 3Claude the Liar 4Queen of England 5The Vacation 6The Pole 7Future Shock 8Meet the Folks 9Claude the Heartbreaker 10One Office Party Too Many 11A Claude Casey Production 12Claude's Got a Secret 13Telephone 14High Maintenance 15Valentine's Day 16Breaking Up 17Picture Perfect Party 18The New Guy 19Oh Papa 20A Little Love for Lydia 21Save the Squirrel, But Bet the Over/Under 22The Umbrella (1)