The New Adventures of Old Christine (2006)

S1E4 One Toe Over The Line Sweet Jesus

Richard discovers from a smug Matthew that Christine is on her fifth date with a guy named Burton. In a fit of jealousy, he decides to interfere, ruining their goodnight kiss and hurling lawyer jokes at Burton. However, when Richard attempts to mend fences by inviting Christine and Burton to dinner with his "new" girlfriend, his well-intentioned scheme quickly spirals out of control.