The New Adventures of Old Christine (2006)

S4E4 Snakes On A Date

Christine is juggling a demanding job while striving to be a supportive mom. When Ritchie expresses his desire to join the school's reptile club, he reminds her that all she needs to do is submit the permission slip on time. However, when Christine realizes she’s neglected this once more, she turns to the Reptile Guy (Jeffrey Tambor) for help. He agrees to consider her request, but only if she goes on a date with him. Despite his unsettling demeanor, Christine is resolute in her decision to not disappoint Ritchie, so she reluctantly agrees.