Two and a Half Men (2003)

S2E19 A Low, Guttural Tongue-Flapping Noise

After Charlie brings Alan to an optometrist, they find themselves at a café where they unexpectedly run into Charlie's ex, Sherri. During their time there, Alan becomes intrigued by Sherri and resolves to ask her out. However, he struggles with the fact that she was once involved with Charlie, making the situation complicated for him.