Don Juan De Van Nuys (S01E09)

Feeling down about her lack of romantic prospects, Jennifer longs for some attention. After Jack clears out the rest of his belongings from her basement, she decides to spruce up her home. She hires Matt, a 20-year-old recent arrival from Jack's building, who was a star athlete in high school. When Jack warns Jennifer that Matt tends to date the women he works for, she becomes determined to pursue him. Meanwhile, Tiffany is captivated by Matt, but Jennifer insists she steer clear to eliminate competition. However, when Matt shows little interest in her and instead connects with Mrs. Wilson, who has a fuller figure, Jennifer vents to Jack about her insecurities.