Grant drops some knowledge on Craig to help him with the ladies as Kenny approaches the beautiful blonde who's eyeing him. Without Grant to guide him, Kenny opens with, "Try to keep it quiet, but I've got a half a pack of Razzles in my pocket. It's the candy that becomes gum" -- which miraculously works. Sometimes you get lucky. Will took off his wedding ring while wingmanning for Kenny to make it more convincing…and then they bump into a woman from Theresa's book club. Will runs home to spill the beans to Theresa, but Theresa just laughs it off. Will's relieved, but insulted that she thinks he can't meet women.
The next day, Kenny explains that nothing happened with his date. But that's not as shocking as his reason: Brenda is the only girl he's ever slept with, and he's worried he's not any good at it. All the elaborate stories he told back in the day: all fake. "I'm afraid to even ask about the woman from Alabama with the banjo," Craig says. "Oh…Susanna?" Kenny replies. Yeah. So Kenny sucks it up and goes to the source, and asks Brenda. Her response? "There were a lot of things in our marriage you were terrible at, so many areas where you sucked and were deficient and disappointing. But things in the bedroom were always great." He'll take it.
Will peacocks up like a Jersey Shore twentysomething and tells Theresa he's going out with the boys; still no reaction. "I'm wearing this cool metal shirt, I tell her the saleswoman flirted with me, and all she says is I should pick up the dog poop on my way out." Craig and Grant double date with the ladies from the club. But it turns out Craig's woman is just wingmanning for her friend who's got a crush on Grant. But Grant's with Brenda…so the evening ends in disappointment for everyone. Mostly Craig though, who shelled out for a Hummer limo and a lot of expensive champagne.
At the book club, Theresa sees a picture of the girl Will was talking to. She's gorgeous. Theresa finally snaps. When Will gets home, he and Theresa have it out, and Will makes it clear he just wants Theresa to think he's sexy. She does -- she doesn't worry about him having an affair because he's a great guy, not because he couldn't have one if he wanted. Meanwhile, Kenny heads back over to Sheri's house to see about a second chance. She's wants to hang out, but it turns out she lives with her hard-of-hearing and somewhat senile grandma and tonight is Dancing with the Stars night. Kenny sticks it out, and it pays off: He ends up sleeping with her while Grams watches TV. In the same room. Yay?