Guess Hoe's Coming to Dinner is the third episode of The Boondocks. It premiered on November 20, 2005.
Riley, Huey, and Granddad are shopping at the grocery store where Granddad is looking at various sexual enhancers, when the calm is broken by an angry child craving candy from his mother. Granddad offers his help by lending the mother his belt and showing her the whipping motion. A 20-year-old blonde dressed in skanky clothes admires his chivalry and introduces herself as "Cristal (like the champagne)". When checking out her wares she shows Granddad her special edible french whipped cream. She also buys honey, chocolate sauce, a big bread, sausage and all sorts of condoms. She then pays $153.12 with small bills that she keeps in a bundle. Outside the store, Cristal asks Granddad if he's interested in going out on a date and he tells her he's got coupons for the "Red Lobster". On the way home, in the car, Riley asks Granddad if he really realizes that: "That light-skinned hoe was a hoe?". This follows with Granddad slapping Riley hard without watching the road.
At home, Huey also questions why a 20-year-old would want to go out with a man Granddad's age. But Granddad insists that he laid his game down "quite flat". At the "Red Lobster" Cristal is gulping down the cheddar biscuits like a man. The waiter comes up and asks: "Doggybag?" to which Cristal answers:
"A 'doggy bag' is 90 bucks, a tea bag is 50, but I have to actually excuse me right now, 'cause I'm actually on a... 'real' date". At home Huey and Riley are contemplating what a 'hoe' really is. Walking home from the dinner Cristal tells Granddad she looking for a man that could "swoop in and save me, from, you know... work". Then we see several scenes with Cristal dragging granddad around making him buy her stuff. Later Cristal is whooping Riley's butt in PlayStation and uses foul language, and drinks the last of the orange juice directly from the carton and puts it back in the fridge (Granddad's pet peeve). Huey Riley Flo and Katie confronts Granddad about Cristal and tells him she has to go, but he refuses to accept that she's a hoe. So Huey asks him if she "ducks under the table every time a dude in a purple suit walks in?" which he admits she does "but a lot of people do that". Riley asks him if she can "run really, really, really, really fast in high heels?" which he, after a brief recollection, says that she does with "little above average" speed. Huey asks him if she keeps asking him if he's a cop. No! Is the fast answer, moments after Cristal walks up and says: "You know you have to tell me if you're a cop or it's entrapment". But Granddad still refuses to accept the truth. Huey then confronts Cristal directly and tells her that she has to go because she's a lazy hoe. But she doesn't want to, she wants to live the life too, so Huey has a plan so he tells the others
The next day Huey and Riley hide in the car and follows her during the day taking pictures of her: Paying her pimp, outside the "House of Cheeks", a strip club and running from the police. They show the pictures to Granddad who asks her about them and she says: "That's not me. I can't believe you would digitally alter pictures of me". And she manages to put the blame on the children. Then the doorbell rings, Riley opens the door and yells: "It's a niggah in a purple suit". This is Cristal's pimp called "A Pimp Named Slickback" (not just Slickback, the whole thing). Granddad asks Cristal who he is, and she confirms: "He's my pimp". And finally Granddad has to realize that she's a hoe (Cristal, Riley, and Huey says it together,"Yes, I'm/she's a hoe", split screen) .
Cristal has to go with him and she says her goodbyes. A Pimp Named Slickback drives away without her and she runs after the car. Granddad is still assured that she will be back and stays up all night waiting for her, and the episode ends with Cristal running after A Pimp Named Slickback's car and Huey's voiceover saying:
"One thing I learned though...she sure can run in those heels."
- One of the men who was checking out Cristal bears a resemblance to Jin from Samurai Champloo.
- This is the first episode in the series that Uncle Ruckus does not make an appearance.