Night on the Town is a date night webisode, based on the "Special Edition" Night on the Town doll line.
Barbie, Chelsea and Madison are going on a triple date with River (Barbie's date), Hudson (Chelsea's date) and Sutton (Madison's date), and after a quick stop at an upscale clothing store, they buy some new outfits for their date to impress the guys. River, who was nearby and happened to see the girls (who didn't see him), calls Hudson and Sutton on their cellphones. After revealing what he saw to his friends, River (after looking over the outfit he was wearing at the time) points out that they have to find new outfits for their date with the girls. After doing some shopping, the guys manage to do so as well as getting flowers for the girls. Although the guys are late picking up the girls, they're quick to forgive them when they see how nice the guys look.
The morning after the date, the guys are hanging out at a coffeehouse talking about the date. All three of the boys had something really embarrassing happen to them during the course of their triple date with the girls:
- While River and Barbie were out on the dancefloor, River's pants ended up ripping, revealing his underwear.
- When Sutton smiled at Madison at one point, it turns out he had a bunch of food stuck in his teeth.
- Hudson got some drinks for himself and Chelsea, but while he was handing Chelsea's drink to her, he accidentally spilt it on her outfit.
River, Hudson and Sutton are worried that, after what happened on their date the previous night, the girls will never want to go out with them again. However, the girls eventually come in and assure the guys that, despite what happened, they ultimately had a nice time with the guys and want to continue dating them.