"Anna dislikes being stuck three-quarters of the way down a chimney. She really does. Not to mention, she's still going round North America, and there's, like, three continents still to get through in about as many hours."

Hudson Ellis is good at his job. Somehow, he manages not to annoy people when he knocks at their doors and asks them to contribute to the charity he works for - instead, he gets them to sign up for sponsoring programmes and fish whatever spare change they have out of their pockets. Even the infamously tough residents of New York City are falling victim to Hudson's easy-going ways and wide smile; that is, until one woman renders him speechless with sarcastic refusals and slams her door in his face. Perhaps Hudson would be able to forget her - if it wasn't for the fact that she lives on the same floor of the next apartment over, and they both have floor-to-ceiling windows that allow for a rather generous view into each other's flats.

Kennedy (Kenna) isn't known for her beauty. She's never been complimented on her appearance unless being called beautiful by your family counts, and to Kenna- it doesn't. Sick of being ignored because of her looks, Kennedy gives herself a makeover but it isn't very successful. After encountering a crying Marissa Rivers on the behalf of her obnoxious brother, Noah, she becomes acquaintances with the girl. After a chat about Kenna's failed efforts at makeup and how she's a nondrinker, she offers Kenna the help of her and her friends. Kenna graciously agrees but there's a catch. Kenna will have to be the girls' designated driver to the next few parties that they want to attend until she can do her own makeup which may take a while but what happens when Kenna accidentally gets drunk at one of the parties and Noah has to bring her and the other girls back to their home? She gets involved in a lot more than she planned. And it seems as if all she wanted was to become beautiful.