Are You There, Vodka? It's Me, Chelsea

In order to impress a fifth grade boy and to gain the respect of the girls at her school, Chelsea concocts a tall tale in which she is co-starring in a movie with Goldie Hawn. The lie quickly gets blown out of proportion, and things get even more complicated when Chelsea's father forces her to reveal the truth.

During her summer vacation on Martha's Vineyard, Chelsea pretends to be older than she is so that parents would allow her to babysit for money. After a few attempts, she gains renown as a babysitter, and the calls come pouring in. One of her calls, however is to look after a fourteen-year-old (even though Chelsea is really only twelve) and his "72-month-old" brother. She accepts, and chaos ensues.

Chelsea gets pulled over after drinking and driving, and is arrested and sent to the Sybil Brand Institute.

Chelsea returns home to find her father having urinary issues, conning people via his used car company and Chelsea's books.

Chelsea somehow finds herself falling for a red head, even though she doesn't exactly have an affinity for men of that hair color.

Chelsea is asked to go to London for the UK release of her book, and she decides to bring her recently single and unemployed friend along. Her friend makes reservations for the both of them at a restaurant where you dine completely in the dark, and when they arrive, they realize they've gotten more than they bargained for. After an unpleasant experience at the restaurant, they duck out to a nearby pub, where they meet what they assume to be a former rock star.

Chelsea and a friend retreat to a sketchy part of town in hopes of finding a massage place with openings. They come across a small shack operated by an Asian woman, and Chelsea assumes that it's a whorehouse. After a few minutes of a less than satisfactory massage, Chelsea complains, and trouble ensues.

Chelsea and her Persian boyfriend get stuck dog sitting for their friends. After they have sex on their friends' bed, her boyfriend lies naked watching TV and one of the friends' dogs comes up and begins licking his penis. Chelsea becomes very uneasy about it. They go to a party later and her Persian boyfriend holds that same dog in his arms the entire time. Later, they go to eat at his parents’ home and Chelsea can't get over the fact that his mother is rude and looks like a man. They break up and he is understandably upset calling her spoiled among other things. She later sees him with the same type of dog that licked his penis and a new girlfriend, and alludes to the penis licking incident and leaves happily.

Chelsea finds herself stuck going to the birthday party of someone she barely knows, and has no choice but to re-gift a used, but hardly played, board game. She also finds herself bartending at the dinner because the restaurant lacks one of her requirements: a full bar.

Chelsea decides she needs to lose weight before her birthday and signs up for a private kickboxing class. After losing enough weight to be proud, she decides to treat herself and pigs out on a mountain of junk food from Starbucks. After eating it all at her apartment, and taking out her energy with cleaning, Chelsea falls asleep and wakes up exhausted. Her friend calls and yells at her for not picking her up at the airport and Chelsea leaves to get her. On the way, she nearly drives into a group of fourteen-year-old girls, one of whom calls her a cunt. She gets out to yell at them for calling her this and they attack her.

Chelsea meets a little person who looks and acts a lot like her and they become instant friends. Soon she learns that her friend needs her help.

Chelsea gets dragged into going on vacation in Costa Rica with her father. The entire time she keeps emailing her brothers and sisters to get them to come and help her.