Precocious schoolgirl Jamie Kelly (Emily Alyn Lind) keeps a diary where she documents her daily struggles at Mackeral Middle School which include competing with her nemesis, pretty and perfect Angeline (Sterling Griffith) for the boy of her dreams, Hudson Rivers (David Mazouz). When Jamie is not hanging with her ill-tempered troublemaker best friend Isabella (Mary-Charles Jones), dodging her mom's experimental cooking or indulging flights of fancy while bursting into song, she loves to paint and draw. So she is horrified when Assistant Principal Devon (James Waterston) says the art department might be first to go now the school faces severe cut-backs. Their only hope rests with a student winning the state's annual jump-rope competition or Jump-A-Thon. Naturally, perky Angeline volunteers to compete, so Jamie signs up too. With Isabella's help, Jamie sets out to show up her nemesis by collecting even more sponsors but ends up in a heap of trouble.
Written in the first person, Jim Benton's best-selling series of children's books have been compared with Sue Townsend's Secret Diary of Adrian Mole though one imagines the filmmakers behind Dear Dumb Diary had the hugely successful Diary of a Wimpy Kid movies in mind. In the wake of that boy-centric kid lit franchise producers have tried to tap into the tween girl end of the market with thus far only middling success. Both Ramona and Beezus (2010) and Judy Moody and the Not Bummer Summer (2011) were likeable films but neither packed theatres quite like Wimpy Kid. Produced by kid lit champions Walden Media, Dear Dumb Diary was made for television and thus presumably considered a comparatively low-risk grab at a tricky demographic. It is girlier than a stack of glittery pink cupcakes. Kristin Kanggi styles the entire film to mimic the hyper-manic day-glo sensibility of the pre-teen heroine. She matches star Emily Alyn Lind's near-exhaustingly perky performance with a relentlessly sparkly mise-en-scene with zany animated flights of fancy and big splashy musical numbers.
Kanggi has a background in musical theatre. Having staged live shows for the Pussycat Dolls she went on to develop the original theatrical version of Rock of Ages but conceded directing duties to Adam Shankman for the disastrous movie adaptation. As a result of her skill the musical numbers are dynamic and visually engaging. It helps that the songs, though unlikely to impress those with mature musical tastes, are disarmingly witty and blessed with a catchy pop beat likely to beguile the under twelve set. Among the most memorable musical sequences are the jump-rope fantasia of "My Awesomeness is Awesome" wherein Jamie imagines herself dressed like Uma Thurman in Kill Bill (2003) battling ninjas and the dour lunchlady's hilarious cabaret ode to the joys of meatloaf! Much of the film is winningly weird while on a psychological level certain aspects ring true, such as a child's tendency to misinterpret adult relationships or the way Jamie projects her own insecurities onto Angeline. She is so convinced the pretty blonde popular girl is out to get her she fails to realize her relationship with the comically, if alarmingly mean-spirited Isabella is more poisonous.
Coming of age stories often conclude when the child hero or heroine realizes the world is more complex than they thought it to be. Dear Dumb Diary negotiates that path but stumbles at the end where it abruptly takes back everything Jamie has learned for the sake of a cheap gag and muddles its own moral message. The film tries to have things both ways, on the one hand satirizing the upbeat philosophy of High School Musical (2005) (at several points a chirpy cheerleader echoes the HSM catchphrase "We're all in this together!" but ends up booed by her more cynical schoolmates) yet half-heartedly trots out the same platitudes. At least the musical comedy set-pieces are funny and the performances good. Brassy little Lind would make a great Annie (1982). The end credits have cast and crew sing along with Jamie's pop-rocker "Thanks for Listening", suggesting this was a fun experience for all. Some of that fun reverberates with the viewer.