Contemporary, Fiction, New Adult

Jessica Darling quintet by Megan McCafferty

Jessica Darling helped me survive high school. I was first introduced to the delightfully snarky, sarcastic and spunky teen heroine of Sloppy Firsts when I was a freshman in speech and debate practice after school one autumn afternoon back in 2003. A frenemy of mine was testing out an excerpt from Second Helpings for a speech competition and it was certainly effective: I remember nothing else of the speech and debate season but hearing about Jessica handle the popular girls in a Jersey mini-mall still resonates in my head a decade plus later.

The series consists of five books and originally Megan McCafferty only intended to write the first two and they stand alone very well. I also read Second Helpings before Sloppy Firsts and while slightly confusing, I think it just made me love Marcus even more. I also had the great pleasure of meeting Megan McCafferty my junior year at Pitt and she has now started a Jessica Darling in middle school series which is quite wonderful as well, even though it differs from the originally established timeline.

Sloppy Firsts Synopsis

When her best friend, Hope Weaver, moves away from Pineville, New Jersey, hyperobservant sixteen-year-old Jessica Darling is devastated. A fish out of water at school and a stranger at home, Jessica feels more lost than ever now that the only person with whom she could really communicate has gone. How is she supposed to deal with the boy- and shopping-crazy girls at school, her dad’s obsession with her track meets, her mother salivating over big sister Bethany’s lavish wedding, and her nonexistent love life?

Sloppy Firsts looks at Jessica’s predicament as she embarks on another year of teenage torment – from the dark days of Hope’s departure through her months as a type-A personality turned insomniac to her completely mixed-up feelings about Marcus Flutie, the intelligent and mysterious “dreg” who works his way into her heart.

Series Review

There are, thus far, 8 books about Jessica Darling. Therefore, understandably, my review cannot simply be contained to one book, each reading changes and effects how I view the books so it may be a bit garbled and I’ll try to review book by book without any spoilers, but bear with me!

Sloppy Firsts I have read only once and I did so after reading Second Helpings, the stronger of the pair, writing wise. I was introduced to Jessica after Marcus, after her sister’s wedding, and after she’s met, and discovered the truth about, Hyacinth Anastasia Wallace. All of these things take place in Sloppy Firsts but I didn’t know the full story. At the start of Sloppy Firsts, Jessica is broken, though she does her best to hide it. Her best friend Hope has moved away and while Hope does not actually physically enter the story until the end of Second Helpings, I had already met her. But her influence on Jessica’s life is profound – she is her best friend, her confidant. For a young girl to have such a strong friendship is an incredible thing to behold and when that friendship is no longer as present, depression can quickly ensue. Throughout Sloppy Firsts, Jessica must handle changing feelings, embarking on a friendship she fears Hope would disapprove of, and betrayal of her trust by a new friend. The waters of high school are choppy and Jessica must learn how to cross them safely without her navigator and first mate, Hope.

Second Helpings: My copy of Second Helpings is thoroughly beat up. I love the book, I’ve read it over and over and over again whenever I have been in need of inspiration for my own writing, or when I just want to read about characters that I love dearly. So who came up with it first, JK Rowling or Megan McCafferty? Both have a character known as “he who shall not be named” and Jessica is horribly mad at the one who walks around her high school’s halls. Her feelings have been hurt, irrevocably, she claims, and she swears to never forgive the sinner. Second Helpings is set during Jessica’s senior year and from the very start, it seems as if all hell will be breaking loose. She must deal with national tragedy (9/11), personal tragedy when a beloved family member is lost, and coming to grips with her own moral quandaries and whether or not a friendship is still a friendship if secrets are kept.

Charmed ThirdsFourth Comings: In which Jessica follows her heart and goes to her dream college and lands what she believes to be her dream job. Charmed Thirds & Fourth Comings are my two least favorite books and for the longest time I would not read them. Laura had started them and was unimpressed. However, when I met Megan McCafferty, I needed a book for her to sign and so I picked up a copy of the new edition of Charmed Thirds. I will cherish it always as it bears McCafferty’s lovely looping signature and I got to meet her with some of my best college friends. However, Jessica, is just not Jessica in these two books. While Sloppy Firsts & Second Helpings cover roughly a year and a half between them, Charmed Thirds & Fourth Comings span almost 8 years and everything feels so rushed.

Perfect Fifths: When I went to hear Megan McCafferty speak, she read aloud from the recently released Perfect Fifths and I was hooked. It was the first time we the readers get Marcus’ point of view and WOOHOO!!! I powered through Charmed Thirds & Fourth Comings just to get to the part Megan McCafferty read in the dimly lit auditorium of Frick on my beloved Pitt’s campus. As the Sisterhood of the Traveling Pants series did years later, the fifth book takes place when the main characters are in their late twenties. And it is pure literary gold. It’s an ending, without being final but also without fully answering all the questions that have so far gone un-answered. But it is perfect, perfect for you, yes, you to enjoy.

Jessica Darling is a relatable girl for those who grew up feeling pressure in high school, fearing being misunderstood, missing their best friend, wondering when their lives would really begin and if their relationships with others were/are meaningful. Jessica, Marcus, Hope, Bridget, Percy, Bethany and even Mr. and Mrs. Darling make up an unforgettable cast of characters. As is the case with all series, there high points and low points, both within the story and the story telling but all-in-all, Jessica is a character to depend on and a role model for those who don’t quite fit in, feel a little lost or who simply want a shoulder to cry on. She’s your girl.

Series Rating: 7 out of 10 stars

Sloppy Firsts Edition: Paperback • $13.99 • 9780609807903 • 304 pages • published August 2001 by Broadway Books • average Goodreads rating 3.94 out of 5 • series finished April 2010

Megan McCafferty’s Website

Sloppy Firsts on Goodreads

Get a Copy of Sloppy Firsts

Jessica Darling

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