Sloppy Firsts (2001), Second Helpings (2003), and Charmed Thirds (2006) by Megan McCafferty
It begins in January 2000 (remember Y2K? The references are so quaint!) when Jessica Darling is a sophomore in high school, and goes through January of 2001. When the book begins, her best friend Hope has just moved away. Her older brother Heath died of a drug overdose and her parents thought it would be better for them all to leave New Jersey and move to Tennessee. Jessica is bereft without Hope. Early in the book, she has a strange encounter with Marcus Flutie, a druggie friend of Heath's who Jessica wants to avoid. But somehow he convinces her to pee in a yogurt cup for him so he'll pass a drug test, a crime which she heretofore refers to as the Dannon Incident. It is also the beginning of her long, complicated relationship with Marcus.
Second Helpings begins the summer before her senior year and goes through graduation, and I'm already feeling like it was a terrible idea to combine all three of these books into one post so I'm going to leave out a lot of details. Her relationship with Marcus is still a very slow burn and she ends up dating someone else for a while before she and Marcus find their way to each other. But it's all further complicated in Charmed Thirds when she is in New York attending Columbia and Marcus is in California attending some experimental Buddhist college.
There was a lot to like though! The first book was definitely an angst-filled, neurotic, kind of silly look at high school. Jessica refers to her friends as the Clueless Crew because she doesn't really like them and finds them shallow and vain and slutty, but still hangs out with them because that's just who is left after Hope moved away. She doesn't have a great relationship with her parents; she's pretty sure her mom wishes she was more like her older sister Bethany, and her dad doesn't know how to talk to her about anything except running, which she eventually stops because of an injury, to his great disappointment.
In the second book, she is part of a pre-college summer program where she takes a writing class with a bunch of other students who take themselves way too seriously, and an instructor who ends up having a big influence on her and her future. Also near the beginning of this book 9/11 happens, which greatly adds to her angst especially since she has decided to apply to Columbia in New York. Her parents have never wanted her to live in New York, and they definitely don't now. Jessica gets some great advice from her grandmother Gladdie, who is in a nursing home where Marcus works. She talks to Jessica about World War II to help her put 9/11 in perspective, and tells her she needs to do what she loves without being afraid of what could happen. Gladdie also loves Marcus, and I loved everything about this whole storyline involving Gladdie.
There is so much more that happened in these books that I didn't even touch on. I was surprised that I remembered it as a fun, light teen romance and that is really not at all what it is. First of all, her relationship with Marcus Flutie is very intense but in a hate-turned-love-turned-dislike-turned-various-other-things kind of way. It was really up and down and not totally resolved by the end of the third book. Second, there's a lot more to this than her relationship with Marcus - her friendships are a big part of this, and her family (particularly her rocky relationship with her sister), and everything relating to just growing up and trying to figure out who she is and what she's going to do. I'm very glad I finally went back and read these books again; they were just what I needed to read at the time.
When I first went into Goodreads to add Sloppy Firsts to my Currently Reading shelf, I was surprised to see that there are actually 5 books in this series because when I read the series there were only 3 and I guess I thought it was a trilogy. I wasn't planning to read the last two, but during the third book I impulsively requested the fourth in case I wanted to keep going. I still haven't decided yet, though I've got a stack of other books out from the library so even if I do decide to continue the series, it might not be for a bit.