About A Boy, Writing About Girls
Let's talk a little about Simon Rich's fifth book. His latest is a collection of short stories, about both love and anti-love.

Simon Rich, at 29 years old, is at an age now where he’s a successful writer. He had quite a moment being a super young this and youngest ever that, and he’s definitely accomplished more in his post-collegiate years than what most aspiring writers will accomplish in their entire lifetimes. But it’s also apparent that Rich works hard and operates like some kind of wordsmith factory. Sometimes even I can’t catch up with everything he writes, and I usually read (or watch) everything Rich has penned.

Last Girlfriend is the kind of book that I felt appeared at stores one day and I had absolutely no idea it was even in the works, considering Rich’s second novel What In God’s Name?—which, by the way, is an excellent romp if you’re into romantic comedies—was only released five months prior to Last Girlfriend. Simon Rich sure knows how to stay busy, focused.

Last Girlfriend is an obvious choice for any Simon Rich fan and the more I think about it, it’s also a good intro to his writing in general, especially for anyone who is weary of “humor books.” And that’s because, unlike a lot of other humor stories I’ve read, I always felt like Rich’s pieces were were never trying too hard. He’s got an easy-going way with words that convey smart and funny ideas but that are written simple enough for even a child to read, even if young kids won’t get the joke. (Which makes total sense why he is also a writer for Pixar.) Another place to get more familiarized with Simon Rich are his pieces from previous “Shouts and Murmurs.” Lots of great archived gems in that online treasure trove.

Back to the book. There are plenty of hearty laugh-out-loud moments but Rich also knows how to leave the reader in a dark place, at least for me, as a girl. A handful of Rich’s pieces have a Walter Mitty/James Thurber-esque spirit to them: they’re goofy, poignant, sad, uplifting, funny, and also not funny, like when (non)-“love interests” appear to be so villainous. I know, confusing emotions abound! But then I saw Rich dedicated this book to his own girlfriend Kathleen so I felt less weird after that. At the end of it all, every story does come from a really sincere place (and from the peculiar inner-workings of what is Simon Rich’s mind).