The 8 Most Lovably Awkward Characters in YA Books

Awkwardness is one of the best traits in a literary character. On one hand, it can provide laugh-out-loud humor, a chance for you to chuckle at someone else’s (fictional) misfortune. And on the other, it can offer a calming sense of reassurance — that feeling of “Ahhh, good, someone else has gone through that, too.” As you’ll be able to tell by the title of our new novel — A Totally Awkward Love Story — we packed our book full of face-reddening, ultra-cringe-worthy teens and moments, so we thought we’d pay tribute to a few of the greats that came before!

1. Harriet Manners (Geek Girl series)

Holly Smale’s brilliant series about a teenage geek-turned-fashion model features one of the best and most awkward protagonists out there. Whether Harriet is accidentally destroying expensive items of clothing, incurring the wrath of her best friend and parents, or being discovered hiding under a table by the hot boy she likes, she’s one of the funniest and likable characters in YA lit.

2. Adrian Mole (Adrian Mole series)

Full disclosure: We are from the U.K., and we have absolutely no idea whether Adrian Mole is a big deal in the U.S. But if you haven’t heard of him, check him out! The Secret Diary of Adrian Mole Aged 13 3/4 kicks off Sue Townsend’s fantastic series, which catalogues Adrian’s highs and lows (mainly lows) as he tries to muddle his way through adolescence. He writes terrible poetry, fails miserably with girls, and — in one chapter — tries to sniff glue and ends up in the hospital with a model airplane stuck to his nose. He is basically a glorious, bumbling model of male teenage awkwardness.

3. Ron Weasley (Harry Potter series)

Obviously Neville, Luna, and even Harry himself could all have been strong contenders for the title of Most Awkward Potter Character, but we’re going to give the award to good old Ronald Weasley. Why? Well, where do you start? Perhaps the old dress robes he had to wear to the Yule Ball? Vomiting slugs? Dancing with Professor McGonagall in front of the whole class? Going insanely dewy-eyed when he drinks the love potion? And many, many more moments…

4. Georgia Nicolson (Confessions of Georgia Nicolson series)

These books by the late, great Louise Rennison are everything good YA should be — funny, relatable, honest, and EXTREMELY awkward. Angus, Thongs and Full-Frontal Snogging was one of the main inspirations for our novel, as we wanted to try to write a Louise Rennison-style book full of cringe-worthy comedy, but for slightly older teen readers. Georgia Nicolson is such a great character, and whether she’s turning up to a party dressed as a stuffed olive or shaving one of her eyebrows off, you can’t help but love her.

5. Cassandra Mortmain (I Capture the Castle)

Cassandra lives through her books and her journal and mostly has her head in the clouds. She is the ultimate daydreamer and doesn’t always pay attention to what happens around her. She seems to always think the wrong thing or say the wrong thing or do the wrong thing … often with highly embarrassing consequences. She has none of her older sister Rose’s beauty, grace, or poise, but you’ll still want to be her because she is a true eccentric.

6. Nigel Molesworth (Molesworth)

Another slightly obscure British choice here, so we’re sorry — but, again, if you’ve never heard of Nigel Molesworth, he is well worth seeking out. He’s essentially a scruffy, over-imaginative, awkward, and usually quite grumpy schoolboy, who talks the reader through all aspects of his life, from how to avoid the craziest teachers to how to attract girls (he’s not very successful at either). But Nigel isn’t just super awkward; he’s also surprisingly deep. See lines such as: “History started badly and hav been gettin steadily worse” and “Grown ups are what’s left when skool is finished.”

7. Matt Gratton (Swim the Fly series)

Don Calame’s books are a great example of excellent teen YA aimed at boys. In Swim the Fly, Matt and his friends set themselves the goal of trying to see a real, live girl naked before the end of the summer and, as a result, Matt ends up humiliating himself in some of the most amusing and embarrassing ways possible.

8. Simon Spier (Simon vs. the Homo Sapiens Agenda)

The protagonist of this brilliant book by Becky Albertalli is awkward in a less cringe-inducing — and perhaps more relatable — way than most of the others on this list. He is basically just a 16-year-old boy trying to figure out who he is and feel comfortable in his own skin, which is not helped by the fact that he’s being blackmailed about a GIGANTIC secret (no spoilers here, you’ll have to read it). Simon tries to deal with the madness of love, friends, family, and school, all while grappling with this huge secret, which makes his life extremely awkward … and highly entertaining.

Who are your top lovably awkward characters in young adult books? Let us know in the comments section below!