I'll Pay $5,000 for a Swimsuit That Fits Me!!

by Imelda Whelehan

Fielding captures that same neurotic, self-aware humor about modern dating and body image that made Cathy so relatable, but through a 1990s British lens with diary entries that feel like you're reading a friend's honest confessions. Both protagonists are hilarious precisely because they're brutally candid about their insecurities rather than pretending to have it all figured out.

by Yu.V. Egorov

This 2013 collection of illustrated essays has Cathy's DNA—the exaggerated internal monologues, the way anxiety spirals into absurdity, the unflinching look at how we sabotage ourselves—but Brosh's crude drawings and deadpan delivery give it a completely different energy. It's what Cathy might look like if she were created by someone raised on internet culture instead of newspaper comics.

by Author

Here's the surprise: this 2008 novel has almost nothing to do with swimsuits or dating, but it shares Cathy's gift for finding warmth and humor in ordinary people's messy lives. The epistolary structure means you're reading letters and diary entries from characters who are funny not because they're trying to be, but because they're genuinely themselves—that same authenticity that made Cathy's strip work.

by Chelsea Handler

Handler's 2007 memoir essays have Cathy's confessional tone—the willingness to be the punchline of her own story—but with a wilder, more reckless energy. She's tackling the same territory of modern female anxiety and romantic mishaps, just with more tequila and fewer office politics, which gives you that comedic voice you loved without the exact same setting.

by Graeme C. Simsion

Simsion writes about dating and self-discovery with the same gentle, funny touch Guisewite brought to Cathy, but from a male perspective and with a protagonist who's genuinely struggling to understand social norms rather than just anxious about them. The humor comes from the gap between how the character sees himself and how others see him—that same comedic engine that powered the strip.