What Are The Longest-Running Funny Romance Books Series?

I've been obsessed with funny romance series for years, and one that stands out for its longevity and humor is Janet Evanovich's 'Stephanie Plum' series. Starting with 'One for the Money,' this series has been making readers laugh since 1994. Stephanie, a bounty hunter with zero skills but endless luck, gets into the most absurd situations, and her love triangle with Morelli and Ranger keeps things spicy. The books never take themselves too seriously, and the humor is both slapstick and witty. With over 28 books and counting, it's a marathon of laughs and lighthearted romance that never gets old.

When it comes to long-running romantic comedy series, few can match the charm and staying power of 'The Bridgerton' series by Julia Quinn. While it's known for its Netflix adaptation, the books have been delivering Regency-era romance with a modern, humorous twist since 2000. Each book focuses on a different Bridgerton sibling, blending witty banter, societal satire, and heartfelt love stories. Daphne and Simon's dynamic in 'The Duke and I' sets the tone, but later entries like 'Romancing Mister Bridgerton' and 'To Sir Phillip, With Love' keep the laughs and swoons coming.

Another hilarious gem is the 'Psy-Changeling' series by Nalini Singh, which mixes paranormal romance with sharp humor. While it’s more fantasy-driven, the interactions between Psy and Changeling characters are downright comedic at times, especially in books like 'Slave to Sensation' and 'Play of Passion.' The series has been running since 2006 and shows no signs of stopping, proving that even supernatural love can be laugh-out-loud funny.

For contemporary fans, Jennifer Crusie's 'Bet Me' and its loosely connected stories offer a masterclass in romantic comedy. Though not a strict series, her books share a universe of quirky characters and absurdly funny situations. The dialogue is snappy, the romance is warm, and the humor feels effortless—qualities that make her work timeless.

If you want a mix of humor and romance that spans decades, look no further than P.G. Wodehouse's 'Jeeves and Wooster' stories. While not strictly a romance series, the antics of Bertie Wooster and his long-suffering valet Jeeves are packed with romantic subplots and hilarious misunderstandings. The series began in 1915 and still delights readers with its wit and absurdity. Bertie's endless engagements and Jeeves' clever fixes are a recipe for laughter.

For something more modern, the 'Holiday' series by Jenny Colgan is a delightful pick. Starting with 'The Little Shop of Happy Ever After,' these books blend small-town charm, bookish humor, and sweet romance. Each standalone story in the series has its own quirky couples and laugh-out-loud moments, making it perfect for readers who want consistency without commitment. Colgan’s writing is cozy and funny, like a warm hug with a side of giggles.