Stumbling Into Love Books in Order

Part ofRiley Hart Books in Order

See the Stumbling Into Love books by Riley Hart in order, with quick summaries, series background, reading order notes, and help deciding where to start.

Last updated: July 5, 2026

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Stumbling Into Love books in publication order

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3 books

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Awkward Love

by Riley Hart

2020

Awkward grad student Jameson bids on a date hoping for a summer fling and gets much more than he bargained for. Secret complications only make Will harder to resist.

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Stupid Love

by Riley Hart

2020

Snarky neighbors Elijah and Shaw trade jabs, bad advice, and escalating attraction. What begins as annoyance becomes a funny, messy fall into real feelings.

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Messy Love

by Riley Hart

2021

Danny offers recently out Jonathan a room and maybe a little fun. Instead, both men tumble into something tender, sexy, and harder than expected to keep casual.

Stumbling Into Love books in chronological order

Stupid Love
by Riley Hart
2020Stumbling Into Love, Book 1
Awkward Love
by Riley Hart
2020Stumbling Into Love, Book 2
Messy Love
by Riley Hart
2021Stumbling Into Love, Book 3

Series background & context

Stumbling Into Love is Riley Hart's rom-com side with the volume turned up. The books are modern, chatty, and full of men who insist they know what they are doing right before they make an emotional mess of everything.

Stupid Love, Awkward Love, and Messy Love all play with that gap between confidence and reality. There are annoying neighbors, auction dates, secret hookups, friends and siblings tangling the emotional web, and plenty of banter that only barely hides real vulnerability. Even when the books get into heavier backstory, the tone stays quick and inviting.

If you like contemporary romance that feels fun without being shallow, this series is a good lane. The titles tell you a lot, really. These are people stumbling, fumbling, getting flustered, and somehow finding exactly the right person in the middle of the chaos.