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Why You Should Never Books in Order

Part ofErin Nicholas Books in Order

Browse the Why You Should Never books in order by Erin Nicholas, with trope-friendly summaries, series background, and tips on where to start.

Last updated: June 30, 2026

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Why You Should Never books in publication order

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10 books

1

Why You Should Never Kiss Your Boss

by Erin Nicholas

2009

Jessica's job is to keep Ben out of trouble during his suspension. The problem is, being around him is exactly what gets her into it.

2

Why You Should Never Kiss a Grump

by Erin Nicholas

2010

A grumpy hero, a woman who gets under his skin, and long-held attraction make this tropey rom-com title fit perfectly.

3

Why You Should Never Kiss Your Blind Date

by Erin Nicholas

2010

Danika's carefully arranged blind date goes wrong in a hurry, but the chemistry with Sam is impossible to write off.

4

Why You Should Never Kiss Your Ex-Husband

by Erin Nicholas

2012

A second chance starts with one kiss and quickly becomes a reminder that old feelings rarely stay buried.

5

Why You Should Never Kiss Your Fake Boyfriend

by Erin Nicholas

2012

A pretend date is supposed to solve one social problem, not create a very real romantic one.

6

Why You Should Never Kiss Your Enemy

by Erin Nicholas

2013

Old rivalry, sharp banter, and far too much chemistry make this one a very bad idea in all the best ways.

7

Why You Should Never Kiss Your Ex

by Erin Nicholas

2013

One date should have been easy to forget, but some relationships refuse to stay finished.

8

Why You Should Never Kiss Your Best Friend

by Erin Nicholas

2014

Trying to move on gets complicated when your supposed best friend suddenly looks like the right person all along.

9

Why You Should Never Kiss Your Roommate

by Erin Nicholas

2014

Living together is hard enough before unresolved attraction starts turning every shared space into a bad idea.

10

Why You Should Never Kiss Your Brother's Best Friend

by Erin Nicholas

2017

Family ties and long-standing rules make this romance messy from the start, which only makes the attraction harder to resist.

Why You Should Never books in chronological order

  1. Book cover for "Why You Should Never Kiss Your Boss"

    Why You Should Never Kiss Your Boss

    by Erin Nicholas

    2009Why You Should Never, Book 1
  2. Book cover for "Why You Should Never Kiss Your Blind Date"

    Why You Should Never Kiss Your Blind Date

    by Erin Nicholas

    2010Why You Should Never, Book 2
  3. Book cover for "Why You Should Never Kiss a Grump"

    Why You Should Never Kiss a Grump

    by Erin Nicholas

    2010Why You Should Never, Book 3
  4. Book cover for "Why You Should Never Kiss Your Fake Boyfriend"

    Why You Should Never Kiss Your Fake Boyfriend

    by Erin Nicholas

    2012Why You Should Never, Book 4
  5. Book cover for "Why You Should Never Kiss Your Ex-Husband"

    Why You Should Never Kiss Your Ex-Husband

    by Erin Nicholas

    2012Why You Should Never, Book 5
  6. Book cover for "Why You Should Never Kiss Your Ex"

    Why You Should Never Kiss Your Ex

    by Erin Nicholas

    2013Why You Should Never, Book 6
  7. Book cover for "Why You Should Never Kiss Your Enemy"

    Why You Should Never Kiss Your Enemy

    by Erin Nicholas

    2013Why You Should Never, Book 7
  8. Book cover for "Why You Should Never Kiss Your Best Friend"

    Why You Should Never Kiss Your Best Friend

    by Erin Nicholas

    2014Why You Should Never, Book 8
  9. Book cover for "Why You Should Never Kiss Your Roommate"

    Why You Should Never Kiss Your Roommate

    by Erin Nicholas

    2014Why You Should Never, Book 9
  10. Book cover for "Why You Should Never Kiss Your Brother's Best Friend"

    Why You Should Never Kiss Your Brother's Best Friend

    by Erin Nicholas

    2017Why You Should Never, Book 10

Series background & context

This series is Erin Nicholas leaning all the way into romance trope hooks. Every title tells you the bad idea up front, boss, blind date, fake boyfriend, ex, roommate, best friend, and then the book gets to prove why the bad idea is so tempting.

These are reissued stories from earlier connected series, so the bones are classic Nicholas. Strong attraction, lots of banter, family and friends hovering nearby, and a fast-moving contemporary-romance rhythm. The retitles make the entry point easier for trope readers who know exactly what flavor they want. If you are less interested in one big shared setting and more interested in picking a setup that sounds fun, Why You Should Never is probably the easiest Nicholas series to browse by mood. It is a very readable gateway into her backlist because the emotional beats are familiar and the packaging is simple.

Edited by

Richard Reis

Software engineer whose passion for tracking book recommendations from podcasts inspired the creation of MRB.

Anurag Ramdasan

Lead investor at 3one4 Capital whose startup expertise and love for books helped shaped MRB and its growth.

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