Sept. 29, 2025

Is Dating Your Coworker Ever Worth It?

Is Dating Your Coworker Ever Worth It?

In this episode, Kaila and Kyle debate whether you should or should NOT pursue your office crush. That’s right—we’re talking office romance this week, and Kaila and Kyle hold strongly opposing positions on the matter, based in part on their own personal experiences.

00:00 Intro

02:57 Historical context for the conversation

04:23 Kaila’s opinion on pursuing a relationship in the workplace

08:19 The types of jobs where office romance becomes more likely

15:53 The most important thing to remember when considering a romantic relationship with a coworker

18:58 Power dynamics in coworker relationships

21:02 Disclosure

22:35 Never be the main character

26:28 Perception

28:19 Kaila’s 4 conditions for pursuing an office romance

This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.

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Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!

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