
Aug 8, 2026
7 min
Should You Sleep With Your Boss?
Sleeping with your boss can feel exciting, validating, and intensely attractive—but it can also create a complicated mix of secrecy, power, guilt, career risk, and emotional confusion.
In this episode of The Self Help Briefing, Mike and Jen unpack why workplace affairs can feel so intense, how power imbalances can affect the relationship, and why that uneasy feeling in your gut may be worth paying attention to. They also discuss the possible professional and emotional consequences, the questions to ask yourself, and what it means to make a decision that lines up with your values and long-term goals.
Read the Original Article
Podcast inspiration came from the article: I’m Sleeping With My Boss But Feel Weird where apparently a male employee who works in the mailroom has been sleeping with his female boss.
Read the article at Couples Counseling Chicago
Today’s Self Help Briefing Affirmation
I trust myself to make choices that honor my values, protect my future, and bring me lasting peace.
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The Self Help Briefing is provided for educational and informational purposes only. Nothing discussed on the podcast should be considered medical, psychological, mental health, legal, or other professional advice. If you have concerns about your physical or mental health, please consult an appropriately qualified professional.
Production Notes
The Self Help Briefing is a production of G Digital Studios. Episodes may be developed from sources available online. Episode artwork may be created using Adobe Firefly or other royalty-free sources. Articles, books, and other resources discussed in an episode are credited and linked in the show notes when applicable. Voiceovers are generated using synthesized audio.









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