Episode 408: Do Nice Guys Really Finish Last?

Jun 24, 2025

In this engaging discussion, Caitlin V, a well-known sex and relationship coach with millions of YouTube views, tackles the age-old question of whether nice guys truly finish last. She explains how being overly agreeable can diminish attractiveness and emphasizes the importance of blending confidence with kindness. Topics range from the complexities of the 'nice guy' archetype to navigating sexual desires and boundaries. Caitlin also shares insights on enhancing intimacy and communication in relationships, advocating for authenticity in expressing needs.

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INSIGHT

Beyond Nice Guy vs Bad Boy

The "nice guy" versus "bad boy" is a false binary; attraction involves a mix of traits from both.
Authentic integration of "good guy" qualities and confident "bad boy" traits creates genuine appeal.

INSIGHT

Performative Niceness Hurts Attraction

Some "nice guys" are overly agreeable to avoid discomfort, masking insecurity.
This performative niceness reduces authenticity and undermines genuine connection.

INSIGHT

People-Pleasing Is Manipulation

Excessive people-pleasing is actually a form of manipulation expecting unspoken returns.
This lack of authenticity triggers aversion and undermines healthy relationships.

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You’ve probably heard the phrase before that “nice guys finish last.” But is there any truth to it? That’s what we’re talking about in today’s show. We’re going to discuss how being overly agreeable has the potential to diminish sex appeal, while also interfering with one’s own sexual pleasure. As my guest today likes to say, nice guys need to learn how to say no sometimes.

I am joined once again by Caitlin V, a sex and relationship coach specializing in helping men overcome sexual difficulties. With over 150MM views on YouTube and nearly a million subscribers, she has become a leading voice in the field. Her TV show, Good Sex, is available for streaming now on Discovery+ and Max.

Some of the topics we explore include:

What does being a “nice guy” actually mean?
Do nice guys really finish last when it comes to sex and dating?
How do you walk the line between being confident and assertive in the bedroom without venturing into entitlement?
How can men start to embrace their sexual desires more authentically?

You can check out Caitlin’s website to learn more about her work.

Got a sex question? Send me a podcast voicemail to have it answered on a future episode at speakpipe.com/sexandpsychology.

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Thank you to our sponsors!

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I’m excited to announce a new online course I’m teaching on the topic of fantasies at the Kinsey Institute. Be sure to register for “The New Science of Sexual Fantasies” workshop, which will take place on July 19th, 2025.

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Credits: Precision Podcasting (Podcast editing) and Shutterstock/Florian (Music). Image created with Canva; photos used with permission of guest.