Why do people pleasers struggle with intimacy?

The struggle is real

People pleasers are generally well liked, but not often well loved, at least not in the sense of a genuine connection. Sure, their partner and friends and family might feel like they love them, but if the people pleaser is not being genuine with them, then who is it that they love??

People pleasers will often have a quantity of connections – lots of friends, a string of long term relationships, caring workmates etc. – but they still often feel alone even when surrounded by these relationships.

And people pleasers who are single often struggle to make connections in the first place, finding themselves inexplicably preventing or sabotaging their opportunities even though consciously they believe they are striving to make something happen.

In this post, we’ll explore why people pleasers lack quality connections that are rich, deep and meaningful.


Before we get into this, we need to be on the same page about what certain keywords mean here.

People pleaser: A person who is overly nice and helpful, usually with the hidden agenda of making others feel comfortable and happy so that they’ll like the people pleaser more. What looks like “good” behavior is really more of a strategy to prevent negative judgment, criticism, rejection and conflict. (More on this here).

Intimacy: while people often associate this word with sex, intimacy is really more about emotional connection. Intimate relationships are deep, honest and transparent, where many vulnerable truths have been safely shared and both people feel they can be themselves with each other. 

Avoidant Attachment Style: someone who’s avoidant struggles to let people in, keeping them at arm’s length emotionally so there is no real investment or intimacy that might lead them to getting their feelings hurt by betrayals, break ups and other separations. Also known as an under-sharer or love avoidant.

Anxious Attachment style: someone who’s anxious in their attachments struggles to let people go, is often needy, clingy and desperate, with low standards – they’ll take what they can get and they hold onto it for dear life. Also known as an over-sharer or love addict.

What creates intimacy?

To understand why people pleasers struggle with intimacy, we can look at what is required to make intimacy happen and what’s needed to keep it going.

Honesty is a huge part of it. Both parties need to be equally honest about nearly everything, preferably everything if they can. The more honest they are, the more intimate the connection. More on honesty in this video:

However, this must be reciprocal. If one person is under-sharing and the honesty only goes one way, this is not intimacy. Therefore respect is a huge factor also. Each person must feel safe to share based on the fact that the other person is sharing to an equal depth and quantity.

When you feel like you can predict someone accurately because you know them so well, and you know they feel the same about you, you have an intimate connection.



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How do people pleasers prevent intimacy?

People pleasers usually violate the principles of both honesty and respect, which makes intimacy impossible.

They are rarely honest about their darkness and negativity, despite these being normal human experiences. You only get to see a small slice of the personality pie when you’re interacting with a people pleaser – the happy, easygoing, pleasant stuff.

This automatically creates a respect problem also. Because they aren’t honest, they tend to under-share emotionally, even when it might appear that they’re saying a lot or spending a lot of time with you.

Avoidant people pleasers love to hide behind false-curiosity. They’ll ask lots of questions and explore your life in a show of deep and sometimes genuine interest, but in reality they are using questions to force you to share while allowing themselves to get away with hiding most of their own truth.

More on the manipulative truth of questions here:

In other situations, the people pleaser who has an Anxious Attachment Style will over-share, blurting out all their vulnerable secrets to anyone who is willing to listen. This too violates the respect principle, as the other person is often simply unable to keep up and share to an equal degree. This is also what attracts narcissists and abusers.

Most people pleasers, however, do have at least one or two real connections in their life – an old best friend for example, or a trusted aunt. These relationships allow the people pleaser to see the difference between true intimacy vs. the superficiality of their other connections.

What people pleasers fail to see is that honesty and respect is what created their rare intimate relationships. People pleasers often think they’re only honest with a few people because they feel safe with them. They don’t realize that honesty is what created the safety, not the other way around!

If only they could apply this to other relationships…

Why do people pleasers resist intimacy?

It’s all about fear and trauma. People pleasers had to learn to keep others happy and be seen as a good person to survive safety threats in their childhood.

From overly-critical teachers to emotionally unstable parents to vicious bullies, people pleasers always have a history of feeling unsafe with their connections in early developmental years.

This video covers the common traumas that lead to people pleasing and Nice Guy Syndrome:

The Avoidant people pleasers keep people at a distance through dishonesty, easygoing-ness, humor and pleasantry because in their childhoods they were harmed by people who got in close. Maybe it was always losing best friends due to moving around, or being abused by a trusted family member, or being ‘enmeshed’ by their mother (i.e. emotional incest – the parent treats their child like a partner).

The Anxious people pleasers cling to others because of fear of abandonment. They were left to cry themselves to sleep as infants, or their father walked out on the family when they were 8, or their high school friends would ditch them for no reason.

Intimacy is a source of pain for people pleasers. They are extremely conflicted about people getting in close. And because they attach their self-confidence to other people’s opinions of them, all relationships are inherently threatening.



Get Your Nice Guy Syndrome Diagnosis for Free!

Fill out this quick 2 minute quiz and I’ll give you a personalised Nice Guy Syndrome Diagnosis AND free access to the online course that best suits your current needs and goals. Take the test here:


How can people pleasers get comfortable with intimacy?

Weirdly enough, it’s got very little to do with other people.

The people pleaser really needs to get comfortable on their own. As cheesy and cliched as it sounds, they need to learn to love themselves before they can feel safe letting others in. The Avoidant needs to find validation without needing others to chase and adore them; the Anxious needs to give themselves love without needing others to provide approval.

In more practical terms, they need to take back the power of their self-confidence by shifting away from pleasing others and more towards impressing themselves.

They need to prove to themselves that they can handle getting hurt or betrayed by others, as well as proving that they have the courage to end bad relationships if needed.

People pleasers must learn to build confidence by living consistently by a code of honor, by their core values, in such a way that they eventually come to respect and admire their own behavior. 

A great way to do this that also tackles the intimacy problem simultaneously is to practice being courageously honest – to become shameless. Start showing your dark side, your negative emotions, and your dislikes. Let people feel less than happy in your presence, and learn to navigate those conflicts.

Redirect your energy toward doing what you know is right rather than what is easy and what gets approval from others. Do this enough and you’ll impress yourself, trust yourself, and love yourself, meaning you now have a Secure Attachment and can handle the risks of intimacy.

How you can make massive progress in just a few months!

You can do all this on your own.

Through trial and error, books, courses and online content, you can figure it out slowly piece by piece over time if you dedicate yourself to it and are willing to fail often and get uncomfortable in order to achieve social mastery and build strong self confidence.


You can work directly with me in your corner for a short period of time and achieve the same results in months that would take you YEARS on your own (or your money back!).

That’s what my confidence coaching is really all about. I accelerate your progress significantly by ensuring you:

  • Overcome your fear of rejection
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  • Get advanced practical tips to eliminate self-sabotage and give you the best possible chances at career advancement, dating opportunities, and deep connections with quality friends
  • Help you see your blind spots and errors and develop a measurement system that you can use on your own to ensure ongoing improvement for life

It took me about 7-10 years to figure this stuff out on my own. It takes my average coaching client only about 3-6 months to achieve a level of mastery that leaves them able to continue coaching themselves to further success while feeling absolutely certain that they’re on the right path (proven by the results they get).

I’ve turned virgins into fathers.

I’ve created assertive leaders out of meek people pleasers.

I’ve released overthinkers so they become powerfully decisive.

I’ve transformed shy introverts into social connectors.

I’ve moved highly anxious and depressed guys into a world of permanent self-confidence and optimism.

You don’t need to take my word for it. You can test it out for yourself. Fill out the application form below for a FREE trial coaching session with no obligation to continue, and no sales pitch!

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Thanks for reading

Hope to speak to you soon

Dan Munro

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