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Caitlin's Couch · May 8, 2025

Toxic People Pleasing

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Tips for recognizing when people-pleasing is harming you and what to do about it.

woman in black and white stripe dress holding wine glass
Photo by Zachary Kadolph on Unsplash

POST SUMMARY

People pleasing isn’t always a bad thing. In a healthy relationship, it feels good to please our partners. When we go out of our way for them and it makes them happy, it also makes us happy. It becomes unhealthy when no matter what you do, they’re never pleased, or if you measure your worth based on pleasing others, or if you consistently abandon yourself for someone else. This post will show you how to be a healthier people pleaser. You’ll learn:

  • How to recognize when your desire to people please is unhealthy for you

  • What to do instead

  • How to elevate your self-esteem without needing approval from others

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THE POST

My mom once had an aide named Lucy who seemed really cool. She was friendly, funny, and helpful. Over time, however, I noticed that Lucy took time off whenever I visited my mom. At first, I thought she wanted time off when I was there, so my mom wouldn’t be alone. But helping my mom and taking care of my family was a lot for me, so I decided to ask my mom about it.

My mom hadn’t noticed the pattern, but when I pointed it out, she decided to talk to Lucy about it. The problem wasn’t just that it was hard on me to take care of everyone, but also, my mom couldn’t spend time with Gabby (my daughter) without Lucy there to help. Gabby and my mom wanted to spend time together, so Lucy needed to be there for our visits.

After speaking to Lucy, my mom found out that Lucy didn’t like being there when we visited. She said there were two reasons. First, she didn’t want to be a babysitter. Second, it bothered her that we were messy. My mom told her she needed help to take care of Gabby, and that was a non-negotiable for her. If Lucy wanted the job, that was part of it. It was only a couple of times a year, so Lucy conceded (round of applause for my mom setting a boundary👏).

While Lucy’s attitude toward my daughter bothered me, I put those feelings aside because my mom is hard to please, and their relationship was mostly good. I didn’t want to come between them.

As far as being messy, I agreed with her. I fully admit that being neat and tidy isn’t my strong suit and never was. So, I agreed to be less messy and to honor her specific requests for how she wanted things done while we visited.

During our next visit, I was a temporary neat freak. You couldn’t tell that there were three additional people in the house. My mother commented on how shocked she was, and my husband said he didn’t know I had that in me. I was careful to put the towels where she wanted them, not to leave a dish out, and to make sure everything was exactly as we’d found it.

Then, on the last day of our visit, my daughter was playing and made black marks on the floor. Lucy, exasperated, said, "Look at those marks on the floor!” and ran into my mother’s room in a tizzy to tell her about them. I jumped up, worried the marks were permanent because Lucy was so upset, and began wiping them up. They came out easily. That’s when I realized that Lucy was an unpleasable person.

Trying to please unpleasable people is a painful journey that never ends. No matter how hard you try, it’s never enough. Eventually, resentments build, you abandon yourself more and more, and your self-esteem takes a nose dive.

Once I realized that no matter what I did, Lucy would find something to complain about, I stopped trying so hard. I felt sad about it. I wished she weren’t so unhappy when we visited. I could have let my sadness lead me to work even harder next time, but there would always be something. So instead, I let myself feel sad and didn’t try to fix it. Then, I got clear on what I thought was right in the situation. I wanted to be the kind of guest who I’d want in my own home. Going forward, as long as I met my own standards and did what aligned with my values, I felt good about it and good about myself. When Lucy complained, I let it go in one ear and out the other. I chose to make my own voice the loudest, not hers.

From then on, I felt more relaxed on our visits because I knew my standards and could meet them. If I continued trying to please Lucy, I’d feel anxious, never knowing where she’d move the goalposts.

Unpleasable people complain because that’s how they are. It’s a thought pattern and a habit for them. Someone who finds things to complain about or criticize will always find those things. That’s why it’s important to stop taking it personally.

If you’re a self-proclaimed people pleaser, make sure you’re not trying to please someone who is never satisfied. If you’re in a relationship where you never feel good enough—this could be your partner, parent, boss, friend, etc—there’s a good chance the problem is the person you want to please, not you. The first step in changing this painful dynamic is to recognize it. If you realize that you can’t please the person no matter how hard you try, get clear on your own standards. If they criticize you, think about whether or not you agree with their point. If you do, let it inform you of your own values and change the way you do things going forward. If you disagree, keep doing things your way. No matter what, don’t let their criticisms inform you of your worth. Your worth isn’t in question, nor is it dependent on what this person thinks of you or getting their approval. Remember, only you have the power to define your worth.


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