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How to Quit People Pleasing and Start Winning at Dating and Relationships

Writer's picture: Anna MorganAnna Morgan

Updated: Nov 7, 2024

Let’s be real—being a people pleaser sounds like it should be a good thing, right? Who wouldn’t want to be seen as agreeable, accommodating, and downright lovable? But when it comes to dating and relationships, people pleasing can actually sabotage your chances of finding genuine connection and happiness. If you’re always bending over backwards to make others happy, you risk losing yourself in the process and missing out on what you really want.


As a dating coach, I see this all the time with clients: nice guys who finish last and kind-hearted women who never get their needs met. People pleasing is more than just a habit; it’s a pattern of behavior that can lead to resentment, burnout, and confusion in relationships. So let’s talk about how to break free from the cycle and start showing up authentically.


People Pleasing

Why People Pleasing Is Happening in the First Place


People pleasing often stems from a deep-seated need for acceptance and fear of rejection. Many people-pleasers have a history of emotional neglect or abandonment, which leads them to believe that they need to keep everyone happy in order to be loved and valued. This behavior becomes a protective mechanism—if they prioritize others’ needs, avoid conflict, and always say "yes," they can prevent people from leaving or getting upset with them. It’s as if their self-worth is tied to how well they can meet others' expectations, making it difficult to assert their own needs and boundaries.

 

Another reason people engage in people pleasing is the desire for approval and validation. Those who grow up in environments where love and attention were conditional—only given when they behaved “correctly”—often develop a belief that their worth depends on others’ opinions. This makes them hypersensitive to disapproval and criticism, causing them to overextend themselves to gain praise and avoid negative feedback. People-pleasers might feel a sense of temporary satisfaction when they make others happy, but it’s a short-lived relief that often leaves them feeling drained, unseen, and disconnected from their true selves.

 

How People Pleasing Harms Your Dating And Relationships


People pleasing might seem harmless, but it’s one of those sneaky habits that can seriously mess up your chances of finding true love. Here’s how it plays out:

  1. Lack of Boundaries: You say “yes” to things that make you uncomfortable or go along with whatever your partner wants, even if it’s not your scene. This sends a message that you don’t have your own preferences and opinions, which can make you less attractive to potential partners.

  2. Emotional Exhaustion: If you’re constantly putting others’ needs above your own, you’re likely running on emotional fumes. This leads to burnout and makes dating and relationships feel like a chore rather than an exciting journey.

  3. Inauthenticity: People can sense when you’re not being true to yourself. Trying too hard to be agreeable can make you come off as disingenuous or wishy-washy. And let’s face it: nobody wants to be with a chameleon who changes colors based on their surroundings.

  4. Attracting the Wrong People: When you prioritize pleasing others over being yourself, you end up attracting people who aren’t a good fit. This often results in relationships where your needs are ignored or, worse, where you feel taken advantage of.

 

How to Break the People Pleasing Cycle


Quitting people pleasing isn’t about swinging to the other extreme and becoming rigid or self-centered. It’s about finding a healthy balance that respects both your needs and the needs of others. Here’s how:


1. Acknowledge Your People-Pleasing Behavior

Start by observing your own patterns. Do you often say “yes” when you really want to say “no”? Do you avoid bringing up things that bother you to keep the peace? Acknowledging these tendencies is the first step toward change.


2. Identify Your True Desires

Spend some time figuring out what you truly want in a partner and a relationship. When you’re clear on your own values and needs, it’s easier to stand your ground when something doesn’t align. This is something you can work through in relationship coaching—whether it’s identifying deal breakers or establishing your dating non-negotiables.


3. Set Small Boundaries

If setting boundaries feels overwhelming, start small. Practice saying “no” to something minor or expressing a differing opinion on a low-stakes topic. With time, you’ll build up the confidence to assert yourself in more significant situations.


4. Reframe Rejection

Understand that saying “no” or asserting your needs doesn’t make you unlikable. The right person will respect you more for being clear and assertive. Rejection, in this case, isn’t a sign of failure—it’s a sign that you’re staying true to yourself and making space for someone who truly values you.


5. Work With a Coach Or Therapist

Sometimes, overcoming people pleasing requires a little outside support. This is where dating coaching or therapy comes in. A dating expert can provide you with strategies tailored to your unique situation and help you practice healthy communication and boundary-setting in your relationships.

 

Real-Life Example


Take one of my clients, Brian, for instance. He was always the “nice guy” who would go out of his way to make sure every date was comfortable, fun, and stress-free—except he never spoke up about his own preferences. As a result, he kept attracting women who were only interested in casual flings, even though he wanted something serious.

Through our coaching sessions, Brian realized that his people-pleasing tendencies stemmed from a fear of being seen as “difficult” or “too much.” We worked on reframing his mindset around conflict and establishing small, meaningful boundaries on dates, like speaking up when he didn’t want to go to yet another rom-com movie. As he started showing up more authentically, his dating life shifted. He’s now in a committed relationship with someone who values his honesty and isn’t afraid to navigate differences together.

 

Breaking free from people pleasing is challenging, but it’s one of the most liberating things you can do for yourself and your love life. As a love coach, I encourage you to take it one step at a time and be patient with yourself. You deserve to be in a relationship where you feel heard, seen, and valued—and that starts by showing up as your true self.


Remember, the most attractive thing you can bring to any relationship is you. 💕


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People pleasing

As a dating coach, relationship coach, and matchmaker, I specialize in guiding singles in breaking through emotional barriers and developing the skills needed for happier, healthier relationships. I offer dating coaching for men and women, matchmaking, empowering dating profile pictures, and dating profile audits for successful online dating. Book a free 30-minute discovery call and learn how your life can be changed.

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