Anxiety Therapist in Chicago, IL -When “Nice” Turns Toxic: People Pleasing, Anxiety, and Dating Again

As an anxiety therapist in Chicago, IL, I often see how people-pleasing shows up in dating and relationships. On the surface, saying “yes” to someone when you really NEED to say “no” may feel like keeping the peace or not being seen as mean. But in actuality, it can create so much anxiety, resentment, and exhaustion — especially when you’re dating again after a breakup or divorce.

If you’ve been in a relationship before and it ended for various reasons, it could be very scary and overwhelming to go out on dates again. They ask:

• “How do I know I’m ready to date again?”

• “Am I being too picky—or not picky enough?”

• “What if I mess this up again?”

• “ I don’t want to be in another codependent relationship again.”

Here’s the truth:

You don’t have to do anything that you’re not comfortable doing, regardless of who you are. We all want to be seen and accepted in our relationships. The more we can focus on taking care of our needs, wants, and expectations in a relationship, the more clarity we will have in finding someone who will be compatible with us.

In this blog, I want to help you reflect on:

• Why people pleasing becomes a survival tool in relationships

• How anxiety can cloud your ability to trust yourself in dating

• And how you can build self-worth and connection, not just by being “nice,” but by being real

Let’s Pause and Reflect

Grab a notebook, a pen, and an open mind as we dive into how to talk about how to stop abandoning yourself—and how to date again, with courage, clarity, and confidence. Before we get started, here are a few questions to consider. If you find yourself nodding along to these questions, I’d love to connect—use the link below to book a free 15-minute Zoom consultation.

• What are you hoping to get out of dating again?

• Are you dating because you want to connect - or feel like you should?

• What are your dealbreakers and expectations for how you want to be treated in a new relationship?

Why People Pleasing Feels Like the Only Option

People pleasing might be the only option if it’s the main way you receive love or attention from others. That’s not a bad thing. If you’ve grown up in a home environment where you’ve had to re-adjust often, whether it’s your schedule, silence your voice, or needs for others - you’re not alone. We may unconsciously repeat the same behaviors, lessons, and reactions that we’ve seen in the people who raised us.

Silencing Yourself

• Grew up where emotions were dismissed or seen as a weakness

• Kids were expected to be “seen, not heard”

Guilt and Self-Sacrifice

• Saying “no” = “disrespectful” or “selfish”  

• You minimized your own needs to avoid being a burden

Learning Self-Neglect From Role Models

• You watched adults around you overwork, over-give, and ignore their own limits

• You absorbed those lessons to be a “good person” that’s what you must do

Questions to consider:

• When did you first learn to be “nice” to protect yourself from getting hurt or disappointing others?

• Whose approval are you looking for, even if they are not in your life anymore?

• What are you afraid might happen if you stop saying, “yes” or being the one who smooths things over?

The Hidden Anxiety Beneath People Pleasing

If you were nodding along to the lessons above, it may be no surprise to see that dynamic being re-created in your other relationships, especially with a significant other. Maybe in your previous relationship, there were many signs that you were co-dependent on your partner, that you might not have realized were unhealthy. Do you recognize any of these?

• Avoiding conflicts whenever necessary

• Lack of interest in engaging in hobbies, or seeing friends/family

• Fears of disappointing your partner, being abandoned, or rejected

• Erasing your identity, values, and beliefs because it doesn’t align with theirs

• Feeling angry, resentful, and distant

Questions to consider:

• When was the last time you noticed yourself saying yes when you actually meant no?

• Do you feel like your needs are too much for others? Where do you think that belief came from?

• What does rejection mean to you—and is it always personal?
  

Dating After Abuse or Loss: Why People Pleasing Intensifies

When you’ve been deeply hurt in love, people pleasing often shows up louder than ever—because deep down, you don’t want to risk that kind of rejection again.

If you’ve ever experienced heartbreak, you know how devastating it can be when a relationship that you believed would last forever ends. That pain may make you feel so afraid of starting to date someone again. Maybe this ex-partner made you question who you are, convincing you to believe that you are not worthy of love and respect. They might have also made you feel physically or emotionally unsafe, time and time again.

It might have taken so much courage - and support - to leave a toxic relationship. You might remember how often you made excuses for your partner before finally deciding that you don’t want to walk on eggshells any longer. Saying, “no more,” was the first step to starting over.

Now, as you begin to rebuild your relationship with yourself, you may be carrying doubt from all of the times you second-guessed your worth. Or, on the other end of the spectrum, you might feel anger - resentful of the time wasted on someone who didn’t deserve it.

And when you finally decide to date again, it’s natural to be on guard. No one would fault you for that. Your nervous system may be in overdrive because it remembers how your ex treated you. People pleasing may be the safest way for you to avoid rejection or abandonment happening again. 

Questions to consider:

• How have past relationships shaped what you now believe about yourself?

• What are some red flags you ignored in the past—and what would it look like to honor those signs next time?

• What would it mean to feel emotionally safe in a relationship again?

Optional exercise:

Write a letter to your past self, to the version of you who stayed too long in an unhealthy relationship. What do you want them to know now?

How an Anxiety Therapist in Chicago Helps Rebuild Boundaries

I’ve written a blog post that can help you rebuild your boundaries, that you can read here. However, here are a few reminders:

• Pause before you answer the text or in conversation with someone in person

• Say something like, “Let me think about that and get back to you.” 

• Practice saying “no” in less stressful settings  

• Check in with yourself on how you would like to respond to what someone is asking from you

• Saying “no” is a statement, and you do not owe anyone an explanation or overly explain why you cannot do the thing they’re asking you to do. You don’t have to be mean or rude. You can validate their frustrations, but know that you are allowed (I give you permission, if you don’t do that for yourself!)

Questions to consider:

• Which relationships in your life feel the most draining—and what patterns do you notice?

• What’s something you did recently that didn’t feel aligned with your values, but you did it to keep the peace?

• Do you believe your needs matter just as much as someone else's?

Building Confidence to Date as Your True Self

Before jumping into a new relationship or going on your next date, try taking yourself on a date first and notice what that feels like for you. While you’re there, pay attention to what comes up - do you reach for your phone to fill the silence, or feel uncomfortable with the weird looks from others?

This is an opportunity to get to know yourself on a deeper level. Explore what you truly value, what brings you joy, and what you would like to contribute when you’re with a partner. You may even remember old interests or friendships that were dropped from your priority list. Now is the perfect time to reconnect!

The more you rebuild your sense of self, the more likely you will attract someone who’s naturally compatible with you.

Optional Challenge:

Before your next date, write down 3 values that are important to you in a partner—and 3 ways you embody those values yourself.

Final Questions to Consider:

• What would change in your dating life if you stopped striving to be “nice” and instead focused on being real?

• What small shift can you try this week to reclaim your voice or needs in a conversation?

• Are you willing to get to know yourself better—before asking someone else to do the same?

  If people-pleasing has left you feeling anxious, drained, or unsure of yourself in relationships, you don’t have to keep repeating the same cycle or do it alone. As a therapist for people-pleasing and boundaries in Chicago, I help clients find their voice, set limits without guilt, and rebuild confidence in dating and beyond so that they feel more grounded in themselves. I offer online therapy for anxiety in Illinois, so you can access support from wherever you are.

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