Why Do I Overthink Every Relationship? Therapist Shawna Tiles Answers

An Ontario therapist explains why people replay conversations, seek reassurance, avoid conflict, and lose confidence in their own decisions.

You send a text message or leave a conversation with someone. Then the analysis begins.

Did I say too much? Did I sound annoyed? Are they upset with me? Should I explain what I meant?

By the time the other person responds, you may have constructed several explanations, reconsidered what you said, or drafted a follow-up message you are unsure about sending.

Overthinking in relationships can affect dating, friendships, family relationships, and work. It can make feelings of uncertainty feel urgent. It can also lead people to not voice what they need, avoid difficult conversations, or rely on reassurance from others that doesn’t seem to last.

This is the special interest of Shawna Tiles, a Master of Arts in Marriage and Family Therapy graduate and Registered Psychotherapist (Qualifying). She studies why these patterns develop and what helps people respond differently.

Shawna works with people who struggle with overthinking, people-pleasing, relationship stress, self-doubt, and difficulty trusting their own decisions.

Her marriage and family therapy education gives her a strong understanding of how attachment, family experiences, expectations, and roles in relationships influence the way people respond to conflict and feelings of uncertainty. She is passionate about working with people who are highly aware of everyone else’s feelings and have gradually lost confidence in their own.

In this interview, Shawna explains:

– Why people replay conversations
– How people-pleasing fuels overthinking
– Why reassurance rarely settles the worry for long
– How to separate evidence from assumptions
– What therapy for relationship overthinking involves
– How to decide whether Shawna may be the right therapist for you.

You can also find Shawna sharing practical mental health and relationship content on TikTok at @shawnatilespsychhttps://www.tiktok.com/@shawnatilespsychotherapyotherapy, and follow her Facebook Page @shawnatilespsychotherapy

Erika: Shawna, I’m excited to share about your passion and expertise. Tell me, when someone says, “I overthink every relationship,” what are they usually experiencing?

Shawna: Relationship overthinking often happens when someone has become highly attentive to other people’s moods, reactions, or approval. Their brain analyzes the hidden meaning behind conversations and small changes in behaviour because it has experienced emotional unsafety and is trying to protect them from conflict, rejection, or disappointment.

This can look like replaying what a person said, trying to make sense of someone’s tone of voice, wondering whether someone is upset, or trying to predict what will happen next. Overthinking often happens when you recognize that your worry is disproportionate to the situation and still find it difficult to stop the pattern of thought. 

For many people, this pattern developed gradually. They learned that paying close attention to others may have helped them maintain close connection, reduce conflict, or understand what was expected of them. What can make it difficult, is that the awareness of what others might be thinking and feeling and continues even when there is no external pressure or sense of urgency.

The person becomes very skilled at reading everyone else while feeling increasingly uncertain about their own thoughts, feelings, and needs.

Why Do I Overthink Every Relationship?

Erika: So overthinking can feel like problem-solving?

Shawna: Yes, in a sense. It can feel like you have to be responsible and productive because you are constantly thinking through every possibility. It can feel like your brain is always on overdrive. And most of the time, the analysis does not produce useful new information because it’s a repetitive cycle in the brain that doesn’t interact with new information from the external world. The overthinking only creates more possible explanations and more uncertainty.

A helpful question is:

“Am I learning something new, or am I reviewing the same information because I want certainty?”

That distinction can help you recognize when reflection has shifted into an overthinking cycle.

Key takeaway: Overthinking in relationships is often an attempt to create certainty, prevent conflict, and protect connection. Therapy can help you respond to uncertainty without repeatedly analyzing yourself or the other person.

Distinguishing overthinking from a relationship problem

Am I Overthinking, or Is Something Actually Wrong in My Relationship?

Erika: How can someone tell whether they are overthinking or responding to a real relationship problem?

Shawna: It helps to start with observable facts. Ask the person, what happened, what was directly communicated, and notice whether the concern is based on a repeated pattern or one moment.

A relationship concern may be supported by repeated behaviour, broken agreements, dismissive responses, inconsistent communication, or an ongoing difficulty that remains unresolved after it has been openly talked about.

Overthinking usually produces a list of possibilities. You may move from one explanation to another without receiving any new information. Even reassurance from the other person may bring relief for only a short time before another doubt emerges.

Overthinking and genuine relationship concerns can also happen together. A person may have a valid concern and also become caught in hours of analysis while trying to determine exactly what it means.

Erika: What questions can help someone sort through that?

Shawna: I would ask:
– What directly happened?
– What meaning might you be assigning to what happened?
– Could this be part of a repeated pattern?
– Have you sought clarification from the other person?
– How did they respond when you expressed the concern?
– Are you gathering useful information or seeking to eliminate every possible uncertainty?

The goal is to identify what you actually know, what you are assuming, and what may require a direct conversation.

Erika: What if someone still can’t tell between them?

Shawna: That is a useful reason to meet with a therapist. Therapy can help you explore the situation in a safe space without pressure to make a decision on the relationship. You can look at the patterns, your emotional response, your relationship history, and the patterns influencing how you interpret uncertainty.

Key takeaway: Separate the event from the meaning you have assigned to it. Look for repeated patterns, direct communication, and how the other person responds when you express a concern.

How Are People-Pleasing and Overthinking Connected?

Erika: Many people who overthink their relationships also describe themselves as people-pleasers. How are these two characteristics connected?

Shawna: People-pleasing often can cause other people’s reactions to feel like your responsibility. You may believe that maintaining the relationship depends on saying the right thing, avoiding disappointment, or making sure everyone is comfortable.
That puts a lot of pressure on the self to analyze others.

You may replay a conversation to assess how you came across to others, and whether you sounded rude. You may reconsider a boundary because the other person seemed disappointed. You may explain yourself repeatedly because you want to prevent anyone from misunderstanding you.

Overthinking becomes a way of trying to manage the relationship before anything goes wrong.

Erika: Can setting a boundary create anxiety?

Shawna: Yes, a boundary introduces the possibility that someone may disagree, feel disappointed, or respond differently than you had initially hoped. For someone who has learned to maintain connection through the accommodation of others, that discomfort can feel like evidence that the boundary was wrong.

They may begin thinking:
– Was I too harsh?
– Should I have explained more?
– What if they think I am selfish?
– Should I take it back?

The discomfort that follows a boundary does not automatically mean the boundary was inappropriate. Sometimes it just means you are doing something unfamiliar.

Erika: Can someone stop people-pleasing without becoming uncaring?

Shawna: Of course. The work involves making room for your needs alongside the needs of others. You can remain thoughtful and considerate while communicating honestly, making decisions, and allowing other people to have their own reactions.

Therapy can help you build enough confidence in yourself to tolerate disagreement without immediately abandoning what you need.

Key takeaway: People-pleasing fuels overthinking when you feel responsible for preventing disappointment, conflict, or misunderstanding. Healthier relationships allow room for honesty, boundaries, and different reactions.

Related support: Learn more about online therapy for overthinking, people-pleasing, and relationship stress in Ontario with Shawna.

Why Does Reassurance Help for Only a Short Time?

Erika: How can someone receive reassurance and still begin worrying again shortly afterward?

Shawna: Reassurance often answers one specific fear without changing the pattern that created it. You may feel better when someone says they are not upset, the relationship is fine, or you did nothing wrong. But that often isn’t the core of the problem, so then your mind finds another detail to question.

You may begin wondering whether they meant what they said, whether their tone sounded different, or whether they were trying to avoid a difficult conversation.
The relief is real. It is also temporary because your confidence is still dependent on receiving assurance from someone else.

Erika: Can reassurance-seeking strengthen the overthinking cycle?

Shawna: It can. Each time anxiety is resolved through immediate reassurance, your mind learns that uncertainty requires an urgent answer. The next uncertain situation may feel even harder to tolerate without checking.

This does not mean you should never ask questions or seek clarification. Healthy relationships involve communication. The useful distinction is whether you are gathering information that helps you respond or repeatedly asking for clarity that no one can fully provide.

Erika: What can someone do before asking for reassurance to ensure its for healthy reasons?

Shawna: Pause and ask:
– What am I afraid this situation means?
– What evidence do I have?
– Have I already received an answer?
– Is there new information to discuss?
– What feeling am I trying to make disappear?
– Can I allow some uncertainty before taking action?

The aim is to become more capable of evaluating your own experience and deciding when a direct conversation is genuinely needed.

Key takeaway: Reassurance can settle one fear temporarily. Lasting change involves building confidence in your own judgment and increasing your ability to tolerate ordinary relationship uncertainty.

Why Do I Struggle to Know What I Want in Relationships?

Erika: Some people can identify what everyone else wants but have trouble answering, “What do I want?” Why does that happen?

Shawna: When you spend a lot of time adapting to other people, your attention naturally moves outward. You become skilled at noticing expectations, moods, preferences, and possible reactions.

Your own preferences may receive attention only after you have considered what will be easiest, safest, or least disappointing for everyone else.

Eventually, even ordinary decisions can become difficult. You may know what your partner, parent, friend, or employer would prefer while feeling uncertain about your own answer.

Erika: Is that why some people need other people to approve their decisions?

Shawna: It can be. External approval may have become the signal that a decision is acceptable. When approval is unavailable, the person may continue researching, asking for opinions, changing their mind, or delaying the decision.

The problem is rarely a lack of intelligence or insight. The person may have had limited practice making choices while allowing someone else to disagree.

Erika: How does therapy help someone reconnect with their own preferences?

Shawna: We begin by slowing the decision down and separating several questions:
What do I think?
What do I feel?
What do I need?
What do I prefer?
What am I afraid someone else will think?
What choice fits my values?

The in-session work then becomes practicing making manageable decisions without collecting excessive opinions or preparing a defence for every choice.
Self-trust develops through experience. You make a decision, respond to the outcome, and learn that uncertainty or disagreement does not automatically mean you chose incorrectly.

Key takeaway: Knowing what you want becomes harder when every decision is filtered through other people’s expectations. Therapy helps you recognize your preferences, make values-based choices, and tolerate disagreement.

How Does Therapy Help With Overthinking in Relationships?

Erika: What happens in therapy for someone who overthinks relationships, seeks reassurance, or struggles to communicate what they need?

Shawna: In the virtual therapy room, we begin by understanding the pattern in detail. We look at what triggers the overthinking, the meaning you assign to the situation, how your body and emotions respond, and what you do next.

A pattern might look like this:
– Someone responds differently than expected.
– You assume you have done something wrong.
– You replay the interaction and search for evidence.
– You seek reassurance, withdraw, apologize, or overexplain.
– You feel temporary relief.
– The uncertainty returns.

Once the pattern is visible, we can work on changing specific parts of it.

Erika: What might clients practice in therapy?

Shawna: Depending on the person, therapy may involve:
– Recognizing emotional triggers earlier
– Separating observable facts from assumptions
– Identifying feelings, preferences, and needs
– Tolerating others uncertainty before reacting
– Communicating concerns more directly
– Setting boundaries without excessive explanation
– Making decisions with less external reassurance
– Understanding how family and attachment patterns influence current relationships

I draw from attachment-based therapy, Motivational Interviewing, Emotionally Focused Therapy, Strengths-Based Therapy and values-based approaches. The methods depend on the client’s goals and the patterns affecting their relationships.

Erika: Does someone need to attend therapy with their partner to work on their relationship?

Shawna: No. I provide individual therapy. A client can work on their own overthinking, boundaries, communication, and decision-making even when the other people in their life are not involved in therapy.

As clients respond differently, they often gain clearer information about their relationships. They can communicate more honestly, notice which relationships allow room for their needs, and make decisions with greater confidence.

Key takeaway: Therapy helps you understand the full overthinking cycle and practice new responses at the points where anxiety, assumptions, and reassurance-seeking usually take over.

Erika: Thank you for taking the time to tell us about your practice, your approach and the area that you are passionate about.

Shawna: You’re very welcome!

Think Shawna May Be a Good Fit?

Shawna provides online individual therapy for adults and young adults throughout Ontario. She works with overthinking, people-pleasing, relationship stress, self-doubt, and difficulty trusting your decisions.

Learn more about therapy with Shawna or book a free 20-minute consultation.

Meet Shawna

Shawna Tiles is a Registered Psychotherapist Qualifying who works with young adults and adults struggling with overthinking, self-doubt, people-pleasing, relationship stress, and life transitions.

Clients often come to Shawna feeling stuck between what they need and what they believe others expect from them. Together, they explore patterns that create anxiety, uncertainty, and emotional exhaustion while building greater confidence, self-trust, and clarity.

Shawna’s approach is warm, collaborative, and grounded in helping people reconnect with their own voice.

Book A Free Consult With Shawna