Last weekend I was at a coffee meetup where the conversation turned to dating. The question was simple: how do you tell someone after a first or second date that you’re not interested?
Most people admitted they would probably avoid a direct no. Instead they would rather fade out. Delay. Send polite but vague messages until the other person got the gist and gave up.
Then came the contradiction. Almost everyone said they wished others had been clearer with them. It would have saved time, overthinking, and hope that was never going to be realised.
In other words: we want clarity when we are on the receiving end. We avoid it when we have to provide it.
Why drawing a line feel uncomfortable
People rarely draw a line because they don’t understand them. They avoid it because the immediate consequences feel risky: tension, disappointment, awkward silence, being seen as “difficult”.
Even when spoken calmly, informing someone how far you’re willing to go or not can feel like confrontation.
Many people delay a boundary until they can prove it is “reasonable”. They gather evidence, wait for a clearer provocation, or hope the other person will notice. Often that hesitation hides something deeper: fear of being selfish, fear of rejection, fear of the relationship changing.
Past experience or social conditioning may make boundary setting even harder. If conflict felt unsafe growing up, you may have learned that peace requires you to keep your head down and stay quiet. For people from minority groups, being “nice and easy” may have been protective. LGBTQ+ people, immigrants, neurodivergent people, and others who experience scrutiny often carry extra pressure to reduce friction.
A useful question is: Am I choosing this because it reflects my values, or because I’m trying to avoid discomfort?
The cost of not standing your ground
When you repeatedly swallow your needs, you pay in three ways.
First, you teach people your limits are flexible. Not through what you say, but through what you tolerate.
Second, you outsource your self-respect. Your sense of worth becomes dependent on how carefully others treat you rather than on your own standards.
Third, connection turns into performance. You remain agreeable and useful. From the outside it looks like kindness. On the inside it feels like constant self-monitoring.
Eventually the cost shows up as irritation at small things, emotional distance, or an outburst that seems sudden but isn’t.
Setting boundaries without creating drama
In coaching, setting boundaries is a recurring topic. A client may share that someone’s behaviour makes them uncomfortable. We unpack that into: What exactly is happening? What is the concrete impact? What would work better instead?
Clarity usually emerges from that sequence. Once you understand your own position, the words tend to follow.
A boundary is not just a practical request. It carries a message: you matter enough for me to be clear with you, even if it disappoints you a little.
In the dating example: “I’ve enjoyed meeting you, but I don’t feel the connection I’m looking for, so I won’t continue dating.”
Notice there is no long justification and no debate about whether the boundary is justified. It is simply a respectful message that gives clarity without leaving someone guessing.
Short pain, long gain
A clear boundary can feel uncomfortable at first. The other person may push back or test you, simply because the old pattern no longer works for them.
If you are used to accommodating others, this can feel like you’re being unkind. It is not. It is honest. You cannot control their reaction, but you can choose your role.
Over time, the gain becomes clear. Both of you waste less energy on what wasn’t said. Clarity allows you to move on, without frustration lingering. Most importantly, you begin to trust yourself.
There is no need to change everything at once. Start with one recurring situation. Decide what you will no longer agree to, and shape one sentence you can say with steadiness rather than force. If you want to improve how you stand up for yourself in your own context, let’s discuss.
