I'm A Chronic People-Pleaser —This One Question Finally Made It Easier To Express My Needs

How to turn frustration into resolution.

Woman sitting down outside, waiting on friends PR Image Factory, TheaDesign,  South_agency | Canva

There was a time in my life when my two best friends shared a common characteristic: chronic lateness.

Even though they’ve never met, it’s like their lateness was in sync. For a while, both of them would reliably be ten to fifteen minutes late for any get-together. They would apologize and give standard excuses. I’d let it go and we’d get on with our plans.

But fifteen minutes began to slip into twenty-five minutes, and then to thirty-five. I was getting more and more annoyed with both of them. I’d use that tactic of giving them a time 15 minutes earlier than I wanted them to get there, and they’d still manage to be extravagantly late.


More than that, they both stopped acknowledging their lateness altogether. They’d just slip into a booth at dinner and be all "Hey! Good to see you! What’s new?" like I hadn’t just waited for more than half an hour for them to show up.

No apology, no nothing.

I noticed my annoyance was changing my behavior towards them. I began to make little passive-aggressive remarks, digging into their soft underbellies, scoring easy, low-blow points. Then I’d leave feeling simultaneously annoyed and self-righteous but also guilty and bad about myself.


It was clear — something had to change.

I wasn’t sure how to bring up the lateness, since I realized just going right in with anger would be counterproductive and make them defensive. But I was angry, and I didn’t feel like tiptoeing around it any longer.

RELATED: 10 Signs You're A People-Pleaser (And It's Sucking The Life Out Of You)

Needing a little feedback, I relayed the situation to my private family Facebook group and asked, how would you handle it?

The answers were fairly predictable from each family member. One said they’d just take it and be angry and never say anything. Another said they’d try a passive-aggressive comment like: "Oh, did you forget your watch … again?" Yet another said they’d just show up even later in a 'Ha! Take that!' kind of approach. A late-off, if you will.


With answers like that it may surprise you that my family is actually fairly functional. But I realized none of these would rectify the situation in a positive way.

Then another family member said they would text something like this:

"Hey, I’m going to ask that you show up on time when we get together tomorrow. You often leave me waiting and I’m sure you can appreciate I don’t enjoy it."

Instantly, I recognized the power of this approach. Simple, relatively easy (low confrontation level), direct, yet also respectful.

I sent each of them that text before our next get-together and I’m happy to report it worked brilliantly. They both replied back apologizing, agreeing it wasn’t a great habit, and continue, years later, to show up more or less on time.


I couldn’t have asked for a more successful outcome.

What struck me with the lateness solution is that I didn’t think of it myself. After years of putting up with bad behavior, somehow it never occurred to me to simply say "Please don’t do this because it bothers me."

While I’m sure men also experience this challenge, every woman knows there’s a gender bias in being able to self-advocate in an assertive manner. The messaging girls and women receive around pleasing others is so overwhelming that we regularly stifle ourselves from addressing transgressions, even when they’re significant.

There was a point at which I fell down from exhaustion at a job and my male boss simply acted embarrassed that I’d shown a sign of weakness. A friend of mine gets a bottle of the same alcohol she hates every Christmas because she wasn’t honest the first year. Another friend didn’t say anything to her doctor when he suggested her husband wouldn’t find her attractive at her current size.


It’s likely none of us seriously considered speaking up because it is so ingrained in us not to. But there are endless challenges to a life where we struggle to set limits. You become the world’s punching bag, doing all the extra work, taking the bad behavior, and never showing your real face to anyone.

RELATED: 16 Signs You're Way Too Nice For Your Own Good

In many ways, I’m an emotionally mature person, but the way I handled the lateness situation, saying nothing and then "punishing" them with unkind remarks, is an area where I’ve got some growing to do. After this incident, I vowed to get better at expressing myself assertively but respectfully.

Of course, it’s much easier said than done. When I feel I need to set a boundary, my gut reaction is to completely withdraw or lash out. These reactions would serve only to communicate my negative feelings, not rectify a bad situation.


This is where the gap between stimulus and response comes in:

"Between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom." — Victor E. Frankel

I tell you, that space is my best friend. When I pull myself away and let myself stew for a while, I’m much better off and can make decisions based on furthering the situation, rather than on serving my hurt feelings. And hey, if I have an immature rant in my head during that space, nobody’s the wiser.

The way that I work out if the dramatics are warranted is by asking myself:

"What would the most emotionally mature version of myself do in this situation?"


This allows me to tap into the part of me that wants resolution, not retaliation. The part that values relationships over ego and being right.

I never fail to chuckle when I ask because the answer is invariably 180 degrees from my knee-jerk response.

But the power of that question is that it helps me to reorient back to the goal — a better solution and ultimately, a stronger relationship.

RELATED: How To Set Healthy Boundaries For Harmonious Relationships

I’ve had the opportunity to use this skillset a few times of late.


I needed to respectfully let Tara, a close relative, know their proclivity for judgmental jabs wasn’t appreciated. It’s tough because I know she’s sensitive. It’s ironic how critical people can’t ever seem to take what they’re so comfortable dishing out.

But after complaining about something I did at her request, I finally decided I needed to say something. I let her know how her comments affected me and also that I’d feel better doing good deeds if they were acknowledged with a thank you.

It caused a little distress as I expected. Tara felt she had a right to weigh in because her comments were apparently borne of concern. It’s an ongoing issue, and one I’ll likely have to reinforce at some point in the future, but progress was made.

I continue to be far from perfect in these matters, but the point is I’m trying and improving. I’ve gotten better at pulling back and taking advantage of that pause.


I’ve almost gotten to the point where I enjoy having the opportunity to exercise this skill. Self-advocating is like a muscle, you strengthen your abilities every time you use it.

Interestingly, you also strengthen your relationships. People don’t like boundaries but there is something about going through that kind of heightened discussion that results in deeper respect and understanding.

Who knows? I may come to the point where I look forward to it. But I doubt it.

RELATED: 10 Warning Signs You're Letting People Walk All Over You

Ellen Eastwood is a freelancer, pop-culture enthusiast, and contributor to Yourtango.