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How To Stop Pleasing People But Still Be Nice (In Dating)

How To Stop Pleasing People But Still Be Nice (In Dating)

How To Stop Pleasing People But Still Be Nice (In Dating)

Even before she finishes the request you feel your lips beginning to take form in the shape of a yes.

People-pleasing has become such a part of your identity that it’s now a knee-jerk reaction to requests.

You have a habit of appeasing people when in work, social, and romantic settings — but enough is enough.



You’re here to take back your autonomy and to start looking out for number one without coming across as callous.

Since 2012 I’ve been helping men achieve their romantic goals with my coaching and matchmaking services. During this odyssey I’ve worked with my fair share of people-pleasers.

If there’s one dynamic that brings out a people pleaser’s toxic habits more than any other, it’s that of a fledgling romance.

The fear of losing someone else and being rejected has a way of amplifying unhealthy behavior.

In this article, I’ll provide you with 7 actionable ways that will teach you how to stop pleasing people you’re dating.

How To Stop Pleasing People (While Dating)

Just because you’re working towards no longer putting another person’s needs ahead of yours even when it’s a detriment to your own well-being doesn’t mean you’re suddenly going to turn into a monster.

Aspiring to not please people doesn’t mean you’ll suddenly treat everyone like a rude snob.

It means you’re prioritizing your own happiness.

Being kind to yourself doesn’t mean you’re being rude to someone else. 

Let me show you what I mean.



1) Do Not Go On Another Date If You Don’t Really Want To

If you’re single and MegaDating it means you’re going out with a ton of women in a short period of time.

As much as you’d like to never break up with these women at some point you’re going to have to reject one or two of them.

If not you’ll only end up hurting the both of you as you continue to invest time, money, and emotion into a relationship that already has an expiration date.

If you no longer want to see this person you can simply not message them after a date.

However, not all women get the message.

Some will poke and prod until you ask them out again.

If this is the case you’ll have to fight the urge to succumb to their desires.

Do so by letting her down easily.

Write them…

“It’s been nice getting to know you but to be transparent, I’m just not feeling the chemistry that I need to move forward. I hope you understand and wish you all the best.”

If even this sounds too harsh for you, text her…

You’re funny and intelligent, and a whole bunch of other amazing things but we’re just not compatible. I want to respect your time and let you know that it’s best if we see other people.”

Reframe the interaction so you don’t feel like the bad guy.

The evil thing to do would be to continue to see her all the while knowing it isn’t going anywhere.



Treating her right sometimes means hurting her in the short term.

2) Set Strong Boundaries for Your Dealbreakers: How To Stop Pleasing People

We all have dealbreakers or at the very least things that really turn us off.

Here’s an example:

She knows you’re 6 months sober but casually mentions drug use on the regular.

Naturally, this would be a pretty big deal-breaker for you.

Yet your initial urge is to make excuses for her and not make waves.

 Just because you don’t want to hurt her feelings is not the reason to continue dating her if your values and life choices strongly diverge.

Make a list of your dealbreakers.

Thinking long and hard about no-nos will make it easier to not only identify them but to end things with a woman when they present themselves.

Put them on a sticky note or index card and carry it in your wallet.

If you find yourself in a relationship with a woman who meets one of those qualifications for “dealbreaker” check your index card and either address the dealbreaker or let the woman go. 



Having boundaries/higher standards is a must for people-pleasers who often find themselves in relationships that are unfulfilling or at worst, outright damaging to their health and well-being.

Pro-tip:

Try and uncover these deal-breaking qualities before the third date and most certainly before sex, when people can become overly attached and have a harder time recognizing red flags.

While you may be able to accept a wider range of people in life, the one person you’ll ultimately accept as your life partner needs to have a stricter, more selective criteria.

You can’t allow just anyone in.

3) Know When To Friendzone

Be honest and kind — but direct and resolved.

If you don’t feel chemistry with a woman you enjoy hanging out with it’s better to say so, rather than linger and see if your feelings change.

Your body knows the truth.

Don’t be afraid to communicate that.

It’s far kinder to let someone know you’re not feeling it than it is to string them along.

Here’s a template to help you out…

“Hey Jen. So you’re awesome and I while I don’t think we’re romantically compatible I do think we’d be great friends. Let me know how a more platonic relationship works for you. I’d still love to go hiking with you this weekend.”

The formula here is simple:

Compliment + realization + invitation to hang in the near future. 



This not only lets her down easily but uses enough tact to ensure that your romantic interest remains your friend.

4) Set a Time Boundary on First Dates

You’re a nice guy.

Perhaps too nice.

It’s for this reason you typically ask women you don’t know very well on extravagant first dates.

You promise the moon to someone you’ve never even seen before.

While this is a way to sweep a woman off her feet it also ensures you spend all your money on a woman you’ll never see again.

To guard against throwing the bank at a woman you may dislike the second she sits down on that suede cushions at that fancy Brazilian buffet you invited her to, we need to set some ground rules.

First dates should:

  • Last no more than one hour
  • Cost no more than $10

Chances are you met this person online (that’s how most relationships are started nowadays).

why do my dates never work out

So for all intents and purposes, she’s a stranger.

I ask you.

Why sign up to spend $100+ dollars and your entire Saturday night with a complete stranger?



Just because it’s a date doesn’t mean you need to play by old-school dating rules.

Manage both your and her expectations upfront by asking her out on a date that lasts no more than an hour and is next to free.

If you’re struggling to come up with awesome first ideas, I have a few ideas for you. 

5) If You’re MegaDating, Set A Limit for How Many Dates You Can Go On Each Week

Once you get in the habit of MegaDating you’ll notice that scoring dates isn’t all that difficult.

Your calendar will quickly fill up with dates.

The thing is, once you start MegaDating you fall under a spell of sorts.

how to stop pleasing peopleYou follow a certain script, say the right things to women online, get their number and use a TDL to ask them out.

Soon enough getting a number and asking a woman out becomes automatic.

After learning to MegaDate, clients of mine (and maybe you next) often come to me and say “Em, I have too many women responding to me and not enough time to date all of them, what do I do?”

This is exactly the problem I want them to have.

But at some point, you’ll have to turn the faucet off.

Once you have more women to date than time allows for choose the two women you’re most excited about.



In this way, the cream naturally rises to the top and you get crystal clear on who your most ideal type of woman is.

With plenty of options to choose from, settling becomes a thing of the past.

You can also keep the other women as “warm leads” and nurture the connection in case you end up not vibing well with one of the other women.

This way, you never have to spend another weekend alone but you’re also not so slammed with dates that you can’t remember their names.

6. Set a Cost Boundary on First and Second Dates: How To Stop Pleasing People

Early on in a relationship, it’s far too easy to overspend on your new fling.

In your attempt to make the very best impression possible you end up splashing out the cash.

Spending too much money too soon is out of sequence and either attracts gold-diggers, gets you friend zoned, or raises her standards to a ridiculous level. 

In my program, I teach my clients to select first date locations that won’t cost you more than $10 dollars and select second date activities that are free.

When you set this boundary, you eliminate women who are more interested in what you can do for them than in who you are.

Doing so subconsciously demonstrates that you’re high-value because your money is hard to get, and therefore, so are you.

7.) Don’t Budge If Your Date Wants to Do Dinner Instead of Coffee

This is all-too-common and it causes a lot of people pleasers to cave in and just do what the woman wants.

Based on my 100-date experiment, dinner dates on a first or second date are the kiss of death.

You want to make her work for it.

Dinner dates are out of sequence if they happen early on because too much time and money are exchanged too soon and it causes the woman to perceive you as lower value.



The trick to the first date is to leave her always wanting more so you have mystery, which breeds sexual tension.

When she tries to call an audible, tell her…

“I don’t do dinner until a third date. If we make it that far, I’d be happy to take you to dinner.”

It’s sexy when a man has boundaries and says “no” gracefully and will increase her perceived value of you. Women love men with boundaries.

This will also prevent you from wasting money on women you won’t ever see again.

How To Stop Pleasing People Wrap-Up

There is no magic switch that will show you how to stop pleasing people when dating.

These tips are just the tip of the iceberg when it comes to changing your ways.

The absolute best way to stop being so accommodating is by filling up your social calendar with dates and interacting with loads of new women.

Doing so will boost your confidence and quickly give you the skills you need to say no and start advocating for yourself.

To learn more about how you can MegaDate, let’s chat via a 1-on-1 Zoom session. During the session, I’ll learn more about your goals and show you how my program can help you achieve them.

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