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

how to stop pleasing people when 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 my team and I have been helping men achieve their romantic goals with my coaching 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, students 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 students 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.

10 Examples Of Approval Seeking Behavior In Dating (+ How To Drop Your Need For Validation)

approval seeking behavior

It’s natural to seek the approval of those we love most.

We’ve been doing it ever since we were children trying to win our parents’ affection.

But sometimes approval seeking behavior goes a bit too far. Sometimes it veers off into unhealthy territory.

Approval seeking behavior that sees us sacrifice parts of ourselves in an attempt to win the approval of others is objectively unhealthy. This behavior most often manifests in our romantic relationships.

In an attempt to mitigate this behavior we’re going to identify the 10 most common examples of such behavior in a romantic relationship.

But identification is only half the solution. After we’ll give you a blueprint you can implement to address your reliance on others for your self-esteem.

10 Approval Seeking Behaviors

Again, everyone changes their behavior to win the approval on someone else — but to a degree.

If you identify with a couple of these behaviors you may have nothing to worry about. However, if you identify with at least 50% of these behaviors you may want to consider changing your dependence on your partner with validation.

1) Laughing At Literally Everything

Hahahahaha.

Wait, I didn’t say anything.

Laughter is an age-old response that we use to connect with someone. Laughter is one of the easiest ways to seek and often win the approval of another. Have you ever noticed yourself laughing more often than usual when meeting someone new?

It’s because laughing with someone or at another’s joke is a relationship accelerant.

On the contrary, don’t you find it odd when someone just smiles or never laughs at a joke? We intuitively know this is a clear indication they don’t wish to bond.

Laughing is one of the more harmless approval seeking romantic behaviors there are. But if you’re doing it more often than your partner this may be a signal of an emotional imbalance.

You may like them a lot more or rely on their approval much more than they rely on yours.

approval seeking behavior

2) Pretending To Agree

Yeah, that pasta your partner made is amazing, and yeah of course you love Fast And Furious, yeah totally the USA is as much to blame as Russia for the way… wait what?

Listening, empathizing, and understanding a conflicting opinion isn’t a sign of people-pleasing. Vehemently agreeing with everything your partner says, however, surely is.

White lies and agreement are acceptable. Agreeing their parents are good cooks, or that your friend’s band is worthy of recording time in a studio is one thing. These white lies are meant not to hurt your partner and you’re telling them so that they aren’t hurt.

Pretending to agree however when it comes from a place of approval-seeking is very different.

3) You Always Say Sorry

You say sorry more often than a Canadian that actually owes an apology.

Except you apologize when something isn’t your fault.

Stop apologizing for the weather, the quality of the road, or how undercooked their burger was.

These are things out of your control. Don’t blame yourself or allow yourself to be a scapegoat for all the ills of the world. Saying sorry all the time is actually not an attractive quality. Even though it at times may come from a good place, it’s a bad habit to get into.

You’ll be looked down upon by others and will open yourself up to manipulation.

4) You Always Say Yes

You believe the easiest way to seek validation is to nix no from your vocabulary.

So when it comes to borrowing money, picking her up, eating at fancy restaurants, watching her shows, or picking up her laundry, you invariably say, yes.

I’m here to tell you no.

Again, check your motivations.

If you’re saying yes not out of the goodness of your heart but because your self-esteem needs a hit of validation then perhaps it’s time to address some bad habits.

5) You Mirror Her Behavior

This one is interesting.

Mirroring someone’s behavior early on in a relationship is a sign of affection.

On first or second dates or when you first meet someone, you’ll notice mirroring taking place if there’s attraction. 

By mirroring I mean, you mimic their actions. If she touches her hair you’ll touch yours, when she reaches for her coffee you also take a sip of yours, and when she takes her coat off you take yours off as well.

If done early in a relationship this habit may not be seen as toxic.

But this dynamic takes on a new light if the habit continues into the latter stages of a relationship.

If you’re still mimicking her later on it’s as if she’s controlling you via remote.

Be your own man.

You may think this tactic will help her like you more — it won’t.

At least not in the long-term.

6) You Crave Praise

Do you go out of the way for a pat on the head?

Do you do good deeds and make an extra effort to remind her of the good thing you’ve done?

It’s easy to say you shouldn’t do this, but you’re human. We all crave praise from others, especially those we’re attracted to. You know when it’s an unhealthy behavior when you feel zero gratification unless she approves of your actions.

approval seeking behavior

7) You Say You’re Always Fine

There’s putting her first and then there’s always putting her first at the detriment of your own wellbeing.

Magically you’re okay when she offends you, borrows your car without asking, locks you out of the house, and feeds your dog grapes.

You appear super chill but inside you’re fucking dying.

You’re not okay, this sucks.

Stop repressing those feelings. It’s okay to speak up for yourself.

That’s the only way to have a healthy relationship. I know you’re repressing your feelings in an attempt to win her over, but it’s actually doing the opposite. As a result of always saying yes and you’ll slowly begin to resent her.

8) You Fudge The Truth

Do you embellish your stories?

Do you make yourself out to be the hero?

The people in your stories are always bigger, brighter, scarier, and more beautiful than in reality.

But they don’t know that.

We all embellish, but you just happen to embellish more than the average joe.

approval seeking behavior

9) Pretending To Know Everything

You wouldn’t imagine not knowing what they’re talking about.

Of course, you heard about that earthquake in Japan because you read the news, and yes of course you know the best way to approach a dog, and duh you know why we’re heading into a recession.

You don’t.

It’s okay.

You’re not Google.

It’s okay to not know and even admit not knowing everything. But you can’t imagine yourself ever asking what that word meant or if they could explain that concept again.

You just nod like an all-knowing snob and go about your day.

10) Not Handling Rejection Or Criticism

The opposite of approval would be rejection or criticism.

Does it just rip you up inside when you’re dished the slightest critique? Most people would brush it off but you take it like a poisoned blade to the heart.

No one likes rejection but this is your kryptonite.

Luckily there is a way to not be so dependent on the opinions of others.

Here are a few ways to address those approval seeking behaviors.

How To Stop Approval Seeking Behavior

Speak To Yourself As You Would A Child

You seek the validation of others because you don’t respect yourself. Look I don’t know you, but if you had enough self-esteem you wouldn’t go digging for self-esteem boosters.

One concrete way to address this is to start treating yourself better.

Do you find yourself self-criticizing and talking junk about yourself?

Stop throwing shade.

Talk to yourself as you would a child. Would you say the same things you say to yourself to a child or nephew?

The change starts and ends with you. The battle will be fought internally.

Start by using kinder words to talk to yourself.

Have A Solid Social Support System

The craving for validation may have arisen from a lack of validation early on in your life.

Perhaps your parents or friends weren’t supportive as a child. As a result, you’re always looking for others’ opinions of yourself to boost self-esteem.

Surround yourself with positive people. Find friends that will build you up instead of break you down.

Write Down Daily Accomplishments

Make your awesomeness unavoidable by writing down daily accomplishments. It doesn’t matter how small they are. The point is that you’re cooler, smarter, better looking than you think.

This list will help you realize that.

Meet More Supportive Women

Is the woman you’ve been dating damaging your self-esteem?

Maybe it’s time to meet more women.

But how do you do this?

In my coaching program, Dating Decoded we teach men how to leverage IRL social groups and online dating to find compatible women.

We’ll give you the skills you need to go on a host of dates with all kinds of women. Instead of settling for someone that brings you down you can quickly find a woman that values you.

To learn more about our program I encourage you to book a 1-on-1 Zoom call. During this chat myself or a coach will learn more about your dating background and show you how our program can give you the skills you need to find compatible women.