Are you horrible at saying no because you want to please everyone? Do you throw all your dating etiquette out the window because you usually say “yes” even when you want to say “no?” 

I know how you feel. I’ll be honest with you, I’m a people pleaser. I don’t like to make anyone unhappy with me. Maybe it’s just an incredible faith in human nature that is unfounded, but sometimes I believe that if things are stable, they’ll just stay that way. 

This kind of thinking gets me into trouble. Why? Because in order for others to be happy, that sometimes conflicts with what I need to be happy. 

For instance, if I know that my partner doesn’t like something sexual that I like, I push it down and don’t bring it up again. But this is what got me into trouble last year when my dissatisfaction ended in the breakup of my nearly 8-year relationship. Luckily, we’ve decided to get back together, but I’m recognizing that something needs to change on my end. 

You see, if we don’t speak up about what we want, need, like, and dislike, then no one on the planet will ever be able to satisfy us.

When it comes to dating etiquette for men, many guys don’t realize how their inability to say no can stop them from developing the right connection with women. Bottom line, people-pleasing and dating don’t mix. Here’s why — and what you can do about it.

Dating Etiquette for Men Who Are People Pleasers

What Happens When You Can’t Say “No” in Dating 

“I’m not very good at setting boundaries and limits.”

This is something I hear my clients say a lot, and it goes hand-in-hand with learning how to say “no” and to ask for what you want. Without boundaries, we can get pulled into everyone else’s drama. When that happens, we lose our sense of self. Who am I without boundaries? Not myself, certainly. 

Instead, holding your frame and maintaining your boundaries is sexy to women. When you suggest boba tea for a first date, and the woman you’re talking to says, “Let’s get dinner instead,” do you cave or do you hold your frame? 

Are you able to say, “Sorry, I only do dinner on third dates, you’ll have to earn that“? 

It’s important to understand that saying “yes” to whatever a woman says she wants won’t always please her deep down. That’s because women, myself included, like to subconsciously run tests on men. She may be suggesting dinner not because she really prefers dinner, but because she wants to see how confident you are. Will you immediately go along with what she wants? 

If so, she knows she’ll probably have to keep running things in the future. This makes her feel less safe with you since you don’t seem to take charge. Don’t take it personally, though. We’re programmed because of evolution to subconsciously look for the “alpha” guy who can protect us. Usually, we don’t even know we’re doing it. 

So, just remember: When you suggest coffee and she counters with dinner, caving in because you have no boundaries only hurts you. You may feel as though you’re being nice by pleasing her, but in reality, you’re setting yourself up for failure and becoming a doormat in the process.

Once You Become a Doormat, Watch Out

If you keep deferring to the woman you are dating, you’ll end up with a problem on your hands. This problem often manifests in the feeling that “I haven’t gotten a lot out of my relationships emotionally” or “I often feel like my partner and I are emotionally distant.” 

I hear this a lot from my clients as well, and I’ve also felt this way myself. You can even gradually begin to resent the other person for always “making” you do what they want — but this is an illusion. 

I’ll use my own relationship as an example. Many times, I’ve felt as though Tom didn’t understand me. Yet, that was because I wasn’t telling him what I wanted and needed. I was saying “yes” to everything he wanted, even when it meant sacrificing the things that I wanted. 

This inability to say “no” turned me into a puppet, just going along with whatever strings my “puppet master” wanted to pull. And the thing is, I was resentful of him. I was thinking that he’d made me that way. But in reality, my silence put me there. My silence made me a puppet. I forgot myself. I should have said “no” to golf and “no” to Superbowl games with teams I didn’t care about. And I should have spoken up and asked more for what I wanted. 

Resentment is a relationship killer. While I thought I was being “good” by not saying “no,” what I was really doing was chipping away at the foundation of my entire relationship.

The Biggest Reason Why Saying “No” Must Be Part of Your Dating Etiquette 

You have to be able to say “no” in dating if you want to demonstrate your value to women. Women love men who know who they are, where they’re going, and who don’t apologize for what they want. 

But this isn’t the biggest reason why saying “no” must be part of your dating etiquette. The biggest reason is this:

If you can’t say “no” to the wrong woman, you won’t be able to open yourself up to the right one.

Whenever I think of this principle, I’m reminded of a quote from Steve Jobs: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully.“

That’s exactly how you have to be in dating if you eventually want to find the right woman (and have her treat you well). You need to stay focused by not saying “yes” to a bunch of things you don’t want.

It’s kind of funny how some of the best dating advice comes from billionaires, actually. I love Warren Buffett’s three-step process for achieving your goals — and you can do it, too. 

1. First, write down your top 25 life goals. 

2. Next, circle the 5 that are MOST important to you. 

3. Then, eliminate the other 20 and focus only on your top 5 until they’re done.

Yep. Just cross those other 20 right off. The reason why, he says, is that your time is limited. “You’ve gotta keep control of your time, and you can’t unless you say no. You can’t let people set your agenda in life.”

A-freakin’-MEN.

If a woman wants something from you and you’re not feeling it, you must say no. Otherwise, you not only set yourself up for misery, but you let yourself get sidetracked into accepting less than what you want. Then, by the time the right woman comes along, you won’t be available.

Exercise: Objection Handling By Saying No

Here’s an exercise that might help you say “no” more easily as part of your dating etiquette. When women try to push their preferences on you during dates, hold your ground instead of giving in.

Some examples:

She keeps inviting you on dates but your schedule is too hectic (and you’re not that interested): 

“Thanks for thinking of me, but I have too much on my plate right now.” Or, “I’m sorry, this just isn’t working out. I like you more as a friend and I wish you the best of luck.”

She’s hungry and suggests you get dinner on a first date (while you’re at happy hour):

“I would love to go with you but unfortunately, I can’t because _______ (I’m allergic to wheat / I never do dinner on a first date / I only do dinner on a third date / my trainer will kill me / I only do dinner with family and loved ones, etc.).”

She says she prefers wine over coffee:

“I don’t do wine until date #3. You’ll have to earn it with coffee first,” or “Well let’s do coffee first so I can see if you’re an ax-murderer,” or “Right now I don’t really have a taste for wine. We can meet for coffee another day.”

Says she can’t meet Saturday, but how about Sunday?:

“Can’t do Sunday, that’s family lunch day” or “Can’t do Sunday, how about Tuesday?” or “I’m on call Sunday, how about Tuesday?”

She lives far away and wants you to come to meet her, rather than her coming to you:

“I’m on call and can’t leave Portland.” Or, create such a compelling, once-in-a-lifetime TDL that she WANTS to come to you.

She wants to order a bottle of wine rather than getting an individual drink:

“I don’t drink wine but actually they have this amazing drink ________ (insert description of a unique drink worth trying).

She wants to stay for one more drink:

“I can’t, I work early in the morning,” or “I have to drive. One’s my limit.”

She wants to grab an appetizer:

“I just ate,” or “I really shouldn’t, I’m on a special diet,” or “The appetizers kinda suck.” Or just simply, “I’m good.”

She wants to split the bill: 

“Nope, my momma would slap me upside my head,” or, “No way, that’s horrible dating etiquette!”

She wants to talk more on the app before meeting up for a date:

“Why don’t we chat on FaceTime so I can make sure you’re not a catfish/ax murderer? 😉 I’ll be free around 8 p.m. tonight if you want to call me at xxx-xxx-xxxx.” Or just, “Works for me but my thumbs are broken, let’s chat on FaceTime…”

She wants to keep dating but you don’t:

“I know this isn’t the answer you’re looking for, but…”

All she wants to do is text and you want to talk on the phone:

Either stop responding or say something like, “It’s an honor to be your penpal but I’ve reached my iMessage limit. ;)” or, “My thumbs are getting tired. I’m a lot better with my lips.” Or, you could also just call her if she’s sending positive messages.

She’s busy studying and can’t go on a trip with you:

If you were a better manager of time, you’d figure this one out! Pitch the trip better. (See my post, How to Ask a Girl on a Date and Get a Hell Yes.)

49 Ways to Say “No” to Anyone

I absolutely love this list of ideas called 49 Ways To Say No To Anyone (When You Don’t Want To Be A Jerk). Steal some of these, and be sure to check out the full list.

1. Use the word.

2. Or a firm (but polite) alternative.

3. Don’t Costanza it.

4. Avoid going on and on.

5. Don’t be afraid to say it twice.

6. If need be, use “because.”

7. Just smile and shake your head.

8. Be assertive.

9. Don’t take freebies.

10. Ask yourself: If all your friends were jumping off a cliff, would you?

11. Remind yourself of the opportunity cost.

12. Read up on the tricks used by con artists.

13. Trust your gut.

14. Provide an alternative.

15. Pass that buck.

16. Negotiate.

17. Don’t delay.

18. Go ahead and change your mind.

19. Say it often.

20. Add, “What a shame.”

21. Get over the disease to please.

22. Crystal-ball it by figuring out when you’ll have to say no.

23. Avoid serial askers.

24. Remember, a white lie never hurt anyone.

25. Say, “Not now.”

Dating Etiquette Is Easy Once You Learn to Stop People Pleasing

Warren Buffett once said, “The difference between successful people and really successful people is that really successful people say no to almost everything.” He was so right.

If you want to succeed in dating, you actually have to say “no” more than you say yes. This isn’t easy for everyone, but hopefully by now, you get how important it is.

The good news is, I’m a coach who’s been there when it comes to people-pleasing. Once you book a session with me and we get to know each other, I can not only help get your dating etiquette back on the right track, but I can also work with you on saying no.

Just by doing that, you’ll be one huge step closer to becoming the type of guy that women literally crave. So, what are you waiting for?