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20 Rules of Dating You Must Follow and 20 You Mustn’t

20 Rules of Dating You Must Follow and 20 You Mustn’t

Updated on Nov 08, 2022

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

20 Rules of Dating You Must Follow and 20 You Mustn’t

Let’s accept it: some of us function better with rules. Be it dieting or dating! Yes, there are certain rules to dating, as well. After all, no matter how much experience you have had, a date with a new someone is intimidating!

You are confident, comfortable, good at making conversations, but the moment you’re required to establish a comfort zone with a stranger, you get confused.

What to do, what not to do… Even if it’s a casual fling, you don’t want to make a fool of yourself. And especially if you are planning a long-term relationship, the rules of dating are a must-know for you.

However, you don’t want to follow all the rules that flood social media. With time some of the rules get outdated, and they ruin your impression more than creating one.

Don’t worry this time you’re in safe hands, because here you’ll get both: rules that you must follow and rules that you mustn’t.

First up, let’s see the rules that you should follow on a date.

Rules of Dating Infographic

20 Rules of Dating You Must Follow and 20 You Mustn’t
20 Rules of Dating You Must Follow and 20 You Mustn’t

20 Rules of Dating Everyone Should Follow

With the world evolving faster, we definitely need to give dating a spin. And guess what, we have… with this list of rules.

I know dating and relationships are not easy to master. But the good news is, these basic dating rules are not gender-biased! In fact, today we’re going to smash whatever little favoritism existed in the past dating rules.

Following these rules will make sure you have a memorable dating experience…. And also leave your partner wanting for more… 😉

Hurry up…. Let’s start!

1. Date only when you’re willing to date

Whatever the reason maybe, if you are not prepared to date someone, then just don’t. Maybe you don’t like the person, or you are not prepared to let someone in your life.

All the reasons are justified, and it is always better to stick to your comfort zone, when it’s about dating.

If you commit to a person who you don’t see worthy, you are going to make them feel inferior, sooner or later. You will spread a negative aura, and both of you are going to dislike it.

No matter the reason, if you’re not ready to put yourself out there, then just don’t! Because it’s only gonna bring in more drama.

2. Keep the dates short and beautiful

Fixing a certain time period for the date will ultimately save your heart from walking into the wrong direction.

Extending the date longer than planned will mislead your heart to make imbalanced choices.

Do you remember what happens when you spend a lot of time at a shopping center: you start liking everything, and then all of a sudden you like nothing. At the end of the day, you return confused and disappointed.

Similarly, if you spend hours on your first date, you are most likely to be confused with the mixed signals your brain gives you.

It is obvious that you want to spend more time knowing this person. But think about it like this: But can you decide your fate based on one date? No, right?

Then why invest more and more time on the very first day? Give yourself and that person more dates, and not “a longer date”.

3. Know what you want in a relationship

Not everyone is looking for lifelong attachment. But if you are, you need to be straightforward and honest about it.

While you expect a long-term relationship, the other person might have no such plans.

And it’s totally your fault, honey. You did not communicate about your wants when you had the time.

If you think revealing your plans will scare them away, then you cannot be more wrong. If they are the right person, they will give this budding relationship a chance, nonetheless.

If they aren’t, then don’t waste your time. They don’t deserve your love, it’s you who is hanging onto a thin branch!

4. Don’t be judgmental

It’s not important to give your judgment on each and everything you come across. It just portrays you as a judgemental human being, and trust me, that’s not a lovable characteristic.

For example, you might think that this person favors stereotypical behavior and that somehow makes you lose interest. But take a moment and understand where they’re coming from. Don’t judge.

Understanding the person’s views, their preferences gives you more validation about whether or not you want them in your life. So, why judge?

5. Be a good listener

This is one of the most important tips on this list. Always remember that you will be tempted to speak a lot on your date.

You are simply going to love boasting about your achievements, talking about your interests, and narrating adventurous stories of your life.

But when you start talking a lot about yourself, you overlook your dating partner. They too have a story to share, but you’ll be a party to it only when you give them a chance to speak!

So be a good listener while on your date. Don’t cut them short when they seem to be sharing something significant.

6. Don’t feel forced to send a thank-you text

Once you’ve already shown gratitude, there’s no point in sending a text afterward.

I have seen men and women sending long thank you notes and listing one by one – all the things that were the highlight of their day.

I can understand if you are doing this on a call when both of you are already in a relationship. You are recalling your first date and talking about it casually. That’s fine and acceptable!

But, doing all this on a text message when you have just returned from the first date makes you look “too-much” – if you know what I mean.

Instead, ask them if they reached home safely, or anything else… but not a thank you, please!

8. Sex shouldn’t be your priority

Sex shouldn’t be on your mind on your first date unless you both want the same thing. Love-making is different than sex – It takes time and effort to create a bond where you can feel safe with the person.

The comfort that you built with time naturally takes you ahead and you both get intimate. This is a very natural process; it shouldn’t be forced.

If your dating partner is not very comfortable with having sex on the very first date, please don’t try to convince him/her.

When you cannot even determine whether you actually see this person to be your better half, how can you even think of making love to them?

Further, it just portrays you as a lusty person, and nothing more.

9. Eat whatever you want.

You’re a big-time foodie, but you still hesitate from ordering your favorite dish in the fear of being judged? Seriously?

Why would anybody not want someone who loves food and enjoys every bit of it. I know people are shy at expressing what they want to eat…. because the “first date” rules told you not to.

But hey, here’s me busting this myth for you: Eat whatever you want.

If someone doesn’t appreciate you being a foodie, then how do you think they’ll be able to accept the other parts of you?

I’m sure you don’t want to keep hiding your real self all your life. So, never pretend, not even on the first date, let people love you the way you are.

But make sure you don’t order in excess and waste. Because this may mean that you do not value food or the efforts made to put that food on your plate.

10. Be accepting, not demanding

Everybody might not share the same interests as yours…. And that’s absolutely human.

If you select a friend or a partner on the basis of matching traits, or matching interests then let me tell you: Common interests do not define your compatibility.

Your compatibility depends on your acceptance. Expecting your partner to be the exact same version of you shows that you are demanding, not accepting.

You, yourself, reduce your chances of finding a compatible partner.

So don’t let contrasting opinions and perspectives bother you. Remember, as long as both of you are individually doing good, and you accept each other, you will make a power couple.

Be an open-minded person with no expectations and gradually, who knows you both will change each other for the better.

11. Stay alert

Never, I repeat, NEVER be tolerant of discomfort on your first date. You never know what a person’s real intentions are. But you definitely know that your safety is in your hands.

On the flip side, you must also make sure that your company feels comfortable and safe. Always choose a public place for dating and keep your hands to yourself.

And if you’re dating this person who gives off a creepy vibe, touches you without permission or is sitting excessively close to you: Be Vocal about it!

Whether you are a man or a woman, if you see that things are offending you or you’re not feeling safe, leave the place immediately.

12. Spread positivity

Radiate the positivity that everyone yearns for.  

Never let negativity enter your dimensions. It won’t fix things, rather it will make you lose your confidence and you will ultimately end up messing things up.

Be positive even while planning the date. Think about the good things you can do to make it more memorable. Don’t overthink. Learn to go with the flow.

With the world becoming so complex and survival getting harder, we definitely need people who are sorted and optimistic. So, why not?

13. Be friends first 

Every relationship starts with friendship. Good friends prove to be the most compatible and loving couple. Don’t pressurize them with the baggage of a relationship on the very first meeting.

Let them be comfortable with you, so that they can laugh their heart out and share their life with you. Even if this does not end in a relationship, you will definitely earn a new friend.

Remember, friendship is based on a no-judgment policy. It’s the best way of truly knowing a person. Even if you enter into a relationship with this person, you would know what you’re getting yourself into.

14. Don’t force anything! Comfort zone is important


It’s a normal human instinct to expect.

But what you expect may not always be right and vice versa.

When two strangers meet, they need some time to build a comfort zone… and this “time” can be of different duration for different people.

So, you take your time and let your partner take their time. Do whatever makes you feel comfortable.

Neither force yourself, nor expect your dating partner to do anything out of their comfort zone. If they are not comfortable trying vodka, don’t try to convince them.

If they force you to do something which you are not comfortable with, then just know it doesn’t matter how hard you try to satisfy them, this relationship is never going to run smoothly.

15. Communicate smartly

Your communication skills can help distinguish a good date from a bad date.

If they sent you one text but you replied in ten text messages, honey be sure they’re never going to look back.

One text has to be replied to in one text message, alright? Otherwise, you just end up portraying yourself as a clingy creep, who has no other commitments.

If you missed a call from them, don’t call back a dozen times. Make ONE call back, if they pick up fine. If they don’t, let them come back to you.

Be responsive, but don’t be too prompt or they may sense the desperation lingering in you.

16. Have a good sense of humor

Who doesn’t want to be with a person who can make them laugh even in weird and awkward situations of life?

Just like spreading positivity is an art, spreading smiles is an art too. And laughter is contagious.

So, make sure you don’t keep your date serious and boring. Some comic relief works like oxygen here. In the end, if nothing works, at least both of you will part ways with a good laugh… and pleasant memories.

17. Don’t reveal too much, too soon

Never be an open book. Not on the first date. Be a mystery and let the other person indulge themselves into reading every page of your life. Don’t initiate a conversation that includes your past.

It’s your first date, make it more fun and not only about sob stories. Even if you do, never give an explanation for everything that happened. Only convey the actual facts.

Observe how the other person is unveiling itself, this will give you a sneak-peek into their mind and heart.

Be picky about the information you deliver. Not everyone out there is trustworthy or deserves to know everything.

18. Don’t forget your ambition  

Bitter and a true fact: You will not be known for the number of people you have dated, but you will definitely be known for your professional achievements.

Dating shouldn’t be your topmost priority, following your ambition should be. Your partner shouldn’t be your life goal, instead, they must help you achieve your goals in life.

Learn to love yourself and work on what you aspire to become.

So, choose someone who motivates and supports your life goals. Work on building yourself to be a strong personality.

19. Don’t rush into a decision

A couple of dates didn’t work and the partner didn’t turn out as expected… Now you have shut the door completely because maybe, “dating is not for me!”

Or let’s say, you meet a person who is NOT TOXIC, but did not impress you much. Now, you are not ready to give them another chance or you rejected them too fast.

It’s easy to find someone for casual flings. But real gems for long-term relationships are hidden and you need to have the eyes to spot them.

Also, it requires time and effort to create a bond that you can back on. So, be patient and do not give up easily. Remember, that good things take time.

If you hurry into such decisions, it won’t be a surprise if it turns out to be a lifelong regret. Would you want that? No! So, hold your horses, buddy!

20. You can always explore

The world is huge and you have ample opportunities to explore. You have to walk on different paths, and then decide which path actually leads you to the desired destination.

Similarly, if you find a dating partner to be toxic, you can always choose to leave the date and the dating partner.

But that shouldn’t stop you from exploring. Talk to more people, go on multiple dates and then commit to a person you’re absolutely sure about.

Different people give you different vibes. Not everyone you meet can be your soulmate… but there’ll surely be someone who tingles your heart in a way others didn’t. Plan a second date with them and see where it takes you.

These were the DO(s). But we also have some DON’T(S) too. So, let’s dig in to read that.

20 Rules of Dating you must stop following today

Firstly, let me tell you these rules are not to stop you from being who you are.

At the end of the day these forbidden rules are nothing but the unnecessary stuff that you should not carry to your first date, if you’re yearning for a pleasant experience.

The 90s old school dating rules don’t work anymore. So, let’s step into the modern dating world where everything is fast and real… with a list of 20 rules that you must STOP following, immediately.  

1. Let the man initiate first

Alright, I don’t know who said this… but this is the height of patriarchy.

Why would you expect a man to initiate everything? The world has progressed so much and so should you.

Infact, there are men who take offense when you expect them to comply with the stereotypical “men” dating rules and at the same time, there are fearless women ready to take on all the challenges and initiatives.

I mean tell me one logical reason that they shouldn’t be taking the initiative…. why? I’m sure you didn’t have an answer. Don’t you think it’s time to dump this rule, right away?

2. The bill is on the man!


When two people go on a date, and both of them earn their own bread, I don’t see a practical reason why a man must pay the entire bill.

Sure, it feels really nice when you have someone to pay your bills but hey, this cannot be a rule, right? This rule is as ancient as time, and simply not needed at present.

3. The man should pick-up her lady love

Yes, you may recall some Vintage movies where the lady love would smile from the balcony, while the man would be waiting on the front door, in his car, to pick up the lady from her house.

But in today’s gen when you both are independent and empowered, there’s no reason why either of you must pick each other.

Both of you can decide upon a mutual spot and mutual time to meet. Keep a buffer of 10-15 minutes, but not more than that.

4. The 3-days gap

“Wait three days before contacting your date.” What are you even talking about, buddy… that’s absolutely ancient now.

Honestly, I find this to be another superstitious advice that needs to be dumped right now and here.

In fact, it is quite the opposite in the present day. If you don’t contact the person who you have dated for the next three days, the person is just going to feel detached, and they will assume that you are not interested in them.

As a result, they will move on with another person.

So, make contact if you wish to… there’s no right time for that!

5. Date thrice before having sex!

You must have heard about this third date rule that says: Don’t have sex until the third date.

Of course, that’s not possible. And, if both of you are comfortable and willing, why should you bother about a stupid rule?

Maybe you had a bad experience with the last girl or guy but that does not mean this becomes a rule to wait for X number of days before having sex with a partner.

6. Don’t say NO on the first meeting

Don’t believe it… trust me, there’s no time to say a NO.

If somebody makes you feel uncomfortable on the first date, you can step out immediately. You don’t have to wait for several days, disappoint yourself even more, and then say NO.

Yes, everybody deserves a second chance, but if the second chance is given to the wrong person, then they can play with your mental peace and happiness. Choice is yours.

7. Don’t kiss on the first date

The rule says: “Don’t kiss your dating partner on the first date, or else they are going to see you as a lusty husband or wife…”

Well, I feel these rules induce partial judgments in our heads. Maybe the rules are made because people, even after being so educated and modern, are so judgemental.

The rule is nothing but an implicit judgment on someone’s character, without even knowing the person. I don’t see any reason to promote this rule, so it deserves immediate dumping!

Honestly speaking, if you are open to determining your chemistry with the person, then ending the date with a kiss can be very helpful, provided the other partner is comfortable.

8. Follow what your date plans

Yes, it is so sweet of you to allow your dating partner to take the lead, and make the choices.

But this doesn’t mean that you shouldn’t have choices of your own. Plus, not taking any initiative will make you look like you are not clear about your decisions and choices in life.

If you start putting yourself on the corner right from the first day, then your relationship will always seem heavy on you.

Eventually, your partner may also take you for granted and expect you to adjust every time.

Now if you have no problem being at the backfoot in the long run, then absolutely no problem. But if you can’t. then you must make a wise decision.

Like, lay the foundation of a balanced relationship, where both of you make mutual choices.

9. Talk only about love life and romance

This rule says to avoid any serious topic of discussion on your date. Well, it may or may not work in your favor.

While a discussion on light topics can initiate fun conversations, talking about serious matters helps you in understanding each other’s opinions better.

You will see the vulnerable side of your partner that lets you evaluate your compatibility, and make an informed decision.

On the contrary, keeping all your conversation light and airy would only give you a superficial understanding about them. That won’t help, honey!

10. Men and women can’t be “just” friends

A lot of times, when you date someone, you gel well, find compatibility, and yet don’t see that romantic spark.

So, does that mean you have to choose either of the extreme options? Like you can either be girlfriend-boyfriend, or simply nothing!

Let me give you a third option here, where we will be dumping another old-fashioned rule.

Both of you can be friends!

Don’t let the pressure of extremes ruin your date or companionship. If you have found a person who is compatible and both of you vibe really well, it does not have to end up in a romantic relationship and nor do you have to break ties with them… make a fist bump and be friends!

…and help each other find a date! 😉

11. Seek approval from your date’s parents

Hey, this rule is so annoying that it can put a bar on your dating plans forever…

Why would you involve your families in something that doesn’t even have a solid direction as yet? You don’t even know if things would end up in a relationship.

Then why bother the parents unnecessarily? It’s nice if you want to take their permission, but it cannot be a compulsion… Your comfort matters!

12. Talk less

Again, the fear of judgment. The rule has been made just to save you from judgments. It’s like putting on a blindfold so that you cannot see the danger in front of you.

Remember, a good conversation on the first date can lead to a successful relationship. You should be free to talk about anything that is important to you, anything that interests you.

If you want to know about something, don’t feel scared to ask about it.

Let them judge you all they want to. At least, you will be saved from a toxic relationship.

Remember, the right person will never judge you for your concerns or emotions.

13. Dress up even if it is uncomfortable

We often hear people saying: No Pain No Gain! But for God’s sake, stop applying career rules into the dating world. This is about relationships.

Here, either you will be sharing love with a partner who deserves you, or you walk away single.

In both cases, your attire shouldn’t be a concern at all. Yes, you definitely need to look clean, tidy, polished, and well-groomed, but it shouldn’t put you in an uncomfortable and suffocating spot.

If you don’t see yourself walking comfortably in high heels, there’s no pressure sweety! Tell him about it.

If he is not supporting you here, I assure you he is not going to support you anywhere… And the same applies to the boys!

14. Let them chase you

Don’t you think this is extremely manipulative?

These are matters of the heart. Yes, your mind is just as important, but not in this manipulative way. You don’t need to be a shrewd calculator who measures every step before walking.

If you like them and you are interested in them, you shouldn’t play chase before the much-awaited YES.

But at the same time, if you don’t see a future in this relationship, why keep them hanging?

15. Don’t date anyone from your friend’s past

Look, you never know what went wrong between them that lead to breakup… nor are you going behind their back.

So, what’s the harm?

Meet this person, and if you like them, then you must absolutely go ahead. And if you don’t, the whole world is waiting for you.

And when you meet the same friend while you’re in a relationship with their ex, and they give you a scornful look… know that they’re not your true friends!

16. They have to show up with flowers or gifts

Gifting someone or making someone feel special is a wonderful idea. You give them a bouquet to make them feel like a king or queen, that is absolutely fine!

If you do this on your own, cool. But it shouldn’t be a predefined “rule”.

If they give you something, brilliant! But if they don’t, no need to get disappointed.

This is also no reason to reject someone. It doesn’t mean that they are not interested in you, maybe gifting is not their love language.

17. Treating dates like interviews

Don’t let this date turn into a Q&A night. This is not an interview where you’re interrogating someone, it’s a date where you both must enjoy all while knowing each other.

Also, don’t force yourself to impress someone. Be yourself. If they like you, fine. If they don’t, then it’s not your fault.

Coming prepared with answers feels so formal and planned. Don’t do that, be raw and real.

Just go with the flow and believe that the right person will love you for you.

18. Don’t reveal about your ex

Wait, I understand if someone is suggesting you to not dig into your partner’s past because you don’t want to hurt them.

But if someone has asked you about your ex, you can always reveal it. Why wouldn’t you? 

Maybe, they just want to be sure that you’re over your past so that the present and future go unaffected and smooth.

So, tell them whatever happened, talk about the bitter experiences, if you had any. All of this is going to give them a clear picture of your life, so no harm in doing it.

19. Flatter them

There’s no harm in complimenting your date if they look good… but only if it is right from the heart.

But this doesn’t mean that you start bombing them with compliments. Two or three genuine compliments are sufficient. Anything more than that sounds like false flattering, which is not appreciated by any.

Plus, you sound SO creepy.

 20. Don’t talk about marriage on the first few dates

Absolutely, stupid!

If you are interested in someone, and you see a beautiful future with them, then why should you wait for the big day. If both of you are ready for the commitment, then just go for it.

I agree that the decision is sensitive, and it requires proper time and mindful preparation, but having said that, it depends from person to person.

If you see you have got a compatible partner, there is no need to delay the process.

A word from ThePleasantRelationship

I am sure most of your queries about how to date someone have been answered here. These rules cover all aspects of successful dating.

But remember, dating is not your whole life, it’s just a part of your life. It definitely needs some commitment, but not so much that you lose your individual self.

These do’s and don’ts cannot change you or your personality, but they can definitely help you put your best foot forward, when you are with someone special.

And what the rules cannot teach you, experience definitely will!

So, the bottom line remains the same, start dating… you’ll learn everything else in the process! 😉

Are you interested to know more about ‘Millennial Dating’ then click here?