5 Dating “Rules” You Should Break

Since when did the dating process become a science experiment? There are no set constants or variables that can predict an outcome. If you change X, you do not automatically get Y.

We are complex, emotional creatures who all react positively and negatively to different circumstances, and the only way to learn what each other is like, is to dive in.

Here are 5 ‘rules’ that should go out the window next time you’re courting someone new.


Waiting 3 days to call.

This one is typically for the guys, but who made this up? I know, it’s supposed to be so you don’t come across too eager or willing. Well, what if the girl whose number you got is waiting for you to call because she’s eager too? Doesn’t everyone want someone to want them?

If you wait too long, she might think you’re not interested and ignore your call or text. Now look what you’ve done.

Only men can approach women, not the other way around.

As a guy who frequently endorses chivalry, I insist on taking the lead when it comes to dating, typically. However, everyone likes to feel wanted and desired. The only reason why I’m with my girlfriend is because she recognized me from a party we were both at in the past and approached me at a lounge in Boston. If she hadn’t taken the initiative, odds are we never would have reconnected.

I then, of course, suggested we get together and planned the dates from then on out – but the initial approach came from her.

Girls, I know how unnerving it can be to approach someone. Fear of rejection sucks, but do you know what sucks even worse? Missing out on someone great.

Guys, even if she approaches you, you still pay.


Waiting for him to text you.

So, you went out and had a great night together and talked about setting a second date. Now, a day or two goes by and you haven’t heard from him – you probably start running through all of the things that could’ve gone wrong in your head. While I maintain that a guy should call/text a girl after their date(s), not everyone might agree with me.

Instead of waiting around, take the initiative and reach out. Sending a fun, casual text letting him know what a great time you had won’t be the end of your relationship. And if it is, he wasn’t the right guy anyway.

No sex on the first date.

Controversial opinion, you say? Well, I’ve got one of those.

I don’t believe in waiting a certain amount of time to go all the way in order to solidify the relationship or whatever the goal is. I think if two people share a mutual connection and are two consenting adults willing to act on it, they should act on it.

Waiting too long and having a bad intimate experience is worse than having a great intimate experience early on. If you make this decision and a man doesn’t call you afterwards, it is not because of the decision you made. It’s simply because he didn’t feel the same connection you did, and probably wouldn’t have called anyway.

If you two have a great time together and enjoy each others’ company, it’s only natural to want to continue that moving forward.

Now, if you sleep with every person on every first date then you may need to re-evaluate your methods. But if there is a real connection early on, I say go for it.


Assumed monogamy.

So you’ve gone out a few times now and you start to tell all of your friends that you’re “dating.” Not so fast…with the prominence of social media and a culture less willing to commit, this is a discussion that needs to be had.

After a few dates when a connection starts to form (or even earlier), you may be less willing to spend time with other people, but before you put all of your eggs in one basket, make sure that they feel the same way.

Don’t bring this up too early or you might scare him/her off, but if you have consistent plans together and are spending a lot of time with each other, it’s a good time to make sure you’re on the same page.


For better or worse, the dating world has changed. It has become easier for some, and more difficult for others. Typically issues arise when both parties are playing by a different set of unspoken “rules.” How can you win a game that you don’t know the rules to?

For this reason, I’ve always felt it’s better to leave the games out of the process and just be up front and honest with the other person.

If they are right for you, they will understand and reciprocate. If not, you will find out early on. Either way – you win.

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8 thoughts on “5 Dating “Rules” You Should Break

  1. I was really enjoying your blog up until the “sex” part. What part of having sex while dating is being chivalrous or gentlemanly? Sex is meant for procreation, so if the man is really a gentlemen, he will say “I do” at the altar before the act. A true gentlemen also practices chastity, the two go hand and hand and it is really hard (almost impossible) to have it either/or.

    1. I respectfully, but wholeheartedly, disagree with your point here. The two can absolutely co-exist and there is no reasonable or logical explanation to the contrary.

      Thanks for reading!

      – JMS

  2. I enjoyed reading the article but i was bothered about the “No sex on the first date.” thing. Well some of the girls of today’s generation would prefer/agree to have sex on the first date but as for me I would rather get to know the guy deeper before getting into that part and only when we get married. And as a real man, you have to respect the girl until you become one in marriage.

  3. I enjoyed this article a lot and I agree some dating rules should be thrown out the window. You mentioned not bringing up monogamy too early but what if you have talking to a guy for roughly 2 months and you have a great connection with him but a) he goes to a different university and b) you have only hung out with him for one weekend? What do you do especially if it seems like he’s really into you?

  4. I think dates should be just like any other first date. In some ways, your advice can worsen some dates, because you both have certain expectations of one another. One should stay cool and treat it the same way, as any other first date. Your partner will find out if you are really the person that they expected you to be. One should relax and enjoy themselves, it could be the beginning of something big! The little white lies are easy to say, but clear the air sooner, rather than later or they will come back to haunt you. Be careful with what you say but remember to have fun too.

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