Fuck The Rules of Dating

In hindsight, I’m aware of how needy my initial entrance into the dating scene post divorce was. Fresh off the heels of a 14-year relationship, I felt like I was genuinely ready to start dating. I thought meeting new people would be an important role in moving forward, but I also realize I had adopted a sense of normalcy in waking up each morning to “the love of my life” and a sort of desperation to return to that known normal.

I had turned 30 years old just days prior to my divorce becoming official so 50% of my life consisted of being in a committed relationship with my high school sweetheart. Having that one person by my side was all that I knew. The lifestyle of dating seemed exciting to me, but I was giving off these mixed signals of being totally cool with something casual and yet also entirely desperate for that daily “good morning” text that would bring me back to the normality of a long term relationship.

I was suffocating really great girls away without comprehending that my comfort zone of married life was causing me to pressure women into rushing commitment.

Time, of course, played a role in healing those wounds as my new normal became the single life and I embraced that freedom, but dating didn’t suddenly become easier upon finding happiness within myself. So, I also spent a lot of time proactively trying to figure out where I was going wrong in my dating efforts and I came across a variety of articles about relationship timelines.

I quickly found myself absorbing all these rules to dating.

Rules on:

what to say the first time you message someone.

how many minutes to wait until you respond.

whether you should call or text.

how long to wait to have sex.

the number of months between meeting friends and family.

when to discuss your ex.

how to avoid the friendzone.

whether to split the bill.

if you should grab a drink or go with dinner and a movie.

what to write in a Tinder bio.

when to discuss finances.

when to fart in front of each other.

when it is normal to do Netflix without “chill”.

sticking to a chronological order of major relationship milestones.

when to starting dating after divorce.

But what if it is all just bullshit?!

What if the more we absorb all this information on what we should and shouldn’t do, what we should and shouldn’t be, what we should and shouldn’t say, the more we distract from the absolute things we should do, be, and say: whatever it is our authentic selves would.

The more I read, the more I found myself constantly trying to figure out how I could encourage a girl to like me using my toolbox of dating tricks designed to create attraction. And it was frustrating when those tools didn’t work as expected. The rejection was just that much harder to accept because I had all of these dating tips and tricks that were supposed to work.

I became focused on how I must not be using the dating tools at my disposal correctly rather than maybe – just maybe – I hadn’t yet met the girl I didn’t have to make like me.

I would eventually learn facing rejection is a lot easier when you come to terms with the reality that no amount of orchestration is going to cause women to fall for you.

Instead, I just kept reading articles from “dating experts” as though winning over a girl’s heart was a game I could win by playing cards just right. Imagine the frustration I felt after I had followed all the rules to a tee only for a girl’s interest to fizzle out amidst my high hopes. I’m sure this caused me to misappropriate insecurities to unrelated aspects of my dating life because I was judging reactions I would receive against the response rate someone else had achieved.

That mindset is why I found myself reading into things, researching what a girl’s comment might have meant instead of just asking her, and worrying about whether I overstepped a boundary. I’d try to appease my anxiety by Google searching similar situations others had experienced and obsessed over whether I didn’t get a second date because I took the advice of an article that said go in for the kiss when another encouraged me to take it slower.

I’d communicate with two separate girls using the same “rules of texting” and yet still find myself anxious over whether I had texted one girl too often and the other one too little.

As one of my favorite blog posts by Mark Manson quotes:

Much of [dating] gets exceedingly analytical, to the point where some men and women actually spend more time analyzing behaviors than actually, you know, behaving.

Fuck Yes Or No – Mark Manson

And yet that’s exactly what dating continually becomes more of.

That might seem like a hypocritical stance to take from a site where you can find tips on how to improve your Tinder matches; however, I’m writing this as an important reminder that there is no magical key to dating success.

Approach Dating Advice As Perspective

Are we looking for ideas that challenge the status quo of dating with fresh perspectives to consider? Because introspection is healthy and can be beneficial.

Or are we just looking at dating advice as copy and paste pick up lines and psychological dating tricks?


If you’re looking for dating advice, you’ll find no shortage of it packaged in the vein of “10 secrets that will make any girl fall in love with you“. It gets wrapped up in cherry-picked examples that seem to guarantee results. Then marketers slap it with a $97 price tag for some desperate schmuck to part with his money under the guise that success is just a head held high approach away from another great testimonial.

It’s bullshit.

Yes, we are all works in progress that can benefit from positive change and a third party’s encouraging kick in the ass.

And yes, I know when I confronted the toxicity of my needy behaviors and comfort zones that held me back, I was able to find solutions to my very real flaws. I’m confident that those changes played a beneficial role in my life and that may resonate with people that find themselves in a loop of continual rejection.

That said, challenging someone to try new things or confront their demons is very different than telling someone that finding love is as simple as saying certain phrases at certain times, manipulating certain feelings in the other person, and elevating our perceived value through dating “tactics”.

There’s an entire dating rule about waiting 3 times as long to respond versus the person you’re texting. People will see we’re online and people will see we’ve read their message and yet we will stick to the rule because we’ve created a dating culture where our basis for building attraction are mind games that skew a person’s perception of their priority in our lives.

That’s really fucked up when you think about it.

Purposely injecting anxiety about our interest in a girl by “mystifying” her through how little of a priority she is compared to whatever else we could be doing just seems like a really shitty way to build trust.

If we resort to using dating tactics, who is the person we’re dating really getting to know?

Genuinely improving our confidence and physique is hard, though. So, you end up with the dating advice that promises fast and easy – just do this, just say that, pull these strings and wait a solid 25 minutes before you respond to that text and you’ll get the results you’re looking for.

Except, there is no fast and easy approach to dating…unless, of course, you were born with charming good looks as the heir to the throne.

There is no secret algorithm to getting laid, no secret equation for getting your ex back, and no guarantee that if you do everything oh so perfectly you’ll make that girl fall in love with you.

Dating Rules Conflict Anyways

Should you bring flowers to a first date?

Some articles suggest yes if you keep it simple and some suggest you shouldn’t at all. Unfortunately, that means any girl you take out on a first date could find the act just as endearing as another might find it off-putting.

And therein lies the problem with the rules of dating that so many people give so much weight to.

There are no perfect rules. Putting rules on how we show our love and timelines on how that love forms takes a very personal concept and attempts to turn it into a blanket equation that works for every new relationship.

It doesn’t work that way.

Our personality is uniquely ours and the person we are attempting to date has a personality that is uniquely theirs. Trying to conform our personalities to match some dating algorithm is just manipulation.

That doesn’t sound like a very good foundation for a relationship, but that’s exactly what people are doing when they react in the dating scene based entirely upon a list of dating strategies designed to make someone respond a certain way.

One girl might want to hear from you daily to know you give a damn about her and another might be turned off by that as obsessiveness.

How do you know what dating rules to follow for each one? How do you know which bloggers carry beneficial advice?

You don’t.

Stop obsessing over how some dating coach thinks an online dating profile should look, how long some random Reddit user suggests before it won’t be weird to send roses, what topics of discussion some blogger said should be avoided on a first date, and ideally how long to wait until making the relationship official or…*whew*… saying the “L” word.

Dating Advice Isn’t Absolutely Bad

There’s nothing wrong with finding perspective. There are things we can learn about ourselves and about others, concepts in social norms we might be oblivious to, and helpful tips on interpreting body language that can be beneficial. Dating advice, in general, can have value, but ultimately we must decide to be ourselves and not some manipulative version some self-professed relationship expert thinks we should be.

Taking a look at “healthy relationship timelines” was helpful in opening my eyes that the expectations I was setting for getting from point A to point B in a relationship weren’t realistic for everyone and supported me to confront my neediness post-divorce. However, there were also times I found myself sold on this idea that I was acting too nice, needed to come off less interested, less intense, and less generous to avoid being perceived as needy. That prompted me to communicate as though I was following a dating playbook rather than just let my personality lead me.

I was literally restricting myself from displaying really great and genuine qualities that some girls would fall in love with over because of the fear that girls might view them as red flags of love-bombing.

I started to think about how often the person I was dating was holding back also, scared to share their feelings for fear of coming off too intensely themselves. What a shitty dating culture we have when missed connections come from the desire to generate interest out of disinterest.

How often were two people head over heels with each other and both of them afraid of bringing up exclusivity too early to a point the other party interpreted it incorrectly? How many relationships fail to set sail because people are downplaying their interest as though it is productive and attractive, only to result in both parties giving each other mixed signals?

That sounds like bullshit!

It wasn’t until I found someone that wanted to be with me and be cared for by me as much as I wanted to care for them that I realized how much I had held myself back from just being my genuine, caring self. I had built up so much fear that I was love-bombing women that I withheld showing my genuine capacity to show love at all.

And that was bullshit!

That’s where I recognized the line between accepting information as ideas and perspective versus just playing monkey see, monkey do with my dating life. People will eat that shit up, though and they think 21 psychological tricks this one blogger told them to do can make any girl their girlfriend fast.

There are no 21 psychologic tricks to make a girl want you badly because you can’t make a girl do something she doesn’t want to do in the first place. And who the hell wants a relationship rooted in psychological influence?

Yet, that’s the bulk of dating advice.

Somebody did something and got some results and decided to write about the cause and effect of it from a position of superiority on the topic. People, in desperation, flock to do the same expecting similar results, often passing along cash for access to “secret wisdom” that’s going to “get them laid tonight” and so much of that is just snake oil bullshit.

Just Be The Best You

So even as you read this very blog, be careful about acting out based upon how some blogger (me) decided you should act because what worked for me isn’t necessarily the key to what is going to work for someone else.

Want an opinion on when to date after divorce? Cool.

You want some new ideas to make your Tinder profile stand out? Awesome.

Want to know why I don’t think you should be a girl’s doormat? Get perspective.

Just always remember that is all dating advice can ever be – perspective. Selling it as a “rule” is bullshit.

The only thing that might not be bullshit is that no matter how much frustration you have faced, you might always just be one more swipe, one more introduction, or one more frustrated rejection away from what you’re looking for. So if you want to obsess over anything, obsess over just continuing to put yourself out there and doing so as the very best possible version of you because it only really matters if you don’t lose yourself in the process.

That’s the only rule to follow: be you.

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Hi, I spewed out all the shit you just read! I like long walks on the beach (but I'm mostly surrounded by cornfields), challenging the status quo of the dating scene, fucking all the rules of dating and encouraging men to live their best life. When I'm not trying to keep the lights on around here and raise two little girls, you can find me drinking and partying - you know the key Wallstreet success...ballin'.

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