Online Dating Tips for Men: 4 Unbreakable Rules for 2020

Three months ago I met this woman for a first date at a coffee shop in San Francisco, but what I did not anticipate was the priceless online dating tips for men that would come out of this experience.

We met in the evening, around 2:15 pm-ish.

Fellas, if you are going to ask a woman on a date, plan it. Asking her what she wants can be a huge turnoff. 

Here’s an example:

Right: “Let’s meet at [INSERT PLACE] on [DAY] at [TIME].” 

Wrong: “What do you want to do?”

Make sense?

Anyways, her pictures were literally jaw dropping. Beautiful waterfall-style golden hair, ocean colored eyes, and a body that would make an hourglass resentful.

I arrive to the coffee shop a few minutes early and scoped out the joint.

What I’m looking for are escape routes, tunnels, and basements to hide in just in case she doesn’t look like her pictures and I want to get the hell out of there. Kidding, kidding. 

The inside of the cafe was chill and had great lighting. The sun, the energy, the ambience. It just made sense.

Online dating tips for men ideal first date location: coffee shop.
Blue Bottle on Sansome St. in San Francisco


I turned my left wrist and glanced at my watch. It’s 2:03 pm, but she hasn’t shown up. 

Do I send a follow up text? Do I wait? (I start talking to myself).

I opted to wait.

Another few minutes goes by and then I get a text from her: “I just got off Bart, see you soon!”

Goosebumps have OFFICIALLY kicked in.

I’m not nervous, but when you never met someone in “real life” before, you don’t know what to expect. Your mind has a strange way of asking itself a million questions.

I sit on the flimsy antique white chairs inside and start doing what everyone does while they are waiting for someone: Scroll through Instagram.

scroll through instagram
Scrolling through Instagram

Then, all of a sudden, I see a figure walking towards me from about 50 yards out.

I raise my head slowly and notice that this person kinda looks like her, but eh, not really. I tilt my head back down again and go back to Instagram (I hate how addicting that app is).


“Hey, Payam!” 

I slowly raise my head while holding my phone in my hand.

“Oh…hey.” I replied.

Holy shit! This can’t be her, she doesn’t even look like her pictures! 

My thoughts went from being excited and hopeful to now figuring out HOW IN THE HELL I was gonna MacGyver myself out of this situation. 

(For you millennials that don’t know MacGyver, he’s pretty much the coolest fictional character ever created. Pretend for a moment and imagine if Albert Einstein and Tom Cruise had sex. Well, MacGyver would be their baby.)

MacGyver looking cool as hell
MacGyver looking cool as hell

Now, the glass-half-full version of me begins to find the positive of this annoying situation. 

Maybe she could be a good business connection? A friend?

The reality is that as best as I tried to enjoy the date, it sucked. Not only does this woman not look like her pics, but her personality just didn’t click with mine. 

I officially wasted my time. One of my major pet peeves. 

Payam 0 – Online Dating 1

Going through this experience taught me a few lessons. Online dating tips for men that want to change and get more dates. Here’s what you’ll discover:

First, I’m going to challenge your thoughts and share the catch-22 of the whole online dating fad.

Second, I’m going to give you the cardinal rule. Break this and you might as well burn your time.

Finally, I’ll conclude with some actionable advice to ensure you never have the problem that I encountered.

Do you accept these terms & conditions? If so, please sign on the dotted… I’m joking. Read on.

The Catch-22 of online dating tips for men

Look, I have a confession: I’m not a big fan of online dating. If you followed my material for a while, you probably know this already.

However, I also understand that not all men live in or near a big city where they can practice the approach or maybe they are apprehensive with small talk and aren’t ready to make the leap. 

That’s cool, but realize that you will learn 5x quicker if you delete the apps, even if it appears you aren’t making progress.

Don’t believe me? Remember the fable The Tortoise and the Hare? If you grew up in the United States, I’m sure you have heard of this story at some point.

Tortoise and the hare
Tortoise and the hare

(Here’s a short video clip if you’re interested)

Long story short: while the tortoise was slower in the beginning of the race, he eventually won the race against a much (seemingly so) faster opponent. 

While your progress may seem slow with discarding the apps and learning how to converse in person, you will prevail in the long run if you keep up with the consistency. 

Online dating is a risk and it’s frustrating if you waste your most valuable asset — your time.  So even if you aren’t sure where to start or the discomfort is too much to bear, try going for small wins instead.

Watch the 5 min video below to see how you can do just that:

Now at this point in the article, you may be thinking, “Why the fudge is this guy knocking online dating? I came here to fix my profile you douchebag.”

I get it. I can be a medium-douchebag at times, but I want to help. My goal is to put your best interests forward and I wouldn’t be doing that if I didn’t tell you what I believe will help you grow the fastest. That’s actually one of the things I’m most proud about DTFSG.

I give it to you fucking straight, nothing held back. 

And hey, that style may not be for you and if it’s not, that’s cool! I’m not for everyone

I appreciate you reading this far, but feel free to close this browser tab if my flare rubs you the wrong way.

Ok, enough of my yapping, let’s get to some juicy advice.

Online dating tips for men (Payam’s cardinal rule)

I like rules. They provide structure and give you a formula to work with. Here’s my golden rule for online dating for men:

If I decide I’m going to meet someone in person, they better (1) look like their pictures, (2) be as engaging as I thought they were through text, and most importantly, (3) be normal.

How many times have you gone on an online date only to come out of it and think, “Well, that was completely pointless. I would have preferred to eat brick.”

Let me show you how I figured this out.

Tips for online dating apps (4 Unbreakable Rules for 2020)

Here’s 4 unbreakable rules that will help you virtually guarantee you have some success on your next online date.

1. Call or do a video call session beforehand

This is absolutely king. These days texting is deceiving and some people are naturally GREAT texters, but are TERRIBLE in person. 

You can confirm your hypothesis about this person with a 60 second call. Well worth it. 


I know what you’re thinking. 

“YOU want me to call them randomly out of the blue, Payam?!” 

Yes, I do. But if you feel weird doing that, give them a simple heads up.

Just text and say, “Hi NAME, I’m gonna call you in a bit.”

Bravery = Sexy

2. Plan an activity 

Who the hell told you to do dinner on the first date? 

Not only is this a bad first date in general, but are you really about to sit down interview-style with a lady you never met for two hours eating full-blown spaghetti and watching each other eat with tomato sauce all over your face? ]

Go for a walk, visit a museum, grab a cup of coffee/tea, go bowling, visit an art-walk, etc. My point is to do an activity together. You’ll learn more about the other person and have better conversations, than learning just how they eat.

3. Lower your expectations

These days you don’t know what anyone looks like anymore. My advice would be to lower your expectations until you meet her in person and then you can formulate a conclusion.

4. Don’t overthink your profile

I know there’s a plethora of articles & tactics on what you should say, wear, and write on your profile. 

Just be yourself. 

Because as soon as you try to portray someone you are not, the real you will come out eventually and then guess what will happen? You break up.

If you aren’t into drinking, why do you post a picture of yourself in the bar? No need. Stay you. For example, I like hiking, so I have a hiking picture on my profile. If she doesn’t like it, oh well.

Picture of me hiking
Picture of me hiking (Follow me on Instagram)

So if you like to sew in your free time, that’s cool. Put pics of that shit up.


The point I’m trying to make with this article is that while online dating has its advantages, don’t become dependent on them. 

Use them, boost your confidence, find out what you want, and then delete them

Or they will delete your confidence.

What online dating tips do you have that I didn’t list? Share them below.