7 Things “Nice Guys” Get WRONG with Flirting

Dating> Flirting > Flirting Mistakes
by Bobby Rio • Updated: September 1, 2022

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flirting mistakes

Avoid These Flirting Mistakes

Why is it that some guys can talk to a woman for just a few minutes and get her feeling excitement, chemistry, and attraction?

Why is it that other guys can spend a whole night with a woman and leave her feeling nothing?

Later that week, when that guy tries to get her out on a date, he’ll find that she’s not available, she’s busy, or she tells him she’d rather be friends.

It all comes down to FLIRTING.

When I was growing up, I had the unfortunate circumstance of being both a nice guy and an introvert. Conversation didn’t come naturally to me, and when I did get the courage to go talk to a woman, I veered into the “nice guy” realm where everything I said fell flat.

I was never able to create that attraction. And was making all the flirting mistakes we’ll discuss hre.

So over the years, I had spent a lot of time studying that other type of guy. The guy who can walk in, open his mouth, and the girl is instantly pulled into the conversation.

You can tell when a girl’s into it because she’s leaning in towards the guy and she’s laughing and she’s touching him.

That’s when a guy’s flirting skills are in place.

Seven Ways “Nice Guys” FAIL At Flirting

Compare that to the nights where you get a girl on a date but there’s a disconnect there. You feel like she’s almost just trying to get through it.

Maybe it even reminds you of when you’re out with an acquaintance you don’t like. Maybe you’re stuck at a family event. Or a “bonding with your coworkers” outing. You know the conversation is going to suck but you’re in there anyway.

That’s what “nice guy” conversations feel like to a woman.

Then the “nice guy” blames it on everything else when things go wrong. When he doesn’t get a second date, he starts thinking, “Oh, it’s because she’s into another guy.”

In actuality, if he had created that connection and chemistry through flirting on the date, he wouldn’t be experiencing that.

It’s time you understand the major flirting mistakes that “nice guys” make that cause a women not to want to be with them.

Flirting Mistake #1:  Missing Intention

This is when a nice guy meets a woman and he doesn’t know where he wants the conversation to go.

He has no intention.

A nice guy starts talking to a woman at a party. Or maybe he’s on a date with her. But he doesn’t know where he wants the conversation to go.

And when you don’t know where the conversation goes, you don’t have an objective.

When a nice guy gets in front of a beautiful woman, his only goal in a conversation is, “I want her to like me.” So his whole framework in his mind is: “What can I say to get her to like me?”

Example of Having Intention

On the other hand, a guy who’s good with women will know exactly what his intention is when he sees a beautiful woman at a party.

He’ll think,

  • “I’m going to get her number,”
  • or “I’m going to see if I can leave the party with her.”

Once he knows what his goal is, he’s able to plant seeds towards that goal early in the night and give those seeds time to grow. There’s going to be a momentum in his conversation. He’s going to be saying and doing things that all build upon each other to further him towards his goal.

It’s the same way almost anything in life works better with a plan.

If you get in your car and just start driving, no destination in mind, what are the odds that you’re going to end up in California? You’re just as likely to do laps around your city for days, or to end up in New York.

On the other hand, if you set your GPS to California, every mile you drive is moving you consistently towards the Golden State. After 3 miles, you might not see a difference, but after 300 miles, you’ll be aware that every turn has been taking you farther in the same direction.

Now instead of California, set your GPS towards the goal you want with a woman.

Setting Your Intention with a Girl

  • So, if your intention is to hang out with a girl again, you’re going to plant seeds throughout the conversation to bring that back. You’re going to talk about activities you both like to do, you’re going to find a roundabout way to discover her availability.
  • If your intention is to invite her back to your place that same night, you’re going to plant seeds about the cool dog that you have back at your house who she’s just got to meet. Or you’re going to plant seeds about your wine collection and how she’s got to taste this new wine you just got.

This is possible because you have an intention. You have a direction.

So, when you get in a conversation, ask yourself: what is the destination I want to get to?

If you don’t do this, you’ll end up like the nice guy whose only destination in mind is, “I want this woman to like me.”

He starts spinning his wheels and getting nowhere because everything he does actually causes the girl to NOT like him.

Even if the conversation starts off good at first, it’s always going to fizzle out if he doesn’t have a destination.

The girl will walk away and he’ll be left, thinking, “I thought she was liking me. What happened?”

The sad truth for him is that she walked away because he wasn’t leading the conversation anywhere.

You need to be thinking, “Where am I leading this?”

Am I leading it to get her phone number, am I leading it to invite her back, am I leading it to try to kiss her in a little bit? You’ve got to have that in your mind.

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Flirting Mistake #2: Qualifying Yourself

Qualifying yourself to a woman is one of the deadliest flirting sins.

It’s when you subconsciously believe that you are below a woman and that you’re lucky to be with her, so you actively try to convince her that you have value.

It’s doing and saying things to convince her that you’re cool.

Even if she likes what you say, you’ve already lost.

Because you’ve put her in the role of the JUDGE and you’ve put yourself in the role of the PERSON ON TRIAL.

You’ve cemented the idea that she’s above you and that she gets to decide whether you measure up.

That’s incredibly unattractive.

Example of Qualifying Yourself

Maybe she brings up how she recently got back from a vacation to Mexico. She says, “Oh, I was in Cancun last week and we had such a good time.”

A “nice guy” hears that and thinks, “Oh, she went to Cancun. Where have I been recently that I can tell her about? I need to make myself seem important and cool.”

So maybe he says, “Oh yeah, I was in Vegas last week and I did this and this and that.”

Even if the words you say are all logically telling the story of a very cool life, the woman senses what’s going on underneath the surface. He’s trying to qualify himself.

But the bigger issue is that he’s missing an opportunity to qualify her and say, “Oh, tell me a little bit about Mexico. What made you go down there?”

After he asks that, the woman is going to start qualifying herself.

That’s right, you need to TURN THE TABLES on a woman and get her explaining why she’s cool, or why her decision made sense, or what kind of trip she actually took.

When she puts effort into answering these questions, she’s putting you in the role of the judge and putting herself into the role of the person on trial.

 Stop thinking, “What can I do to make her think I’m cool?” and start giving her a chance to work to impress you.

How to Qualify a Woman

@bobbyriocoach here’s another way to “test’ where you stand with a woman #datingtipsformen #datingadviceformen #bobbyrio ♬ original sound – Bobby Rio- Dating Coach 4 Men

Flirting Mistake #3: Being too PG

When I say, “PG,” I’m talking about movie ratings. There’s PG, PG-13, and R.

When nice guys talk to a woman, they often revert back to acting like a character in a Disney movie.

They act like they’ve been rated PG.

If you’re ever flipping through channels and you land on a PG show, the conversations on the show will be very cookie cutter, very safe, very generic.

But if you watch an HBO show that’s rated R, it’s a totally different vibe. It’s edgy. There’s a reason kids aren’t allowed to watch it.

Flirting Should Be R-Rated

Well, when you’re talking to a woman, you’ve got to have a rated R conversation. An adult conversation.

But “nice guys” tend to revert back to that PG rating, where they’re talking about puppy dogs and ice cream, and they’re kind of afraid to bring anything edgy into a conversation.

Now, sometimes you get lucky and the woman makes a comment, she makes a comment about a party she went to and got drunk, or she makes a comment about something vaguely sexual.

And then the nice guy goes, “Oh, it’s okay for me to be a little edgy.”

I call it the Rated R Switch, the moment when someone leads the conversation across that threshold into R-rated territory.

Don’t wait for the woman to make that switch. If you do, the underlying vibe will be that she’s the daring one and you’re playing catch-up. You want to take control and lead the conversation.

Don’t get stuck in that Disney Channel boring, safe, predictable conversation too long. That doesn’t elicit strong emotions, it doesn’t give her that excitement, that attraction, that chemistry that we talked about earlier.

Flirting Mistake #4: Failing Women’s Tests

A test is a woman’s way of figuring out if a guy for real.

It exposes whether he’s really a cool guy, or just pretending.

Does he really get girls and is he really experienced? Or is he actually just a loser who knows how to put on an act?

Women can’t afford to waste time with a loser. So they look for clues. They ask themselves, “Is this a guy that other women want?”

But when they’re still not sure, they start saying things and subconsciously seeing how you react.

Some examples of Failing “Tests”

  • When a woman makes a subtle insult to you.
  • Maybe you’re wearing a hat and she’ll say, “I don’t really like guys that wear hats.”
  • Or she’ll be on a date with you and say, “I’m not going home with you tonight.”
  • She could test you by saying something overly sexual and seeing whether you jump on it in the wrong way and end up getting creepy on her.

In all these examples, she’ll be seeing if you take the bait. She is trying to get a reaction out of you.

In order to pass a test, you have to be NONREACTIVE.

Let the woman see the tests roll off of you.

So if she says, “I’m not going to sleep with you,” you don’t want to automatically start going, “Oh no, I wasn’t even thinking about it.”

Because then again, you’re qualifying, you’re explaining. She sees that she totally threw you off your game and that’s not attractive.

But if she says, “I’m not going to sleep with you,” and a guy responds, “Of course not. We’re not having sex,” very calmly and dismissively, then changes the subject, that’s going to get her attention.

This is because the emotional content is most important, and that guy’s emotions remained totally unaffected as she threw an obstacle at him.

With any test, the guy who passes it is the guy who underplays it or doesn’t even acknowledge it. You’ve got to be cool in the face of adversity. If you have a large emotional reaction to a test, you’ll fail it.

More On Female Tests:

Flirting Mistake #5: Not Breaking Rapport

Rapport is when you’re getting along well with someone in a conversation.

You’re vibing together, having things in common, agreeing with each other. Even complimenting each other.

It’s something that you want to create early in a conversation.

You might say, “Have you travelled?” and tell her a few places you’ve been.

Then she’ll say, “Oh that’s cool, I’ve been there, too,” and then she mentions a restaurant she liked in that city. You say, “Oh I love that restaurant, too.” You two are firmly experiencing rapport.

A “nice guy” will try to keep this going forever.

That’s his biggest flirting mistake.

“Nice guys” are scared to end rapport.

The problem with that is that if you stay in rapport, you never actually transition.

We talked about having an intention, and a lot of conversation is about knowing how you’re moving things forward in the direction towards your intention. Every time you’re moving it forward, we call it a TRANSITION.

If your objective is to have her physically attracted to you, wanting to have sex with you, then you can’t stay in that comfortable rapport all night. At some point, you’ve got to end that.

If you’ve just found out that you have something in common and she says, “Oh I love that restaurant, too,” you can break rapport by saying, “You like that too? You are either the coolest girl in the entire world or you’re a complete weirdo.”

Say it in a way that is a little impudent, a little cheeky, a little off-kilter. You don’t want it to be mean, but you want to throw her out of that comfortable rapport and get her working to impress you as you transition. A conversation has an intention. Breaking rapport is a critical aspect of moving things along.

Flirting Mistake #6: Confusing Complimenting with Flirting

When guys tell me how they had a date with a girl and they wound up in the friend zone, and I’ll say to them, “Were you flirting with her?”

Too often the guys will say, “Oh yeah, I told her she had really nice eyes. I told her I liked her perfume.”

What those guys are doing is complimenting. It’s all positive. It’s all even-keeled.

On the other hand, flirting is far from even-keeled.

Flirting is tension and release, pushing and pulling.

Flirting is when you tease a girl.

When you say something like, “Oh, you’re the best. Get away from me,” she knows what you’re doing.

It’s sort of a secret language.

“Nice guys” don’t pick up on this naturally.

Nice guys are conditioned to think that you have to be nice, compliment her, and tell her you like her.

Then you see some guy at a party totally teasing a girl, busing on her, and she’s laughing at him and acting like she’s all over him.

That’s the secret language that women speak, and you must able to speak it, too.

You can’t think, “Well, I told her during the course of a conversation that she had a really a nice ring on and that I thought she was funny, why doesn’t she want to have sex with me?”

Because that’s complimenting, not flirting.

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Flirting Mistake #7: Having No “Bits” to Use

In many ways, this one is the most important.

Some guys in life are what we call “NATURALS.”

They grew up in such a way, and had the right role models, so that they can just effortlessly attract women.

Back when I was a “nice guy”, I had several friends who were naturals. I used to watch them and try to figure them out.

I would see them tell the same story to multiple different women on multiple different nights.

Each girl heard the story only once, but I’d hear the story every night as the guy repeated his routine.

I’d be like, “Man, he was telling that story to the last girl that he talked to. That’s so lame. He can’t think of anything else to say.”

I criticized it back then, until I realized the value of having a “bit.”

Have Stories Ready

A bit is a short story that you can easily weave into a conversation.

It’s valuable because it’s already been perfected and tested on other women, now it can keep cranking out results for you.

We talk about a conversation. It’s got point A, point B, point C, and point D.

You’re trying to take things from the first “Hi,” all the way to your end goal.

Well, there’s certain things that work to keep moving that along. When you figure out something that works, you want to keep using it.

Jon Sinn teaches something called the Strawberry Fields Routine.

It’s a cold-reading game that he plays with girls. He told me one time, “I literally used this thing on a hundred dates and every single time, it worked.”

The Strawberry Fields Routine is designed to create a more sensual frame. I started teaching it to my clients and they started getting the same results that Jon got.

When you start playing this game with a girl, you’re moving the interaction out of comfortable rapport and onto a more intimate and R-rated level. It accomplishes a huge transition in the interaction, one that could be tricky to pull off if you’re just winging it.

So having that one bit already perfected takes a lot of pressure off and allows you to accomplish the transition naturally.

My “Bit” for Explaining My Job

I used to have something I called the Painting Houses story.

I used to work as a painter. I knew that at some point on a date, a girl was going to ask me, “What do you do?” I never had a good answer for it. I would give a bland answer, “I paint houses but I don’t really like it,” and it would kill the momentum of the date.

So I decided to plan a better answer. I decided to create a bit.

In all my days of painting houses, one memory stands out above the rest. It was the time I opened an old lady’s closet… and found a bag of sex toys.

The bag fell to the floor. Then JUST as I’m putting it back in the closet, the old woman walked in. It was so embarrassing and awkward that it became a pretty juicy story. I began telling this story as a bit every time I was asked what I did for a living.

This bit accomplished several things:

  • It took the attention off of my job, so that I wasn’t stuck talking about a job I wasn’t passionate about.
  • It brought in some humor.
  • It introduced an element of sexuality, making the conversation R-rated.

Once I had flipped that Rated R Switch, I was able to transition and flip the question onto the woman. I would go, “What about you? If I was painting your house, what I would I find in your closet? I bet I would find some freaky stuff.”

Having ready-to-go bits like that is something that is very, very, very important.

Most nice guys don’t think of it. They go into every conversation like it’s a completely new conversation. Don’t force yourself to reinvent the wheel every time. The guys that are really good at this have bits ready.

Recap of the 7 Mistakes:

We talked about seven flirting mistakes “nice guys” make with women.

  • Not having intention.
  • Qualifying yourself.
  • Being too PG.
  • Failing tests.
  • Not breaking rapport.
  • Confusing complimenting with flirting.
  • Not having bits ready.

The “Golden Triangle” of What to Say

If you struggle with what to say, I recommend downloading a copy of my book Charismatic Conversation Secrets, where I provide word-for-word examples of the type of conversations that turn women on.

Avoid those seven mistakes, and be ready for all the excitement, chemistry, and attraction that you used to observe when you saw other guys on dates. Because why should other guys have all the fun?