How To Confidently Date Women You Want

When it comes to dating, most people don't have as many options as they'd like. Level with me. What are my chances?

Not good.

Or the options you do have? Feel like settling and you have this nagging feeling that you want to do better. Then you see someone who consistently dates out of their league. How do they do it? In this video, we'll break down the start to several unlikely celebrity couples and use them to show you seven tips to help you date out of your league.

So you're telling me there's a chance? Yeah.

Later in the video, we'll explain why leagues are problematic. But for now, assume out of your league refers to anyone you believe is above you in attractiveness, wealth, fame, or social status. We'll be focusing on men interacting with women, since that's my own personal experience. But similar principles will apply no matter who you like. Okay, so let's start with a few examples that have one thing in common. See if you can guess what step one is for dating out of your league.

You go to one of those Saturday.

Night Live after parties where all love is born.

And I met the love of my life here.

And Ariana, your fiance. The first time you appeared on Saturday Night Live, she was the guest singer? I guess.

Yeah.

Okay, so Saturday Night Live comedians date out of their league. Who? Who else tends to? There are plenty of photographers who aren't rich or famous, but date incredibly attractive models. And it's not uncommon for backup dancers to date out of their league. With examples like Chris Judd and Jennifer Lopez or Jorge Santos and Cristina Aguilera. What do they all have in common? They have access. Simply put, most people never even have a chance to talk to JLo, let alone guarantee hours on set together. So what's the advice here? Picking your career just to meet more people is a bit extreme. But there's another easy way to improve your access to people who are out of your league. Listen to how Kevin Federline met Britney Spears when she was the world's biggest pop star. So you just met her.

How? Mutual friends.

Out at the club, Kevin wasn't just some random guy. He was friends with Britney's friends. A common mistake guys make when trying to improve their dating lives is to only talk to people they're attracted to. But when you go out, you're much better off talking to everybody. For starters, it's more attractive if someone sees you at the center of a bunch of people telling stories and making them laugh, rather than stalking alone around the venue. And you never know when you'll make A random new friend who ends up transforming your social life. One other quick point on access. While you don't want to pick your career just to meet people, if you're genuinely interested in something, but you worry your friends will tease you for it, like taking dance classes, if you're a straight man, do it anyway. Otherwise you're not pursuing an interest you may love. And you're guaranteeing you don't have access to the other people doing it. But access alone won't get you far. If someone is high status or extremely beautiful, even if they aren't a celebrity, they have had hundreds, possibly thousands of people approach them trying to date them. So you have to stand out from the average person who approaches them. For instance, in her heyday, everyone who saw Britney Spears would freak out, trying hard to get her attention.

I would do anything just to get a glimpse of her in person. I'm gonna be shaking, nervous.

Contrast that with how she describes Kevin's demeanor when they met, and you can start to understand why she was attracted to him.

He was very, very mysterious. He just seemed not fazed by anything. And I saw her as a normal person, you know, I never treated her any different than any other normal person.

Kevin didn't treat her like a fan. For a woman like Britney, who's used to men throwing themselves at her, that unfazed attitude set him apart from everyone else and made him attractive. That said, simply being unfazed isn't always enough to attract someone. So let's go through three specific ways you can stand out in a positive, attractive way. The first is by playfully teasing. This is a great flirting habit in general and is especially great if someone is used to being surrounded by yes men and flatterers. Here's a few quick examples with Craig Ferguson teasing women he's attracted to.

I have to say, I'm from Newton Mearns. Oh, that's the posh part of Glasgow that's. She made. She wanted to make sure. I said, yeah, it's very posh. That's like saying, oh, yeah, I'm from the hood. And then you go, which part? And you say, Beverly Hill. Doing that to me, you're saying, freaking me out. I'm putting spells on you. Yeah, you've already done that. You did that when you did the knee. That's right. You see me move back like that. I did, yes. Crawling away. No, no, distance is hurting me.

No, it's.

Listen, it has to be very cold. Don't you do well in the cold?

I mean, I like snow for like A minute.

Like I love to ski, but like see, that's not skiing. This is not skiing. Ski. Yeah, yeah. This. Yeah. I don't know. I'm not sure that skiing either.

Here's one more quick example with Katie and Russell from right before they started dating. The footage isn't great quality because it's behind the scenes footage, but. But you can see their banter is far from non stop compliments. If you like the idea of playful teasing, but you worry about coming off like an asshole, check out our video featuring Craig Ferguson about how to confidently flirt with anyone. It lays out some ways you can playfully tease and feel confident you'll get a laugh. We'll link to it in the description and at the end of this video, playfully teasing someone of high status or beauty does two things at once. It makes them laugh, which builds rapport and it also helps you stand out compared to the exclusively complimentary people who are scared to say anything the person won't like. There's absolutely nothing wrong with the occasional compliment. Compliments can be flattering, but if all you do is compliment someone, it can be off putting. For a bit of a cringey example, imagine yourself as Britney in this next clip. Who the flowers for?

They are for Ms. Britney Spears, the one and only Britney. I love you. This is an honor just to even be standing in front of you. I'm a huge fan. This is a dream come true to even be so close to you.

Being overly complimentary isn't the only way you can accidentally make yourself less attractive to someone. Another common mistake is saying what you think they want to hear. For a common example of how people act subordinate to people they admire, check out the scene from the movie Trainwreck. It's a joke, but unfortunately it's not far off from what a lot of real conversations look like. When someone's trying to make someone else like them. You follow sports?

Oh my God, sports. I love them.

Who are your favorite teams?

I like smaller teams like the. Not the big leagues. I like the like Long Island Mediums, the Acorn Pine cones.

If your version of being nice is to be agreeable no matter what, you should stop. This won't build attraction, especially with someone who gets treated this way by everyone. In fact, if you want to be attractive, do the opposite. Prioritize being honest above saying what you think they want to hear. If they're extremely attractive or high status, this will instantly make you stand out from most people in their lives. Watch this for a great example with Kevin and Brittany. This is very soon after they first met.

How do you feel about marriage and commitment? I feel that love is love, Love has love. I don't believe in marriage.

You can hear the disappointment in her voice. This was clearly not the answer she was looking for. But this honesty only made her more attracted to him.

I kind of was playing reverse psychology. I don't like you, so I'm gonna ask you about marriage, you know? So I think that's why I probably did all that, which really screwed me, because I ended up falling for him even more.

This was doubly attractive because in addition to being honest, it makes him a bit of a challenge. Flirting with someone who's hard to get can be fun. For someone who's used to everyone always being available to them, the number one way most people screw this up is by doing the opposite and being available at all times. If you want to be attractive, don't treat someone you've just met like they're the only good thing in your life. It's a bit of an extreme example here, but listen to how Jason Sudakis hooked Olivia Wilde by not showing the intense immediate interest that most men were giving her at the time. It was just really, like, cool.

He played it really cool. Once we started, like, texting a little.

Bit, really witty texts, right?

He got my number. He didn't text me for a month. I was like, this is incredible. Oh, my goodness. Oh, you must have been on the.

Hook, just like Brittany. You can see Olivia was hooked by the fact that Jason was a challenge to get. Now, it's important to mention here, neither of these last two examples was done to be a mind game. Kevin genuinely didn't believe in marriage at the time, and Jason simply had other things going on. Listen to him explain as much to Stephen Colbert in this next clip. I just didn't make any sort of moves, you know? Is that the trick? Show no interest? No, just don't. I think so. You hear that sometimes, but all I did was, like, I was just very, very busy with other things. A lot of dating advice you'll see online is about finding attractive behavior and trying to copy it without modeling where it comes from. And when you just copy the behavior, you can end up coming across as fake, which will blow any chance you have with someone. So instead of trying to fake it, the key is to genuinely have other stuff going on in your life. This will automatically make you behave more attractively. For instance, most people without much going on in their life are attached to their phones, so they see new texts right away. Then you stress about artificially delaying your response so you don't seem needy. But if you're out surfing in the ocean or playing guitar in a jam session with friends, you won't have to worry about how long you should wait to text someone because you won't even see their text for hours. So build a life where this random person you just met isn't the best thing in it. Then you'll naturally do the most attractive thing. Also, it's important to note you don't have to wait a month before you ask someone out or hide your romantic intentions. Here's Russell Brand as a counterexample. Both of these clips are from before he and Katy started dating.

It's pretty clear I'm supposed to say that music is the real winner tonight. But Katy Perry didn't win an award and she said staying in the same hotel as me, so she's going to need a shoulder cry on. So in a way, I'm the real winner tonight. Thank you very much. Actually, this is an item that I like to call flimsily veiled excuse to chat up a woman by getting her on the radio show. And you're in the middle of that now.

It's pretty obvious that he's into Katie, but even still, Russell doesn't act like getting Katie is the most important thing in his life. In this next clip, Katie seems open to his flirting, but Russell doesn't immediately jump on it and act desperate to make it happen together.

Boys. I know rambunctious boys over there. Quite rambunctiously. An hour flight. I will come over there.

Uh oh. He shouldn't have said the word.

That's the kind of friend.

She said the worst. He said two words.

Yeah, she said it. It's all out there. Katie, remember them VMAs. What we done.

As a tangent, Russell's flirting is so well received partially because of his Persona. He flirts with everyone, so even when he's directly hitting on you, it can be hard to tell if he's actually interested. So what is your secret?

My secret is that I know that within you there is a limitless divine beauty. And within me as well. And if I connect with that, then we'll be okay. And you as well. And Chris, for God's name.

Okay, so playfully tease. Be honest when it's scary and don't immediately prioritize the person above everything else in your life. Well, how are you supposed to do that when just standing near the person probably makes you nervous? The first thing to do when you're nervous is recognize that being nervous isn't a character defect. Everyone gets nervous from time to time, even Russell Brand.

I was anxious and nervous on the date. Normally, like on first dates, I'm alright because first date for me used to be the only date. Right? Right?

Yeah. That said, there are a few things you can do to minimize your nervousness if you're meeting someone for the first time, either because you see them at an event or because it's a blind date. One trick is to warm up socially before you talk to them. Turning on your charisma at a moment's notice is a skill and not everyone is naturally good at it without practice. If that's you, then don't make the person you're intimidated by the first person you speak to at an event. Warm up by talking to your Uber driver. The bouncer, the bartender, the hostess. Really anyone who's around. Get into a talkative mood and you'll find it way easier to start speaking to someone you're attracted to. Second, if conversation goes well and you exchange information, don't spend time on their social media. Social media plays a big role in convincing you that someone has the status, power or otherworldly filtered looks that make you feel like they're out of your league. And third, have standards beyond fame, wealth or beauty. The average person's internal dialogue when talking to someone attractive is I hope this person likes me. Having standards means that part of the conversation is meant to genuinely see if you like them. You'll instantly feel more confident once you stop treating conversation like a one sided tryout. This will help your nerves and help you be more attractive. It will also help you avoid relationships that ultimately make you miserable. A good question to ask yourself right now is what personality traits does someone need to have to be in your life? If they don't have status, wealth or good looks, then don't let anyone into your life if they don't have those traits, regardless of their status, wealth or good looks. This is helped tremendously by recognizing that ultimately dating out of your league is a bad goal. Often the goal to date someone out of your league comes from insecurity. A good way to test this is when you think about dating this person. Do you think about how you would enjoy their company or do you think about how great it makes you look or how cool other people will think you are? There's nothing wrong with dating someone who's beautiful or wealthy or famous. But if you prioritize dating out of your league over dating someone that treats you well you're setting yourself up to be miserable. That said, finding the right person can be hard if you aren't good at presenting yourself. If you're someone who has few dating options, it can be very tempting to settle for the best you can do, even if you know they aren't really that great for you. If you want to learn how to be more confident and attractive in conversation so that you can have options and never have to settle, you may like our program Charisma University. It's a step by step guided program that will show you how to have a magnetic presence when you walk into a room, enter any conversation with confidence and make an amazing first impression on anyone you meet. It takes just 20 to 30 minutes a day and each day comes with a daily action guide so you know exactly how to put everything you're learning into practice. And it's sequential with each day building upon the last. It also comes with a 60 day money back guarantee so the only way you pay anything is is if you think it was worth more than the money you invested. I could go on about the program, but rather than tell you what I think, let's take a look at what some of the members have said about their experience after the program. The first one comes from a guy who says CU helped his dating life. He says, firstly loving the course. I have cherry picked a few things, for example the filter lesson in the conversation module. This one lesson completely changed my life. I've liked a girl for a year now but never thought much of it because I thought she was too pretty. Took your lessons, gave things a shot and now we're dating. This next one comes from a guy who is interviewing for new jobs. He says, I interviewed at dozens of places for jobs after medical school. At the end of one of my interview days the doctor pulled me aside and said that I had hands down the best interview out of everybody and that they would love to have me at their program. They ranked me number one and it's my current job. And this last one is a comment in the course from someone who used it mainly to improve their dating life and he says life changing in six weeks I went from being socially awkward with few friends to the life of every event I attend. I also went from having serious girl problems to dating the girl of my dreams. Charisma University transformed me from a lonely introvert hoping to better connect with people to an energy filled extrovert who makes new friends everywhere I go. And there are more success stories just like those in the comments. If you decide to join the course. If you want to check the course out, click the link on screen now or below in the description. We've had thousands of members go through the course and get a ton out of it, and I would love for you to do the same if this is an area that you care about. Either way, I hope that this video has helped you and I look forward to seeing you in the next one.