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How to Approach Women.... and Get Dates Today!

Learn how to approach women: Dating coach Connell Barrett shares 20 tips to confidently approach women and get dates.

Get ready, because I’m about to give you the approach opener that works 89% of the time! (Yep, I’ve tested it.)

But first, I’m gonna read your mind. Here goes.

I’ll bet that you often see attractive women you’d love to meet—at the gym, in bars, or maybe at the grocery store. And you’d love to confidently approach them and get dates, right?

But something holds you back, and you rarely (if ever) approach. You’re not sure what to say, and you don’t want to come across as creepy. So you feel stuck.

I get it. I used to have the same problem.

It’s frustrating to see attractive women and not know how to approach them. It can hurt your confidence, and lead to a lonely, disappointing dating life.

So, let’s fix this… today! Let’s get you confidently meeting amazing women, and getting numbers and dates.

In this column, I’m gonna share 20 of my best tips to teach you how to approach women, and do it with charm and confidence.

Oh, make sure you read Tip No. 16—the “approach opener” that works 90% of the time!

These 20 tips are from my Amazon bestselling book, DATING SUCKS BUT YOU DON’T, a step-by-step roadmap to confidently approach and attract women.

As I write in my book, “Approaching is about more than just getting the girl. It’s about freedom. To be able to walk up to a woman and genuinely connect is liberating.”

Until you can confidently walk up to a woman and flirt as your authentic self, there’s room to grow.

You’re about to learn how to approach women, so that you can stop feeling anxiety, and start confidently getting dates with attractive women you meet at the gym, grocery store, bar, or coffee shop.

So let’s do it! Let’s learn how to approach women, and get results. Here are my top 20 tips!

How to Approach Women and Get Dates

TIP NO. 1: YES, WOMEN WANT YOU TO APPROACH

You might think that beautiful women don’t want men to approach them, but in fact they’re dying for a solid, authentic man to take that romantic risk… IF he does it with charm, and not like some “pickup” weirdo.

Attractive women get constant attention from men, but usually in the form of leers, wolf whistles, and come-ons from pickup-artist creeps.

Know this: Women don’t want EVERY man to approach them, but they’re dying for a MAN to approach them – a good-hearted, charming gentleman like you. Buy into this! (Take it from me, a guy who’s approached thousands of women.)

TIP NO. 2: ASSUME ATTRACTION

I urge you to believe in advance that a given approach will go well. It’s a Jedi mind trick that’s called “assuming attraction.”

When you walk up to her, assume that a woman will be into you. This positive expectation makes you stand taller and talk louder, often creating a self-fulfilling prophecy. Women can sense that worthiness, that belief, and they like it.

When you assume attraction, you get attraction. When you assume rejection, you get rejection.

TIP NO. 3: EMBRACE “REJECTION”

Good technique is important but overrated. What you really need is to learn how to get “rejected,” but elegantly. Get rejected and laugh it off. Get rejected and feel good for trying.

Don’t take it personally, or else you might end up with more pain and fear than you started with.

There are no quick fixes in the area of approaching. Magic bullets only exist in werewolf movies.

But destroying your fear of rejection is the closest thing you’ll get to an approaching panacea because when that fear disappears, you become free to take action with confidence. And women love confident guys.

TIP NO. 4: HOW TO APPROACH WOMEN—THE UPSIDES 

Link tons of pleasure to approaching, and very little pain.

Right now, you probably link more pain than pleasure to approaching, and that’s what causes “approach anxiety.”

But once you link mostly pleasure, and you see those gorgeous women, your brain will quickly run down the upsides and downsides of approaching, and it will look something like this:

Upsides to Knowing How to Approach Women: 

  • Finding love and connection 

  • Getting a great girlfriend 

  • Growing 

  • More confidence 

  • More dates 

  • Great sex 

  • Expressing your true self 

  • The joy of taking action 


Downsides to Knowing How to Approach Women:

[*cricket noises*]

Link a LOT more pleasure to approaching, and you’ll start getting a LOT more dates.  

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TIP NO. 5: THE NEW WAY TO LOOK AT “APPROACHING”

Every approach is a 10 out of 10, because you either “get the girl” (win!) or you put another brick in your cathedral of your character (win!).

TIP NO. 6: OBEY THE RULE OF ONE IN THREE

There’s a concept called the Rule of One in Three. When you’re Radically Authentic with women, you naturally become polarizing.

I don’t mean in an intentionally dickish way. You just express yourself in a more raw and real style, which many people will love and some won’t. But that’s the point. You don’t want to be kinda liked by most women. You want to be loved by a subset of women.

When you get good at approaching from a truly authentic place, about one out of three girls will be very into you, and two out of three won’t be interested at all, at least in a romantic way. At this point, you’ll get three kinds of reactions:

Be liberated by this! You can brush off the brush-offs. They’re part of the path to finding the women you have chemistry with.

TIP NO. 7: BE AUTHENTIC AND POLARIZING

As I mention in my book DATING SUCKS BUT YOU DON’T, when I first began approaching, I was watering down my personality, being too safe. Lots of women thought I was pleasant and nice, but none wanted to take me home.

Once I grew bolder and more authentic, I started to experience the Rule of One in Three— sometimes in a single moment.

One night, I boldly walked up to three women who were standing at the bar. 

ME: [with confident vocal tonality] “You guys are adorable. I had to meet you. Are you friendly?”

GIRL ON LEFT: “Hey, yeah, we’re friendly.”

GIRL ON RIGHT: “I am NOT friendly.”

GIRL IN MIDDLE: You are cute!”

And I got the middle girl’s number, thanks to the Rule of One in Three.

TIP NO. 8: BEWARE OF EXCUSES

I can’t stress this enough: Approaching will feel extremely scary to you at first, and you will try to talk yourself out of it. You’ll see that Jessica Alba lookalike at the bar, walk toward her with the perfect opening line on your tongue, and at the last moment you’ll tell yourself, “Gosh, I really need to go do my taxes.”

That’s your Lower Self pouring poison in your ear. Do not listen.

I’m not trying to psych you out. I just want you to be ready when your brain manufactures a “good” excuse not to talk to that Wow Girl. Be ready and chat her up anyway.

TIP NO. 9: OFFER AUTHENTIC VALUE


Simply put, be you, and try to make her day/night better than before she met you.

Be sincere and authentic. Crack jokes. Show your playful side. As I said in Ask Men, women want a fun, emotional vibe from men—not a logical energy.

TIP NO. 10: WHAT MAKES HER FASCINATING?

When talking with her, look for things you have in common and share emotional experiences. A former dating coach of mine gave me a great tip that I still use: “Find out what makes her fascinating.” If a woman feels that you “get” her, she’ll feel more connected to you.

Lots of guys want her. You’ll be the guy who understands her, and that’s way more powerful.

TIP NO. 11: GO FOR IT!


If you like her, go for what you want—a number, a date, a dance-floor make-out. Don’t settle for just a nice conversation. Lead things somewhere. It’s about playing to win, rather than playing not to lose.

One summer afternoon, I was wingmanning for my client, Michael, 30, who was on a park bench talking to a woman he’d just met. I left for a few minutes, and when I got back, she was alone. I found Michael sitting not far away, his shoulders slumped, his face in his hands.

“What happened?” I asked.

“I screwed up,” he said. “I chickened out and didn’t ask her out. I just left. I suck!”

“It’s all good,” I said. “She’s still there. It’s not too late. Let me ask you—if you went back over there, what would you say to her if you knew you couldn’t fail?”

He said, “I would tell her that I wimped out because I got scared, but that I’d love to take her out.”


“Perfect,” I said. “There she is. Go!”


He re-approached her, and got her number, date set.

Don’t settle for just a nice conversation. Go for it!

TIP NO. 12: HOW TO APPROACH WOMEN: THE ART OF OPENING

Your opener does not have to be clever or fancy—just good enough to get her to respond. I’ve begun conversations with openers as simple as these:

  • Hi
  • You have great style. 

  • How’s your night going? 

  • I feel awesome today, and I had to share it with you. 

  • What book are you reading? 

  • Is this the coolest club around here? 

  • Whoa, this line is long.

Being clever or funny is a nice bonus, but it’s just not necessary. Simple and clear is best.

My client Oscar was having a drink with friends at a Miami lounge when he saw Anastasia, a tall, intelligent pharmaceutical rep. He approached her, they liked each other, and later left the bar together.

His opener was a simple, “Damn, who are you?”

TIP NO. 13: TRY DIRECT OPENERS

Oscar used a “direct opener,” which means that your words and/or vibe convey clear romantic interest from the get-go. Here are examples of direct openers.

  • Hi, I saw you and had to meet you. 

  • You’re absolutely adorable. 

  • You’re gorgeous. Who are you? 

  • I’m here to flirt with you. 

  • You’re sexy. 


Upside to being direct: There’s no chance of the friend zone. Whether or not she’s attracted to you, she’ll know why you’re talking to her.

TIP NO. 14: BEING DIRECT DOES NOT MEAN BE VULGAR

If you open in a direct way, don’t make it about her body, and don’t say anything about sexual acts. “You’re sexy” is about as blunt as you want to be. 


TIP NO. 15: BE INDIRECT

“Going indirect” means that you don’t explicitly state romantic interest up front. You might make small talk or give her a friendly compliment. You don’t hide your intentions; you just don’t lead with them. Here are some indirect openers.

  • How’s your night going? 

  • I dig your boots/jacket/style. 

  • Isn’t this song great? 

  • How’s that book you’re reading? 

  • Your hair looks amazing. 


Upside to being indirect: It opens the door to a lot more conversations since you don’t get as many blowouts. This helps you gain experience, build confidence, and talk to more women, which gives you more dating opportunities.  

TIP NO. 16: USE THE “COMPLIMENT + QUESTION” OPENER

Here’s my favorite way to approach a woman. It gets a good response and starts a conversation 89% of the time, in research I’ve done with my clients.

And you can use it anywhere, from the gym to the grocery store to the bar on Saturday night.

Give her a power compliment—that’s NOT about her looks—and follow up with a “why” question.

Notice something about her that you like—say, her leather skirt, her tattoo, her pink Chuck Taylors, or confident vibe. And compliment her on that thing. And then ask her a “why” question.

The follow-up question is key, otherwise she may merely thank you for the compliment and go on her way. A “why” question leads to a conversation, which can lead to a phone number and a date.  

Example: You’re at Starbucks on a Saturday afternoon, and standing next to you is a brunette beauty waiting on her chai latte.

Ask yourself, “What do I like or notice about her?” (Umm, besides her curves.) Answer: She has a tattoo of the Eiffel Tower on her wrist. Compliment her on the tatt, and ask her a “why” question about it.

It would go something like this: “Excuse me, miss. I really like your tattoo. Very cool design.” She’ll say thanks. “I’m curious,” you continue. “Why did you choose that design?”

She may reply with something like, “Well, I went to Paris last summer, and the trip changed my life!” Boom! You’re off and running.

“Why” questions are better than “yes/no” questions because they make people dig deeper for the answer, which leads to a more engaging conversation.

The “Compliments + Question” opener works just about anywhere, from quiet cafes to loud bars. Give it a try.

TIP NO. 17 SHOW CLEAR ROMANTIC INTEREST

After you open in an indirect way, within a minute or two, start to pepper the conversation with a flirty comment or two, such as  “Wow, you have a sexy laugh. Anyway . . .” 
or “What do you do, when you’re not making handsome 
men flirt with you?” 


TIP NO. 18: SHE’S TALKING TO YOU . . . NOW WHAT?  

It’s simple: Keep the conversation about you and her. 

Now, if you used an indirect opener, you can talk for a bit about the icebreaker topic—say, the book she’s reading or boots she’s wearing. Then change subjects. A simple way to do that is to introduce yourself and shake hands. This lets you bridge to the next topic.

TIP NO. 19: ANSWER YOUR OWN QUESTIONS

Beware of “interview mode,” where you pummel a woman with questions, and offer little about yourself.

A simple way to fix this is to answer some of your own question, especially if she’s not asking you many questions.

You: “What do you do?”

Her: “I’m a nurse at XYZ hospital.”

You, answering your own question: “Oh, cool. I’m a software engineer at XYZ company…”

It’s totally normal to ask questions. It shows interest. Just beware of interview mode.

TIP NO. 20: HOW TO APPROACH WOMEN? GET COACHING!

If you want to get great at approaching women, here’s one more tip: Book a free call with me right now. Simply grab a time that works for you, and you and I can hop on the phone. Just go to this link:

www.datingtransformation.com/contact

If we’re a good fit to work together, I will personally teach you my latest, greatest tips on how to approach women, so that you can attract an amazing girlfriend.

Book a free call today! Click here.

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Connell Barrett Dating coach for men

I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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