Ok, if you told 17-year-old Peter guys would be coming to him for dating advice, he would have called you crazy, then asked if you wanted to see a magic trick.

Now I’ve come to accept that I am basically a Will Smith Hitch / Ryan Gosling Crazy Stupid Love hybrid, marinated in soy sauce.

One of the questions that always comes up:

“How do I ask a girl out in a chill way? I don’t want to look desperate.”

Look, I know I’m going to sound old here, but why are the young ones so worried about seeming chill these days?

You know what’s really chill?

Getting what you want and not being stressed out from all the confusion cause nobody can communicate what they actually want.

Working with guys 1:1 on their style has taught me a lot of things. Like translating what guys mean when they say things like:

“I hate shopping.”
(Translation: I don’t know what I’m doing.)

Or “I just like to dress comfortably.”
(Translation: I wear baggy clothes because I don’t want people to think I look gay.)

So when a guy says his friends are telling him to “be chill,” what he’s really saying is “I don’t want to put myself out there and get rejected.”

Look, I get it.

I’m not going to sugar coat it, rejection isn’t fun, but there is a solution…

Don’t Fake it Til You Make It, Do it Til You Make It

One of the dumbest pieces advice I see all the time is “Just be confident! Fake it til you make it!”

That’s not how confidence works.

Here’s the BIG secret: you get better and more confident at handling potential rejection the more you ask a girl out.

Notice I said potentially. Guess what…you’re not going to get rejected every time. There’s a likely chance she’s going to say yes!

It’s like driving a car.

The more you’re on the road and haven’t crashed and died in a fiery inferno, the more confident you get at driving.

Before you know it, you’re driving while drinking coffee and Snapchatting a conversation with your friend in the passenger seat.

How to Become Confident Authentically

A few days ago I went to a lunch with legendary marketer Jay Abraham and got to ask him one question. Here’s what I asked:

“How does someone reach places they can’t even dream of?”

For me, I was asking about growing my business. But this problem applies to guys who aren’t used to asking women out.

It was Ramit Sethi, my business mentor who was also at lunch, that gave me the great advice.

Break it down into smaller milestones that you can imagine.

I can’t imagine making $1 million? Ok.

Can I see $500k? No?

Ok, what about $200k? $150k?

Hit that milestone goal first, then look for the next milestone.

Let’s go back to the driving analogy. If you’re 15 and about to start drivers ed, the thought of taking a road trip is downright frightening.

So you start with the end goal, then work your way backward.

Let’s break that down.

Doing a road trip across the U.S. -> Driving to the next state over alone -> Driving across your state -> Driving a few cities over -> Driving on the freeway -> Driving across town -> Driving around the parking lot

When it comes to asking women out on dates, here’s how that looks:

Asking a woman you like out on a date -> Talking and flirting with an attractive woman (without losing your shit) -> Complimenting an attractive woman -> Complimenting a woman you’re not attracted to/stranger -> Complimenting a stranger.

You can’t fake confidence into existence, you build it up.

You start from the bottom and work your way to the top. Start by giving a stranger, male or female, an authentic compliment. Make it low stakes – the guy making your coffee. The person in line in front of you.

It might be their haircut. A tattoo. Maybe you’ve noticed they’ve been writing in their journal at the coffee shop and they have amazing penmanship.

Tell them.

If a conversation sparks up, chat for a bit. But don’t make it the goal.

The goal here is just to start talking to people without an end in mind.

Then work your way up to conversations, then to conversations with women you find attractive, then to asking a woman out.

With each milestone you hit, you get more comfortable and confident. Go from driving around a parking lot to making a road trip across the country.

(Btw, one of my favorite people to compliment and start conversations with, and even flirt, are old women. They don’t give a fuck and will TOTALLY flirt and charm you right back.)

Give Her The Option To Say No (And Don’t Be A Dick About It)

One thing a lot of men don’t realize is how different the dating experience is for women.

If you want a wake-up call, just ask your female friends who are on any dating app to show you their inbox. I’ll bet you $100 it looks MUCH different than anything you’ve ever experienced.

When it comes to finally asking a woman out on a date, there are a few extremely important things to remember.

  1. So many dudes are “chill” (afraid of rejection) that their ask isn’t clear. So they might say yes thinking it’s a friendly hang when the guy thinks it’s a date.
  2. Women are used to guys blowing up on them after a rejection.

The first one is what we’ve been talking about this whole post. So be clear with your ask. Don’t say hang out. Don’t say grab a drink. Use the word date.

The second point is extremely important.

This is one of the reasons why women will often give you a soft rejection, like saying they’re really busy right now, or tell you they want to be friends and ghost you because that’s safe.

This is one case where it pays to show how chill you are, just not in the way you think.

You want to be clear about what you want but chill with the possible outcome.

Give her the ability to say no to your offer, and let her know it’s totally cool.

And actually be cool about it whether she says yes or no!

Be chill.

Your ask might look something like this:

“Hey! It was great meeting you at Justin’s party yesterday. I can’t believe we were the only ones eating the guacamole. Anyways, I’m taking a coffee break from work and wanted to know if I could take you on a proper date sometime? (I know some secret places with even better guacamole.) It’s TOTALLY cool if you say no, I had a great time chatting with you either way.”

And if she says no, be chill.

And if she says yes, be chill. (But feel free to freak the fuck out internally)

And here’s the crazy part, the fact that you said it’s cool if she says no signals that you’re an emotionally stable dude. Which will increase the likelihood she says yes.

Just remember, you have to mean it. And you get better at that the more you do it.

Step Up Your First Date Style

One of my favorite scenes in Hitch is when Will Smith reminds his clients that the girl he’s going on a date with already said yes, so his job is not to mess it up.

When I hear horror stories from my female friends about guys showing up to the date wearing fleece Patagonia pullovers (true story), I want to kill myself.

Dudes can bitch and moan all they want about being judged for their looks, but guess what? You’re probably on this date because you thought she was attractive too, so it’s actually a sign of respect to bring your A game and make sure your style is on point.

Luckily, I got your back. I’ve written two articles to help make sure you look really good on that date.

Check them out below
“I Asked 101 Women What a Man Should Wear On a First Date”
“A Beautiful Woman Lets You Know How to Dress (and What to Do) On a First Date“

Set Yourself Up For Long-Term Success

One of the most game-changing things you can do to improve your dating is setting yourself up for long-term success.

I call this the “ROI of Self-Improvement” rule.

The quicker the fix, the smaller impact.

Getting a new haircut and shave? Quick and easy. Small impact on your attractiveness.

Losing 50lbs? More challenging and longer fix. HUGE impact on your attractiveness.

A great example is my client Bill, who starting working with me after losing an astonishing 185lbs!

Going beyond his weight loss, Bill invested in working with me to craft his style. His progress from when we first started to now is like night and day. (Check out this hilarious clip of him sharing how he’s giving his friend’s style advice now)

If you want to make a huge impact on your confidence, your style, and your dating game, book a free consultation call to talk about becoming one of my private 1-on-1 styling clients.

I only have two slots a month for clients, so book a call if you don’t want to end up with a slot months from now.

Be Chill. Be Clear. And dress well. You’ll be good.

Can’t make it to NYC to work with me? I have another option for you

I know a lot of you guys aren’t in the NYC area, or can’t fly out here to work with me.

Totally understand. If you want to take your style to the next level and work with me remotely, I have an awesome online private styling service.

It’s based on the exact framework my in-person clients get. You and I will work together for a season to transform your style, and the best part is you don’t have to leave your city (or country!).

This is my most popular styling package, and I’ve already booked half my clients for this season. If you’re interested in hearing more, let’s jump on a short call.

peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here