How To Ask A Guy Out - Without Embarrassing Yourself

By: Carlos Cavallo

If you've ever been confused about how to ask a guy out, we're going to answer that here for you. AND I'm going to show you some things you might never have thought of when it comes to making him say YES to you.

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Why is this all so complicated?

We live in some really interesting times - where men and women are confused about how romance works. In poll after poll, I find the same thing: Both men and women are really confused about what the "rules" are for asking someone out.

In most of the recent surveys and studies, the majority of women feel - on some level - that asking a guy out is a bit too forward. There's an implied feeling of "I must be slutty if I show my interest in a guy!"

Which we know isn't true.

BUT - we do believe is true - in a weird primitive part of our brains.

09 How To Ask A Guy Out   Without Embarrassing Yourself

So if you're at all like the women in most age groups - and that means ALL age groups - you want to know how to ask a guy out. And the SAFEST way to ask a guy out. It gets even more complicated if you're not sure how single he is.

One of the first questions I hear about asking a guy out is:

WHY should I ask a guy out?

After all, most women don't really want to ask men on a date - no matter how much the popular culture tells you its okay.

There are lots of reasons women don't want to ask guys out:

  • It's flattering when a guy asks you out...
  • "It's a man's job to initiate!"
  • "I want to know he's got the balls to do it - otherwise, how do I know he'll be able to keep me safe?"
  • "As a woman, I want to be chased!" She wants to feel desired...
  • How would you even know if he really found you attractive if you ask him out? He could just be going along to be nice...

And then you've got the magazines, movies, and web sites that tell you that you NEED to ask guys out if you want to be equals and promote feminism. Sorry, but I'm not going to go there with you.

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I was lucky - I had a dad that understood that guys need to have their dads show them how to get this courage up. My dad would put a 5 dollar bill (hey that was a lot to a young man back when I was growing up) up on our refrigerator - and he told me it was mine if I would go talk to Julie - the girl I liked. He knew that money was a great motivator for me.

Eventually, I did talk to Julie. I called her up on the phone and invited her to dinner. Her mom came over with her and it was really a cute dinner at home.

I was about 8 years old at the time. But my parent's recognized that I needed to develop the courage to do this, and to experience the reward of having her say yes. Now, nothing ever became of that relationship with Julie. I didn't wind up going to high school and college with her and becoming sweethearts.

BUT - it was a big deal to me as a young boy of 8. Not every guy got this kind of "training" or encouragement from their mom & dad.

10 How To Ask A Guy Out   Without Embarrassing Yourself

BUT there are some reasons why you - as a woman - might want to ask him out instead of waiting on him to do it.

Let me show you a few:

Why You Want To Ask Him Out: He's Chicken...

Yup, there are a ton of guys out there that are just plain scared to death of asking a woman out. If you have ever tried to ask a guy out, you probably sympathize! It's not easy.

There is a whole generation of men out there that have never really had to prove their manly status this way - or they just learned some weak and wimpy ways of asking women out.

Then there's the older guys in their 40s, 50s and up. A ton of these guys grew up without dads to show them the ropes on this. They have no clue how to ask a woman out because they were never taught.

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Chicken or shy guy?

I didn't feel comfortable approaching women until I was in my LATE 30s! And I had a dad that prompted and pushed me into being more outgoing.

So you could be waiting for quite some time before he decides to man-up and take a chance on you. If he EVER does.

This is why taking a chance to ask him out is going to work out better for you. You'll be casting a wider net, and you'll probably get at least twice the dates the other "good girls" get who are too scared to take a chance.

Why YOU Need To Know How To Ask Him Out: He's Intimidated AF...

If there's one thing that will shut down the bravest of souls, it's a guy thinking that he's out of his league with a woman. I've seen 6 foot 7 inch football players get tongue-tied and weak-in-the-knees when they're confronted with a beautiful woman.

And he might never get around to asking you out simply because he's already decided he's not worthy of you.

Yes, it sounds crazy, but it's a very common experience for a man. There was a study that showed if a person feels they aren't "hot" enough for you, they simply won't even try to get you out on a date.

16 How To Ask A Guy Out   Without Embarrassing Yourself

Ironically, this is also because a rejection from someone we consider higher status than us hurts us much much more.

So if he's feeling intimidated, that's mostly him. But you can help him move forward by busting a small move on him. Show him you're just an ordinary gal, and that you're easy to be with.

Once he feels you're on his level, he'll probably take the first step and ask you out. He'll lose the intimidation and pursue you.

Why You Want To Make The First Move: He's Scared AF...

Guys are in a weird place right now. Most men are still leery of talking to women after the whole "#metoo" movement. Not because they've done ANYTHING wrong - but because they think they might be viewed as some kind of predator.

No matter that they're not doing anything illegal or remotely bad. But to a guy who has been watching the news, or has been on any news sites in the last couple years, he's probably pretty hesitant to take the first step. He might need you to ask him out first.

He might think you're already dating someone. Or that he doesn't measure up.

He might just not know HOW to do it himself. And if you don't find some method of enabling you two to get together, you might spend the rest of your life wondering if you missed your chance with your soulmate.

A little cautious flirting can make the difference - and we'll talk about that coming up.

For now, let's take a look at some of easy tips you can use when you want to know how to ask a guy out...

HOW TO ASK A GUY OUT - TIP 1: Figure out if it's right...

You gotta know up front why you're doing it. To do this, you have to check in with your instincts.

I coach women all the time in the proper use of the "gut check." It's something that anyone can do, but so few actually do it.

best ways to ask guy out for date How To Ask A Guy Out   Without Embarrassing Yourself

You need to check in with your instincts before you do anything. Some guys might attract you, but you realize that he's not a good fit for you.

Why he might not be "right" for you:

  • He might be immature...
  • He might be a player...
  • He might be insecure...
  • He might be weak and indecisive...

And the only way you figure these things out is to look at him with clear eyes BEFORE you take any action. In a lot of situations you might find that you don't really want to ask him out, and you dodged a bullet.

Other times, you'll get a real sweet vibe from him and decide to go forward.

But in both situations, you get the advantage of checking him out first. Use that advantage up front!

HOW TO ASK A GUY OUT - TIP 2: Get Your Boots On...

You do have to eventually recognize that there are three possible reasons the guy you're interested in isn't doing anything about you:

REASON 1) He doesn't know you're interested and thinks you'd probably say no...

REASON 2) He's interested, but lacks the courage to do anything about it...

REASON 3) He's not interested...

So at some point you have have to just say "The heck with it" and just go for it. That's what I mean when I say for you to get your boots on.

23 How To Ask A Guy Out   Without Embarrassing Yourself

The worst situation is that he's not interested, and you're no worse off than you were before.

If he was interested in some way, then you just opened the door for him. At least now there's a shot at having a romance with him.

You just gotta find the guts within you to simply take a chance and ask him.

Sure, he might say no...

And he might also say YES.

You have to be willing to accept that the only way anything is going to happen is if you take that chance. You don't want to spend the rest of your life wondering "what if."

HOW TO ASK A GUY OUT - TIP 3: Do It The Easy Way...

If you can't get over your fear of him saying no, or not being interested, the best way to handle it is to get him out with a group. If you work with him, this should be fairly easy to do. Just get him out to happy hour or some group activity.

You can go to a group lunch to a local restaurant...

You can go to a local bar after work...

There are lots of possibilities if you don't know how to ask a guy out.

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Easy, fun, and relaxed...

I used to do the after-hours thing all the time when I was working in downtown San Francisco. I not only met a lot of great people from work this way (friends will bring friends from other departments), but I also met a lot of people at the places we went to because we were all in a social mood.

It's a huge win-win.

And this always opens the opportunity to do something one-on-one later on. Just use this opportunity to flirt and let him see that there's some interest from you.

I'll come back to this in a minute...

HOW TO ASK A GUY OUT - TIP 4: Get Some Java...

The best stand-by, low-risk, cool way to hang out is to just ask him to go get coffee with you. All you have to do is tell him you were heading out and thought it would be a good way to get to know him a little better.

It takes about 10 minutes to get coffee, if that's all you do. Which means that there's a low time investment.

If things look good, you can always sit down there and talk some more. If he seems like he's only interested platonically, then you can let it go without really risking much in the way of your self-esteem.

HOW TO ASK A GUY OUT - TIP 5: Flip The Tables...

One of the best ways to avoid risking your self-esteem when you want to know how to ask a guy out is to use some humor. You can ask him out in a funny "pickup artist" kind of way.

12 How To Ask A Guy Out   Without Embarrassing Yourself

This is a way of flipping the gender roles we're used to. You can pretend you're the player - and you're using your best "lines" on him.

For example, try this one on him: "Do you believe in love at first sight? Or should I walk past you again?"

OR: "If you were a phaser on Star Trek, you’d be set to stun!"

You get the idea, right?

You can even add a little "Austin Powers" swagger to it.

Guys will find this cute and endearing that you flipped the roles and felt comfortable enough to play the "pickup artist" on him.

And the humor can even take the sting out if he's not interested. You'll feel like you're not really risking your image in any way.

HOW TO ASK A GUY OUT - TIP 6: Send Him A Note...

This is where I'm going to endorse the different ways that different generations feel about using your phone to communicate:

  • If you're in your 20s or 30s, you'll have no problem using your phone to connect. You've probably been doing this since you were 8 years old.
  • If you're in your 40s or 50s, you'll think there's something a bit wimpy about doing it in text - buuuut you'll get over it and try anyway...
  • If you're in your 60s or 70s, you might think this is weird. But my aunt is in her 70s and she still texts me, so I know you can get hip to this...
reasons why women should ask men out for date How To Ask A Guy Out   Without Embarrassing Yourself

You have to start somewhere...

When it comes to the actual how to ask him out, you can simply use the tools we've got today to get things started - Use your phone.

Send him a quick email with an idea you'd like to share with him about an activity. This avoids the whole awkward asking him directly part. You can spend a few minutes - or days - composing just the right message.

Or send him a quick text with an idea for something to do together, if you've got his phone number. (And truthfully, it's not hard to get any guy's number. We'll give it to anyone.)

Passing notes worked in middle school, and they still work today. You don't even have to show up in person!

HOW TO ASK A GUY OUT - TIP 7: Send Him A Messenger...

This one is also a call back to being in middle school - just send a friend over to talk to him to see if there's any interest. You avoid any risk of rejection, and your friend gets to play matchmaker.

20 How To Ask A Guy Out   Without Embarrassing Yourself

It's always easier to send a third party who can "sell" you a little to him.

This works for someone you've known for a while, or even a guy you've got your eye on at a party. Just work out the arrangement in advance with your girlfriend to be "wing women" for each other.

HOW TO ASK A GUY OUT - TIP 8: Flirt Without Being Direct...

Look, the best way to ask a guy out on a date doesn't even involve asking him. It's more about pushing so many buttons in him that he HAS to do something about it if he's into you.

Just about the best way to get a guy to act on his desires is to make it perfectly clear that they are welcome.

In this day and age of sexual fear and politics that weird us all out, a guy just wants to know that he won't be sent to jail for acting on his desires.

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Wink, wink...

This is the ultimate test of a guy's interest:

If you flirt hard with him and he doesn't act on it, you'll know where you stand. If you flirt hard and he's responsive to you, you'll get a real good idea if he'd say yes or no to you.

Sun Tzu - the great ancient military philosopher once said:

"Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win."

Basically Sun Tzu is saying that you never need to jump in and risk anything. Instead, do what you can to win the "war in advance" by applying some strategy - and you will win.

In love and romance: You should be able to get a pretty clear idea how he'd respond to you asking him out BEFORE you ever have to do it!

You just have to know how to read a guy's signals. I'll tell you how to do that next...

HOW TO ASK A GUY OUT - TIP 9: Be Cool, and Roll The Bones...

One of my favorite bands has a song called "Roll The Bones." It's a great song about taking risks. And the song is about how we often look for all kinds of reasons and evidence to do something. But the funny part is that we're doing all this research just to avoid taking a risk.

We're stalling!

We're trying to be sure about stuff that you simply can't be sure about.

pros cons asking men out for a date How To Ask A Guy Out   Without Embarrassing Yourself

Take chances...

When it comes to another person's interest in you, you can never be sure that he's going to dig you. But I'd say there's a better than 50% chance he does like you.

Most men are plain clueless about women these days. That's why I spent over 16 years teaching guys how to man up and demonstrate that masculine confidence.

From my own experience, I can pretty much guarantee that no man would be offended or scream "harassment!" if you were to ask him out. It just ain't gonna happen.

And if you wait around, you could miss out on the guy who's The One for you.

So the risk isn't really about him as much as you fearing being rejected.

Or even FEELING rejected if you ask him out and he doesn't seem interested. And that's a perfectly valid concern you might have.

If you don't feel you could handle a "no" from him, or that it would drive you into a deep, dark depression - don't do it! Get to work on your feelings of worthiness so that you CAN handle it if he did.

Because - believe it or not - most men are running around DEATHLY afraid of a woman saying no to him. Which is why he doesn't do what you're considering doing - asking you out!

There's a way to avoid any risk when it comes to showing your interest in a guy - and that's knowing what he's saying with his body language and his signals. Every guy is sending you messages that you're probably missing.

The honest-to-gosh reality is that a woman needs to know how to read a man's signals.

Guys throw off signals all day long - and they tell you exactly what he's thinking and feeling - IF you know what to look for!

I pulled together a list of his signals into a short course you can go through RIGHT NOW.

Just go on over here for more...

PRODUCT Read His Signals How To Ask A Guy Out   Without Embarrassing Yourself



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