Asking a Guy Out Can Be Fun with These 5 Tips!

For as long as I have been interested in women, I dreamed that just one would walk up and ask me out, “Gregg, you handsome devil, wanna go out with me?”

56 years later – I’m still waiting!

OK maybe a few did but I sure as heck can’t remember when and, if a woman did, she probably was a hunch back with a tail.

Men are rooting for you to ask them out.

My point being, is to ask a man out! We want you to. Men will root for you. We are more afraid than you are – that I can guarantee.

Add the #Metoo movement and now we think you will have us arrested if we even flirt with you.

It takes some degree of confidence in yourself to ask a guy out. I get that. That’s why my website for women has a slogan across the header that says, Build Yourself and He Will Come!

If you see yourself cringing at these five ways on how to ask a guy out then you need to hit the confidence page and get some.

So what are the best ways to ask a guy out? The key is to put yourself in the position to ask a guy out so you can ask the question more comfortably.

The actual question is often the easy part. It takes confidence, but it’s easy.

How to ask a guy out:

#1: Pick something on your bucket list and go for it!

Let’s make asking a guy out easy by setting the stage.

Brainstorm 50 ideas (hobbies/passions/new adventures) narrow to 10. Pick 1 or 2, sign up and go! The goal here is to get exposure and join with guys that you have things in common with. This takes the pressure off from meeting a man while you are having fun!

Don’t join yoga unless you are asking women out.

After a couple of white water trips, for example, it’s a hell of a lot easier to look at the guy who paddled you down the river and say, “Jim, you saved my life from those class 5 rapids, let me take you out for a cocktail Saturday!”

Notice you are telling him and not really asking. This shows confidence!

If he says yes, then you are golden, if he says no, then pat yourself on your shoulder and paddle away.

#2: Use a corny pickup line

Guess what? Pick up lines suck if you’re a guy using them on a woman.

But, they work the bomb directed to guys from women! Why? Because we are a bunch of barely grown up third graders and crappy pickup lines were a part of our heritage. I still laugh at them with my friends.

So when you use them towards a man you are tickling his funny bone and that’s a good thing!

Here are a few:

Do you have a sunburn, or are you always this hot?

I seem to have lost my phone number. Can I have yours?

Are you Australian? Because you meet all of my koala-fications.

I’m not drunk, I’m just intoxicated by YOU!

OK I cheated and stole these here – https://www.pickuplinesgalore.com/cheesy.html

Your goal is to get him laughing. You don’t even need to be smooth. If you mess up the punch line that’s even better!

How to Ask a Guy Out Tip #3: Study comedy and use it towards strangers

how to ask out a guy

Getting him to laugh makes it easy to ask him out!

The best way to get to know someone is to make them laugh. I was gifted with funniness, (is that a word?) so I was lucky, but some women have nothing.

Change this by going to comedy shows and listening to comedians. Steal a few lines. Watch their deliveries. Practice on your friends. It works.

I have ten or so lines that I still use today and they are the perfect way break the ice so you can ask a guy out.

For example, when I go to my place in Delray Beach, I always eat at the same sushi bar. There are a lot of other people sitting next to me. I poke my raw tuna with my chopsticks and say in a loud voice, “A skilled veterinarian could bring this tuna back to life”

Is it stupid? Yes. Is it funny? Hell yeah! Everyone laughs. A steak restaurant works too.

The sillier the better when it comes to lines. I was with a group of women in LA and one wanted to meet this guy. I told her to grab the guys little drink umbrella and put it in her hair, smile, say her friends challenged her to do it, and offer to buy him another drink.

He laughed his ass off and bought her a drink. It works.

I swear the more you act like a little kid, the more a man is drawn to you. If he’s not, then you never wanted to meet him in the first place!

How to Ask a Guy Out Tip #4: Walk up, hand him your phone number and leave

This tip comes with options!

Really? Yep. How much easier does it get? It even meets my act like a little kid requirement.

This tactic comes with many variations which is nice too:

  • You could strut back to your friends and see if he approaches
  • Tease him and say, “This is your lucky day my friend – I never come on the market” and leave.
  • You could say this line, grab his little umbrella and stick it in your hair and then walk back over to your friends!

The skies the limit.

#5: Have your friend approach him

Have your friends approach him for you!

I do this with my guy friends and it works great! Especially with John, my shy buddy. Have your friend walk over to a guy you like, grab his hand, and say, “my friend wants to meet you, she’s a bit shy so I am taking you to her.”

Perfect! Start talking, get to know each other and then ask him out like this:

Jim, we are all going to the wine tasting next Friday at the Seaport area in Boston. Are you busy? Grab some of your friends or come as my date and let’s savor some grapes! Here’s my number – bye!”

Then make a smooth exit. Now go somewhere else – rinse and repeat.

Like anything, it’s a numbers game. The more exposure you get the more potential dates you will get and the less you will care about any one of them.

Also, the more guys you talk to the more relaxed you will be asking guys out. This is called desensitization and its one of your tools in my confidence course book, Comfortable in Your Own Shoes.

Get it for the price of a cup of coffee – it may change your life.

How to get a guy to ask you out | 5 Sneaky Ways

So we covered how to ask a guy out but what if you are too shy? Are there ways to get the guy to ask you out instead?

There sure are!

Tip #1: Put your friend to work

Arrange for your potential suitor to join you and your friends (and his) for a get together. No pressure just request to get everyone together for the wine tasting on Friday night.

Then, when you are sipping wine together, have your extroverted friend walk up and say, “you two would make a great couple – Jim, ask her out will you?”

This might create an embarrassing moment but who cares! You didn’t create it.  And he just might ask you out on the spot or at least think about it in the future.

How to Get a Guy to Ask You Out Tip #2: Ask him for a favor

Ask him for a ride and get one on one time!

Guys love to fix things and help women. It makes us feel good to get our egos stroked. Look for a situation where you can use this to your advantage. If he has a truck you could ask him to move some furniture for you.


Ask him to give you a ride somewhere that you know he is headed. This puts you in a one on one situation that could make him see you as a potential couple. Then, you can thank him by inviting him to join you for lunch or a cup of coffee.

Tip #3: Flirt using body language

Few women know how to effectively use body language. In my book Night Moves, I cover this in detail. You can get a guy to ask you out by giving him a huge dose of attention. Smile. Lock eyes with him for longer than you would normally.

Compliment him in front of his friends and yours. This will naturally draw him to you. Touch him too, by putting your hand on his shoulder.

One key tip: Vary your attention towards him based on his responses. Don’t be too aggressive or he will be turned off. Go “in and out” with your compliments, touching and smiles. This will pique his curiosity! He won’t know if you like him or you don’t and that’s what you want!

Now, he will only concentrate on you and not other women. Clever as a fox!

Tip #4: Find his passion and get him to talk about it

Find his passion and talk to him about it!

If he loves surfing then ask him about it. Even better, learn about it and try it! When you share a guy’s passion, he starts to equate you with his love for his passion – in other words, you increase the chances of him wanting you in his life!

Now, when he mentions going surfing, you say “bring me, bring me!” as only a woman can say in her wonderful je ne sais quoi way.


If you start asking me about writing books for women – you can damn well bet that I will give you my undivided attention.

How to Get a Guy to Ask You Out Tip #5: Ask him what he is doing this weekend – then tell a white lie!

This works well. Ask the guy what his plans are for the holiday weekend. When he tells you, tell him that you and your friend are going there too!

OK, you’re not but now you are. Then tell your friend that she is going whether she likes it or not and then buy her lunch.

When he sees you, this puts you in a great situation for him to ask you out in the future. It’s almost like you are having a first date without ever asking him out.

How to Ask  Guy Out Conclusion | Do not fear failure!

Never fear failure!

Do you know who fails more than anyone?

Yours truly!

I fail because I take risks to find out what works. I live outside my comfort zone. You see, you can’t succeed if you don’t fail. Do you think Thomas Edison got the light-bulb right on the first try? Nope. It took him over 1000 tries!

Look at failure as the road to success, not as a judgement on you.

The real failures are the ones that complain how terrible their lives are and do nothing about it.

You are not that person! You are now the women who is proactive asking guys out!

So there you have it, my 5 sure-fire ways on How to Ask a Guy Out and my 5 ways on How to Get a Guy to Ask You Out.

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