A 10-Step Guide To Expertly Flirting With A Cute Guy

Show them the confident woman you are.

Woman follows guide to learn how to flirt with any man of any age. DAPA Images, SrdjanPav, StockLite, | Canva

Why is mastering the skill of flirting a good thing if you're trying to get a date? The answer: Because men like confident women. They like women who are self-assured and know what they want. Flirting isn't easy but the rewards are great. The act of flirting can dramatically increase your chances of getting asked out on a date. At the very least, if the guy you've flirted with isn't available, he'll still find you entertaining and remember you in the future. Here are 10 steps to becoming an expert flirt.


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Here is a 10-step guide to expertly flirting with a cute guy:

1. Say hello to a stranger every day

This may seem easy but it can be quite intimidating. The exercise of smiling, making eye contact, and greeting a total stranger may seem completely foreign to someone who hasn't done this in the past. Ever since learning about "Stranger Danger" in grade school, we were taught not to make contact with strangers. The simple act of saying hello to new people will brighten your day and those you greet.

2. Give a sincere compliment

Compliment a co-worker, friend, or stranger by saying something unexpected and nice. If you aren't able to leave your home, try saying a positive statement to someone on the phone. Watch and listen to the reaction you receive from that person.


3. Introduce yourself to an unknown person

This can be anyone unfamiliar to you: your server at a restaurant, your grocery cashier, or a bus driver. Make sure you smile and look the person right in the eye as you say, "Hi, my name is X. What's yours?" 

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4. Strike up a conversation

Go to a bar, restaurant, gym, or any social gathering place and chat with a stranger. Talk to someone sitting at a coffee shop or strike up a conversation with a girl in a hair salon. The more comfortable you are with this step, the easier it is to start up a conversation with a man you are interested in getting to know.


5. Feel comfortable to approach someone

You are now ready to approach someone you'd like to potentially date. This can take place anywhere: a bar, your favorite grocery store, the dog park, or the car wash. Be ready at all times so you don't kick yourself later about letting the guy get away. Once you've found your target, make friendly eye contact and give him a big smile. 

6. Make your move

Walk up to that person and say something relevant about him or your surroundings. You can comment on the weather. You can discuss something on TV. You can even pretend to be interested in the sports team on his hat. Bring up any subject that will get his attention. Make sure to use great eye contact and give him your full attention. Do not look at anyone else or pick up your cell phone. If he indicates disinterest by turning away or grunting a one-word answer, move on to the next guy. I once walked up to a group of guys in a club and boldly asked, "Which one of you guys want to dance with me?" I ended up dating the brave lad for over a year.

7. Keep the conversation light and flowing

Tell a joke and respond to his attempts at humor. Ask a question; then actually listen. This may seem obvious but everyone likes to talk about his/herself or voice an opinion. If you listen intently and respond with a nod or smile, he'll feel special. If he shows you pictures of his kids or dog, you know you've captivated his interest. Those are a man's treasures and he wouldn't bother bringing them out if he didn't care to impress you.

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8. Make subtle body contact

Touch his arm, shoulder, or hand. If you get bold, you can brush your leg up against his. This tiny gesture will indicate you're interested in him as more than a friend. This will help keep you out of "The Friend Zone." If he returns the gesture, you're on the right path. 

A 10-Step Guide To Flirting With A Man Of Any Age Pexels / cottonbro studio

9. Keep the conversation short and sweet

You want him to look forward to your next meeting. Find out if he's in a relationship. If he's available, tell him you need to leave but would love to see him again. I once flirted with a guy at a bar who was waiting for his date to show up. I left him my card, and offhandedly said, "If your date doesn't work out, give me a call." He called me the next morning and we went out that evening. He said he was impressed with my self-confidence and couldn't wait to see me again.


10. Give him a sweet goodbye

Get up and shake his hand, give him a quick hug, or, if you're comfortable, a light kiss on the cheek. Tell him how happy you are to have met him and say goodbye. The art of flirting is not just about batting your eyelashes and tossing your hair. It's a skill that lets a man of any age know you're confident and he won't be rejected if he asks you out. 

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KarenLee Poter, MSW, is the host of the KarenLee Poter Show on dating, love, and everything in between, as well as the author of A Cougar's Guide To Getting Back Out There.