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5 Tips for Feeling Confident Approaching Men in Real Life

By Lisa Copeland July 14, 2022 Dating

Let’s say you’re out and about, and you see an attractive man you’d like to meet. You want to go up and talk to him, but you haven’t flirted in years and putting yourself in a situation where you might get rejected feels way too scary.

So, you decide to keep moving, and you end up letting an opportunity pass by for meeting someone you wanted to get to know. Something you might not understand about men is, they are just as scared to approach you for the same reason you fear going up to them.

Well, what do you do?

You need to encourage men in a way that lets them know you’re interested so they feel safe talking to you. The 5 tips I want to share with you will help you feel more confident when these situations for meeting come up for you. 

Smile and Make Eye Contact

Smile at a man you’re attracted to and make eye contact with him for five seconds. Yes, five full seconds…. It will seem like an eternity, but it’s a signal to him that you’re interested.

If you’re sitting with a friend at an upscale bar and you see a man across the room, look up at him and smile. Then turn back to your friend. About 10 seconds later, look at him again. You’ve just signaled you’re interested, and he can approach if he wants to get to know you.

Ask Well Thought Out Questions

Get a man’s attention by asking a question. Remember, men are wired to help women, so your questions want to trigger his hero response.

Here are some examples of questions you can ask to get the dialogue going between the two of you.

Scenario #1: At Happy Hour

You’re at a happy hour with a friend. A man sits next to you and orders red wine. Tell him you’ve wanted to try red wine and ask him what he’d recommend. This situation gives him a chance to share his knowledge with you.

Make sure to thank him and tell him how much you appreciate the info and watch his chest puff up because he’s proud he could help you.

Scenario #2: The Coffee Shop

You’re at a coffee shop. Ask if the chair next to a nice-looking man is taken. Or if you’re in line, ask what his favorite coffee is or talk about the weather. These are ice breakers that can get a conversation going.

Scenario #3: The Dog Park

You’re at a dog park. Ask a man you’d like to get to know about his dog’s veterinarian and if he’d recommend him or her for your puppy.

Listen to a Man’s Words

Make a habit of listening to men. Sometimes they give you hints about being interested in you. The problem is, men and women speak a slightly different language that neither always gets. Here’s what I mean:

Heidi was sitting at a bar having dinner with her friend. The two of them struck up a conversation with a good-looking man who sat down next to them. Her friend asked him the question, “What’s in that salad? It looks really good,” and the conversation between the three of them took off.

When her friend left, Heidi and this attractive man from out of town continued talking. Over and over he shared with her that he wasn’t locked into where he lived and that he’d seriously dated women from cities other than the one he lived in.

Heidi totally missed his male language hint for “Are you interested in dating me even though I live out of town?” ultimately losing out on an opportunity to date a man she was quite attracted to.

Drop an Item to Strike a Conversation

To this day, I Love Lucy™ remains a favorite television show. In one episode, Lucy, wearing a wig, was pretending to be another woman. She wanted to see if Ricky would flirt with her. Back in the 1950s, a woman would drop her handkerchief in front of a man to let him know she was interested in him.

So, in this episode, Lucy drops her handkerchief and says to Ricky, “Pardon me,” fully expecting him to pick it up for her. Both understood this was a signal she was interested and, if the attraction was mutual, he could start a conversation with her.

You can do the same thing with men today. Instead of using a handkerchief, try dropping your phone if it won’t shatter or a folder or package you might be carrying. Who knows what it might lead to!

Communicate Your Interest

Your job is to let a man know you’re interested in having him approach you. His job is to ask you out if he’s interested in you. If he’s not, it doesn’t mean he’s personally rejecting you. He might be married, have a girlfriend, or you might not be his type.

Just move on… There are plenty of other men out there. Chalk the experience up as an opportunity to practice your flirting skills.

How often do you meet interesting men in real life? How do you communicate your interest in them? Have your actions produced any fruit? Please share your stories and tips in the comments below!

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The Author

Lisa Copeland is a leading internationally recognized Love Coach and Dating Expert for women over 50 inspiring and teaching them how to feel confident, empowered and joyful dating. You can get a free copy of her eBook “The 5 Little Known Secrets to Finding a Quality Man” at

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