10 Ways To Charm Even The Most Intimidating Guy

Follow these strategies to entrance any man you set your sights on.

Woman charming a rather intimidating guy on bench Dikushin Dmitry | Shutterstock
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Some women find it hard to muster enough courage to talk to a guy they like — especially if he's super attractive or otherwise seems out of reach. They may even worry that making the first move or appearing interested will annoy a high-status guy. Fortunately, most guys are charmed by women who seem excited to meet them. 

To start charming him, remind yourself your crush has flaws and insecurities just like you. Bring him back down to earth in your mind, and it will be a lot easier to initiate a conversation. Then, follow these ten steps. 

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RELATED: Why You Need To Stop Overthinking And Make The First Move

How to charm even the most intimidating guys

1. Check his "crushability"

Before you initiate anything, you need to be sure this guy is worthy of your attraction.

Sometimes, you can be attracted to a guy and approach him, but after ten minutes in his presence, you realize he utterly repulses you. If you are not in a position to ask someone about the guy, all you have to do is observe.

How is he behaving around his friends? How is he treating other people, for instance, the waiters? Is he nice or is he a jerk? Be sure he is considerate to others before you make any move, as shown in a study of empathy and relational competence published in the Journal of Personality and Social Psychology.

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Confident man looks invitingly at tyou Olga Kri via Shutterstock

2. Figure out the best time to approach

When it comes to approaching a guy, timing is everything. Not so much on your side, but on his side. The longer you leave it, the more likely you are to talk yourself out of it.

3. Stop making excuses

Some of the excuses you may tell yourself include:

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  • His friends: It might be a bit intimidating to approach him while his buddies surround him, but it also shows great confidence. He will enjoy it.
  • The place: Sometimes, you think there are social rules that include not approaching someone at certain places, like the train, library, church, and wherever else. These only really exist in our minds. Most people there simply don’t care what you do, as long as you're not hurting someone else. They will more likely be cheering you on.
  • The time: Is it too early to meet the man of your dreams? Oh, I guess you will never meet him. Come on listen to yourself here, this one is silly!

As you can see, there isn't any good enough excuse, but your brain will try to stop you because it thinks it’s protecting you. A study from the Journal of Family Issues shows how this is an old reaction we have some people never overcome.

How do you approach a guy confidently when you're not actually confident?

First, make eye contact and smile at your crush. Pay attention to his response. Does he smile back? If you feel that this has gone well, it is time for the approach.

Studies conducted by the Journal of Social and Personal Relationships support that all a man needs to open up to you is to know that you are interested in him. If you appear pleasant and approachable, a man who likes you will be more open to having a conversation with you.

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One of the biggest problems women face when figuring out how to get the guy is striking up a conversation and the awkward silence. It is not enough to initiate a conversation. You need to ensure it is the right conversation.

RELATED: How Every Great Guy Wishes You'd Communicate With Them

4. Ask for his help

Bringing out a guy’s protective instinct will make him feel more connected to you. Depend on the guy for something. Ask him to carry a few books for you because they are too heavy or to walk you down the street because it is dark. You can even ask him for directions or time, as supported by study of motivations and preferences in romantic relationships published by Frontiers in Psychology.

Men love to feel needed and helpful. So, find a reason to need his assistance. After he has helped you, thank him for his help and offer to buy him coffee to express your appreciation.

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Couple smile as she hold him tight PeopleImages.com - Yuri A via Shutterstock

5. Compliment him

Research from the Western Journal of Communication explores how compliments help bring two people closer. No one is unreceptive to a sincere compliment. If you genuinely feel that there is something worth complimenting about a guy, tell him about it.

Be specific: tell him how cute his shoes are, or how well he has put his entire look together. Tell him that he has a gorgeous smile or that his dimples give him a boyish charm that you find adorable.

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If he finds you equally attractive, he may respond with a few compliments of his own, and you will have broken the ice.

6. Tease him

To spice up the conversation, tease the guy a bit, fun and laughter are bonding, as a study in the Journal of Positive Psychology confirms. You can tease him by pointing out a cheesy line he uses during your conversation, "Oh! Did you think you won me over?"

Or, you could look at the clean-shaven head and tell him, "You would look great with a huge blue Mohawk. It would bring out the gorgeous blue in your eyes."

Suggesting an extreme makeover for a guy you have just met is excellent for a feeling of instant connectedness. It is also a way of complimenting him without being too serious. It can work with clothes too. Suggest a pair of tight white flairs and see him smile.

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You can also result in a competitive tease. Pick something he says he is good at and challenge him to it. The good thing is you don’t even have to be good at it.

If you beat him, he will be impressed and if you lose he will bask in the glory of comforting you. "So you think you are good at pool? Let’s see how good you think you are after a game with me!"

7. Move the conversation after the first two minutes

If you have been talking for a while, it can be a good idea to move. Try one of these:

  • Let’s go and get a drink.
  • You have to meet my friend.
  • You have to see this.

These can get your guy to move so you can have more of an intimate conversation.

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RELATED: The Unexpected Secrets I Learned Working As A Love Coach In A World Of Lonely Men

8. Ask him questions

A study from East Tennessee State University shows the importance of getting him to speak about himself. Start with general questions and only ask personal ones as the conversation progresses.

If you are attending a function, ask him how he knows the host or why he is there. You can also ask him random questions like, "What’s your Myers Briggs Type indicator score?"

As you warm up to each other, you can go off the beaten path and ask questions that are a little less ordinary:

  • "What is the craziest thing you have ever done?"
  • "If you could fly anywhere right now, where would you go and why?"

Finally, if everything is progressing well, you can get personal:

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  • "How is someone like you single?"This is a great question to find out if he is single while still flirting with him.
  • "What’s your idea of perfect date?" This question gets him to talk about himself and think about what a date with you would be like.
  • "What kind of a relationship are you looking for?" This is an excellent question because it lets you know where his head is at.
  • "Do you like it when girls make the first move?" This is a perfect question that helps you find out if it is ok to ask him out or wait for him to make a move.

9. Find common ground

As you listen to the guy, take the opportunity to pick and talk about common interests. The more he feels you have things in common, the more easily the conversation will move forward, as demonstrated in research published by the Archives of Sexual Behavior.

Remember the guy’s thrill is in learning about you. After you have made contact with him, let him work his way into your life.

Do not prolong the conversation. Be coy and shy when saying goodbye to make it memorable. Also, ensure to take your leave just before things get awkward or boring. Leave him wishing that he spent more time with you.

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Let him know you enjoyed spending time with him and you look forward to seeing him some other time.

They look at each other happily over a menu Karelnoppe via Shutterstock

10. Tell him you can't wait to see him again

Approaching men first is a simple-to-understand yet hard-to-do concept for most women when it’s first introduced. But here’s the thing, not only does it help you meet more men, but it also gives you an ability some women don’t have, which translates into meeting men they will never meet.

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Approaching can be very hard at first and it might take a while to "get it", but when you do, you'll feel in control of your dating life like you never had before.

It’s not easy, but it’s worth it.

RELATED: My Partner Wouldn't Commit — The Question I Asked To Get What I Want

Randy Skilton is a relationship coach with an Advanced Diploma in Social Science. His work has appeared on Psych Central, Lifehack, and Marriage.com where he educates others on enhancing the quality of their relationships.