How to Approach a Guy You Like Without Looking Desperate or Weird

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I still remember the night I met my fiancé.

I was on a cruise ship, walking around by myself late at night. I saw a group of people, and (unbeknownst to me) was faced with one of the most important decisions of my life: was I going to go back to my room and go to sleep like a grandma or was I going to be brave and approach this person?

While this seems like a simple question with an A or B answer, the truth is…

It’s HARD for women to actually approach a group of people, let alone a guy they’re interested in talking to.

This is for a slew of unfortunate reasons.

It can be perceived as aggressive, weird, desperate, or even slutty. A friend of mine says she eyes good-looking guys all the time, yet she immediately stops herself from even thinking about approaching them. She thinks, “What am I going to say?” “Am I going to sound like the lamest person who ever lived?” “Is there something in my teeth?” “Am I a whore now?”

And so she lets the guy who might be a great date—which could turn into an amazing relationship—simply walk away without ever knowing what might’ve happened.

This is sad. It’s like watching the life you thought you were supposed to have casually drift by without a second glance.

But what would have been even sadder is if back on that cruise ship, I had decided to just go to sleep that fateful night. Instead, I met the love of my life by taking the taboo approach.

How to Be The Sexiest Woman Alive

You’d be amazed by how often attractive guys wonder why they don’t get approached by more women. Obviously, it’s for the reasons above but it also comes back to the belief that a guy doing all the work is just how we do things.

But it doesn’t have to be some aggressive, slutty move to approach that cute guy at the gym, and it shouldn’t be weird to talk to a guy at a bar. How else are you going to know if he’s interesting or not?

The analogy I like to think about is this: when a woman walks into Bloomingdale’s, she doesn’t stand back and look at all the gorgeous clothes and go: “I’ll just wait right here. Bat my eyelashes, flip my hair, and these lovely items will come right to me.”

What does she do instead?

She goes over to whatever draws her attention, and she inspects it carefully. She holds it in her hand, looks it over, feels the material.

Does she have outfits to wear it with? Are the shoes the right size? Are they comfortable? 

Only AFTER asking those questions does she give it a green light.

If not? It goes right back on the shelf and she goes on her merry way.

Now, what if our fictional Bloomingdale’s is a bar or event you’re going to tomorrow night where you could meet an incredible guy?

Today, I’m going to show you how to be the most confident woman in the room by making an effortless approach, dazzling him with conversation, and THEN deciding whether or not you want to take the goods home with you, so to speak.

(For the fitness side of how to be the sexiest woman alive, check out this article on that very topic.)

1. From “Does he like me?” to “Do I like HIM?”

Because dating can be so sensitive and intimate–I mean, our egos are on the line–we tend to turn into these puddles of insecure goo when it comes to thinking about approaching someone else.

What will he think? Does he like me? Am I pretty enough/cool enough/sexy enough? Is this that bad dream where I’m suddenly naked?

While this is normal, it’s also ass-backward.

INSTEAD, we’ve got to turn the tables: Do I like HIM? Do I like the way HE looks? Does he seem cool, smart, and interesting?

Because the reality is we get to CHOOSE who we want to approach and talk to, and we’re not at someone else’s whim to let them decide if we’re good enough. Remember, we have to approach those gorgeous shoes in a store to see if we actually like ‘em before we buy ‘em.

So the first thing to remember is that this isn’t about being liked–it’s about being open, but selective.

2. The Effortless, Non-Desperate Approach

For most people, approaching can feel like you’re climbing a mountain with no end in sight. Everyone wants people to just come to them, because then they don’t have to feel the anxiety and potential rejection that goes along with approaching a stranger.

But what if approaching was as easy as making eye contact, smiling, and then using the easiest pick-up line in the world?

Here’s what you do:

First, you make eyes and smile with whoever catches your fancy. Pay close attention to his response. Is he smiling back? Giving you the eye? Eye flirt a couple of times so that approaching him doesn’t come off as a surprise.

Then, if eye flirting has gone well, it’s time for the approach. Go up to the guy and say, “Hey, I’m Felicia.”

I mean, don’t use my name because that’d be weird. But you get it.

And what will his natural response be? Most likely, he’ll tell you what his name is and there will be an opportunity for you to have a conversation. It is literally as easy as that.

Now, the reality is, you can say whatever you want when you go make the first move. But you don’t have to come up with a Cirque du Soleil routine (a lá The Game) to keep the guy interested. A woman approaching a guy is uncommon, period. This means you have leverage, and there’s much less pressure on you to prove yourself and make the perfect first impression.

3. Dazzle With Conversation

Now we get into the meat of it. Of course, this is the next logical step in this sequence where we start to freak out again.

Omg, now that I’m here, what do I say? Am I interesting? Am I boring? Fuck, I’m boring!

We tend to forget what’s amazing about us the second we feel like we’re trying to impress someone else. Remember, this conversation is meant to answer the questions from earlier: Is this guy cool? Am I interested?

So naturally, what you say and the questions you ask should be designed to help you get a sense of this guy, while also drawing him to you. The first rule of a fantastic conversation is to focus on how you make the other person feel when they’re around you; that’s what keeps them wanting to stay for more

So what exactly does this look like?

First, employ the art of curiosity. Just like when you’re trying to figure out whether or not you’re going to buy that pair of shoes, you become curious about them first and then start asking questions.

Ask him about who he’s with (at the gym, bar, event, etc). Ask him WHY he loves the place. Ask him why he loves doing what he does.

When you ask “why” to anyone, they’re 10x more likely to reveal more about themselvesAssuming they have more depth than a goldfish. This is what helps get the conversation flowing and then moving at full speed.

And this is the part where you become selective. Notice what he’s giving back to you. Details or one-word answers? Questions about you in return? Does he start to get playful and tease you? Are you two just awkwardly staring at each other, nodding, and saying the dreaded, “Sooo…..YEAH”?

At this point–say 5 to 10 minutes into the conversation–it’s time to make a decision. Do you stay or do you go?

I actually suggest you do what may seem slightly counterintuitive.

For one, if it’s not going well, just leave. A simple “great talking to you” is just fine to get yourself off the hook.

But if the conversation is going REALLY well…I also suggest you leave. You want to leave at that moment you know you two are really enjoying each other. When that tension has been built, you excuse yourself and say…

“This was fun. Will I see you again?”

*Bats eyelashes, looks cute, etc.*

Now you’ve turned your approach into a challenge for him. If he’s into you, of course, he’ll try to see you again. Or, maybe he’ll tease back and it’ll be an intriguing mystery for now. But the key point here is, by exiting the conversation at the right time, you show that you have a life that excites you. The guy is cool and you may be into him, but you also have these girlfriends over there you want to talk to or that 3 mile run of your workout to finish.

And the best part about this?

You can do it over and over again. Approaching can be a fun game, where anyone you see becomes the most fascinating person in the room. Who are they? Why are they interesting? What makes them tick?  

It completely takes the anxiety and pressure out of talking to new people, and the bonus: you now have a richer, more exciting life to live, which is sexy as hell to a guy.

About the Author

Felicia is a charisma coach who helps people improve their social skills and dating lives. She’s been featured in Business Insider, Fox 5 News, and Fast Company.

Comments for This Entry

  • L Patterson

    This article was soooo helpful. I approach guys all the time for that initial, "Hello" and quick 1 or 2 sentences of "elevator talk" as I like to call it. They always smile back and seem curious but then I feel so much pressure and Dont know what else to do or say so I cordially end it quickly. The thing about asking "Why" questions is awesome. Thank u!!

    June 19, 2017 at 1:56 am

  • Kate

    A polite introduction will work wonders with me. I find it highly unattractive when people try pickup lines or say something like "Ayo, shawty".

    June 8, 2017 at 11:31 am

  • venessa roland

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  • Haibara loves Japan

    Great article, but what if you're too shy to do it ? Or just afraid of rejection ?

    August 13, 2016 at 6:37 am

  • John Galvin

    I keep away from girls from the city. Most are looking for a FREE ride

    June 27, 2016 at 12:21 pm

  • Brad Hart

    Great article Fel. Awesome to read empowering stuff that females can use to level the dating playing field. Now, how do I approach Matt Bomer? Specifically. Cause I saw him and I totally wimped out. So dreamy though.

    October 5, 2015 at 8:19 pm

  • Christopher Johns

    Good article, but I find it a bit perplexing. I don't know many guys that wouldn't be straight up flattered by any girl that approaches them. It happens so rarely.

    September 29, 2015 at 3:36 pm

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