How to HELP Your Shy Guy Friend Make the First Move

So, you’re secretly in love with your guy friend, Shane. And you have the inkling that he feels the same. You want him to make the first move (yay!), but you’re growing impatient. Or he’s leaving for college…

or lets just be honest, your hormones are raging and you just want the boy to kiss you already!

This is something like what happened to one of my readers… What did I tell her to do? Read below to find out:

There are bold ways to hint (“bold hint,” kinda an oxymoron, but it’s actually very fitting!) to help him “make the first move.” Yes, he may be shy, but don’t let him get away with having to make the first move just because he’s shy. He needs to man up just like every other guy.

You could be bold and ask him,

“Has the thought of kissing me ever crossed your mind?”

You have to say it, not in a begging kind of way, but with a curious, mischievous look in your eye. One that says, I want to know the answer out of curiousity but I don’t care if you say no. That is key to playing this off with confidence. Wait for his answer. See, this looks like you’re making the first move, but in actuality, you’re not telling him you’ve thought about it. You’re just trying to tease him with the idea, and see if he’ll use the opportunity to make a bold move, like actually kiss you.

Worst case scenario, if he says,


just play along with it,

“Oh, come on:) So you really think it’s possible for guys and girls to ‘just be friends?’”

This way you don’t take it as a “rejection,” because it isn’t a rejection. I mean you are friends so it’s just asking his opinion. But if he does say no, this is your way of knowing he isn’t interested in you in that way. Throwing it out there like that will show your confidence but also give you a chance to give him an “in.” He’ll be thinking, hmmm, does she like me? What is this? But he won’t know for sure.

That’s the difference between “boldly hinting,” and actually “making the first move.”

    If he knows without a shadow of a doubt that you’re into him, then you’ve crossed the line and officially “made the first move.” But if he can’t make that assumption because there’s not enough evidence, and he’s still left somewhat in the dark, then you know you’re doing the right thing and just “boldly hinting.” It still gives him the chance to make the first move.

If he says,

“Yes, I have thought of it,”

Put him in the limelight and make him squirm a little. Ask him,

“Like, have you thought about it once? or like, periodically?… or like it keeps you up at night?”

and smile teasingly.

And if he’s like,

“Why do you ask?”

or if he’s like,

“Have you thought about it?”

Tell him,

“I’m the one doing the questions here mister.”


“Don’t turn this around on me!”

Then pause for a second and tell him,

“All I can say is, I wouldn’t be completely opposed to it.”

Then smile and completely change the subject.

“Hey, wanna go get some ice cream?”

Why change the subject? So he can go home and soak it all in and contemplate what he should do next. And wonder, and be puzzled, and realize even more so, what a cool, confident chick you are:)

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Article written by:

I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

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  1. u know who

    i like that picture … for obvious reasons. 😉

    • MidoriLei

      u know who,

      You know I posted that pic just for you too!!! too bad… the love of your life can’t be your bestie cuz I am!

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