Should I make the first move on a guy I’m interested in?


Dear Megan,

So, there’s a guy, (30), that I’ve been interested in for some time now, (I’m 23). We’ve known each other for about 8 years, but have never been close or anything. I always found him attractive but never pursued anything until earlier this year when we ran into each other randomly and decided to grab lunch together. We talked and got to know each other a little better and I realized he and I have so much in common and that we have very similar personalities.

We communicate more than we used to now, mostly over Facebook, but it hasn’t become flirtatious or anything. He comments on pretty much every one of my posts, and people are always asking me “who is that guy who’s all over your Facebook page?”

He and I have both been single for quite a while, but I know that both of us are looking to get back out into the dating world. I don’t know if he’s interested, but I think even if he isn’t now, he might be if he knew I was interested in him…

I asked him to help me out with my blog because he’s good at that kind of stuff, and he said he’d love to, so we’re going to be doing that next week, and I’m considering asking him if he’d like to grab dinner or a drink afterwards… not necessarily a date, but at the very least an excuse to spend more time getting to know each other. But I’m afraid that might be too forward.

In my experience, whenever I’ve pursued a man or tried being direct about my interest in them, they get scared off, even if they already liked me… It’s like they immediately lose interest if winning someone over is no longer a challenge. So now I’m deathly afraid of making my interest known, and I feel like as the woman I have to just sit around and wait for men to ask me out. But I also worry that he may not make a move if I’m coming across as disinterested. So I guess I would like to ask two questions:

Have you ever made the first move, and was it successful?

-Confused and Bashful


Dear “Confused and Bashful,”

Christ, the last guy I made the first move on – (and by “first move” I mean said “hi” to first) – I had to marry to get rid of, haha… So yeah, it can be “successful…” if done properly.

In the world of financial trading it is said that “A decision NOT to trade (a stock) is also a trading decision;” and it seems that you, my dear, have yet to learn that when it comes to being a woman, a decision NOT to make a first move is also a first move.

You see, guys don’t become interested in a girl once they know she’s interested. That’s not how they work. They know what they like. They know what they want. And they’re either interested in you, or not.

Consequently, as a woman, your “first move” is simply to expose yourself to him – (and I’m not talking about in a snapchat kind of way, either, despite how effective that is scoring a Netflix-and-chill kind of night) – which you’ve done.

If he’s attracted to your beauty and/or brains it won’t take long for him to realize it. And you definitely won’t have to try and sneak your way in through the friend-zone – (I shudder at the thought!). Resist your customary urge to pursue – (good God, resist it!) – and just keep on going about your business and being your fabulous self.

Know that this is not about passively sitting around and waiting for men to ask you out, either. This is about patiently and actively learning to like the men who like you enough to risk rejection and ask you out. Trust me, you’ll need that level of passion and conviction in a guy down the road for you two to get through tough times.

So have faith, chica. Faith that your guy will see you, want you, and do what he has to do to not let you get away. Don’t chase, chill… And get one of those big, red “easy” buttons. That way when you’re resting comfortably in the arms of your future boo you can lean over, press it, and hear the sound of the automated guy saying, “that was easy.” Best of luck.

-Megan 🙂

For my story check out “The Care and Feeding of Sex Symbols” here

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Note: As this column is designed to be a judgement-free zone, only those who have been, (or know someone who has been), in a similar situation are invited to comment; especially if the question is unorthodox or hard for one to relate to.  And for even more relevant insight, those seeking answers are always encouraged to go within.


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