Chris Castig Chris Castiglione is an educator. His mission is to use storytelling as a tool to inspire positive change in the world.

How do I flirt?

2 min read

HeTextedThis post is part of a series of questions I answered during my time at HeTexted. Hundreds of girls asked me relationship advice, and I responded.

On May 22nd, a girl asked me…

Well Him & I have been best friends for 4 years now, but to be honest I like him, just a little? 🙂 I’m not popular but I do have lots of friends, but there are 3 problems:

1- He hangs out with me, but he hangs out with the popular girls too

2- I don’t have a great looking body, I describe myself over-weighted bt most of people say I’m not

3- We, ALWAYS sit together in all of our classes, but instead of talking he looks at, I ask him what? but he just smiles and it makes me think that I’m a funny-looking person (in a bad way)

Btw, he’s not a player type, yes he has lots of friends whom are girls but he doesn’t date with any of them

sooo what should I do? should I flirt? if I should…HOW??!?! pleaseee help! 🙁

My advice…

As far as ‘does he like you’? Neither of us know yet.

And so yes… ask him out, make a move, flirt.. all of that! Be bold! (Easier for me to type then to do.. but I’ve done it, and afterwards it feels so good either way it goes).

Flirting? Flirting is often referred to as a push/pull between a man and woman. Basically it can involve light teasing, and just a bit of role play fun. So (just one example) if he said something that you didn’t agree with like “I’m going to the Giants game, they’re my favorite”, instead of just agreeing or laughing or whatever you could tease him, “Wow, this just isn’t going to work out between the two of us. I mean, I thought I knew you. We’re getting a divorce…and I’m taking the kids.” I’ve used silly stuff like that a lot, it usually works if you deliver it right. And it’s fun, you could have that role playing thing go on for weeks.

Flirting also involves touch. Making excuses to touch… like thumb wrestling. Real wrestling. Back massages. etc.

Heres an article and book on flirting that might interest you…

One more thing. And this is important.

Theres a problem with those problems you listed: that’s all YOUR reality. As in, those are only problems if you believe they are problems. Look, I’m not trying to be all socially-blind to the world we live in… but confidence and the wherewithal to put yourself out there and take risks goes a long way.

You can do that on your own. But it’s always great to have a role model, whether it be someone on TV or (ideally) someone you know (like a friend or older sister) who can guide you, give advice and help you with low self esteem regarding these “problems”.

Psychologist sometimes refer to these thoughts as “limiting beliefs”… they are things you tell yourself to limit your success. I have them too… we all have them. And sometimes when I need to confidence to go up to a girl and tell her I like her.. I’ll meet with my best friend Alexis, he makes me feel like I’m the funniest person in the world and way cooler (than I may actually be). And then after hanging with him I’m all like “Cool! I’m ready to go into this situation head first and ask this girl out.. if she says “no” or laughs? Whatever… someone still thinks I’m the coolest person in the world” .. and so that helps.

Look. You’re going to do this, try your best. And whatever happens..write back and at least I’ll tell you that you’re awesome! Haha.

Best of luck, let me know how it goes!



You are a real bro!!! thank you so much!! I’ll try to do my best..But it can take time 😀 but I’ll write you back when something happens thank you!! xx
Chris Castig Chris Castiglione is an educator. His mission is to use storytelling as a tool to inspire positive change in the world.

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