5 Easy Mistakes To Make While Flirting With Someone

5 Flirting Mistakes Header

Hiya. I’m Jillian Boyd, and I’m actually bloody terrible at flirting. Some of you might disagree, but trust me, I am. And I am sharing my knowledge with you today, dear reader, because I like you and I don’t want you to be terrible at flirting.

This won’t make you a world class Casanova, mind. This advice is in no way gospel. But if you see anything that resonates, feel free to interpret and use in your own way. Anyway, here are some mistakes that you’d be best to not make while flirting, in my opinion. (Milage may vary, as such.)

Setting the scene first – picture yourself at a party. Maybe a mate has thrown a housewarming do, maybe it’s a party at a club/bar. You’re doing the things you usually do at these sort of things, whether it’s socialising or sitting somewhere quiet with a drink. Suddenly, you spot someone you actually quite like the look of.

Mistake The First – Letting the initial eye contact go into weird staring mode

And success! They’ve spotted you too. There’s a smile from them, a smile from you. But then the other person turns away, and you’re still looking at them, maybe a bit too intensely. Or maybe you turn away, and this other person is still looking at you – staring, even – and you don’t notice until you turn back in their direction to see them still looking at you.

Avoid by keeping the initial eye contact brief. Look, smile, and then continue with what you were doing. Chances are that you’ll spot your flirtee several more times over the course of the night, which allows you to make more brief eye-contact and (if you’re up to doing so) going in for a conversation.

Which leads to possible mistake number two.

Mistake The Second – Fucking up the opening conversational gambit

Otherwise known as the “Chat-Up Line”. You’ve probably heard many of them in your lifetime – possibly in a “Ten Worst Chat-Up Lines” line-up in a magazine or TV show of some sorts.

So, you’ve achieved going in for a conversation. You’ve probably already gotten past the Hi/Hey There bit of it. Now, what follows will be key for both of you. Ideally, you’d want to aim for a casual, flowing conversation that won’t make you want to bolt out of there with your glass of wine still in your hand.

Ideally, you’ll aim to not utter anything along the lines of “The time is two-flirty and the date’s with me, babe.”

Avoid by going in casual. Ask their name, make some small talk, put your feelers out and see if you hit it off. Don’t go full-on HI HAVE SEX WITH ME M’KAY, or anything else that will send them straight out the door and back home.

Mistake Trois – Not being yourself

Okay, I know how much “Be Yourself” sounds like inspirational cack to some, but it’s bloody true in most situations – certainly in flirting with someone who you’ve taken a shine to.

“Not being yourself” can be interpreted in a manner of ways, from acting against your actual day-to-day persona (eg. being cocky and brash while you’re actually modest and lovely) to actually claiming you’re an entirely different person.

eg. Chandler Bing claiming he’s a Kennedy when he’s flirting with a girl.

Really, just be yourself, in as much the situation allows you to. Try to relax; try to be natural.

Mistake IV – Not taking initiative/Assuming too much too soon.

So, you’ve been doing alright throughout the night with your flirtee. You’ve chatted, you’ve laughed, they turn out to be a lovely and not at all horrible person. You’ve maybe even danced with them. Doesn’t mean that at the end of the night, everything will be a-okay.

Don’t assume too soon that this person will ask for/give out numbers, or anything relating to actually seeing you again. Remember, you’ve only met this person about four hours ago, and all you know about them is maybe their name, job and if they’re a crap dancer or not.

What I’m saying is that you don’t know their situation beyond the walls of the environs you find yourself in. If you’re into this person, at least to a level of “I fancy meeting up in a place that’s less crowded so we can have a decent chat”, ask if this is a thing they would like to do as well. If it’s just as friends, then good, you’ve made yourself a new friend. If it’s a date, then good, you’ve got a date.

Mistake The Fifth – Assuming the kiss will happen.

So, it’s the end of the night. So far, you’ve managed to not creep them out with your eyes or words. You’ve managed to come off as your natural, lovely self and you’ve not made an arse out of yourself by assuming that there’s a relationship in there somewhere too quickly.

Thus we come to the goodbyes.

No matter what has happened up until this point, don’t assume that there will be a kiss. Doesn’t matter if you want one (however badly). There is nothing more terrible (and, sometimes,painful) than going in for a kiss with someone you rather like and then having it turn awkward because they’re not ready to give you one.

And an extra pointer, just because I loves y’all:

You are more than allowed to walk away.

You know what I mean. If your flirtee turns out to be an absolute dipshit, excuse yourself and walk away. We all have our limits.

Again, this is in no way intended to be taken as gospel, but I hope this was useful, in some way or another. If you’ve got any more flirting mistakes to add, or you want to share your own story, feel free to leave it in the comments. But remember, politeness and such!

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  1. The last step is the hardest for me, I feel bad about walking away from someone, not wanting to hurt their feelings

  2. And perhaps a #6 – Don’t be touchy-feely. I, for one, am totally creeped out by this type of ‘flirting’. The conversation might be lovely, he might have the absolute best of intentions, but when a guy I’ve only met an hour ago invades my personal space by casually putting a hand on my knee or playing with my fingers, I’m done. No recovery.

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