Conversation Skills
For Men

How To Flirt Without Being Creepy

July 6, 2018
▪ 4 mins read

Conversational do's and don'ts

How to flirt without being creepy is possibly the biggest mental barrier for men to overcome when they want to approach a woman.

Men and women are full of passion and desire, they want to love people and they want to be loved. However, people who can skilfully talk to strangers rarely harness this powerful energy. That feeling of liking someone but not knowing how to talk to them leaves people feeling frustrated through regret, and this can lead to a build-up of anxiety for the next occasion.

I remember once being in a club in Auckland, I observed a gentleman hitting on all the women with about as much success as Danny Dyer on University Challenge.

I respected the fact that he was trying but the way he was doing it was not respectful.

On public transport, I have seen guys walk up to a woman and from about six inches away from her face say, "so what’s your name". Talk about space invading and being creepy while attempting to flirt.

Why are these men getting it so wrong?

Learning theFive-Step System, which we teach atThe Hayley Quinn Academy, makes talking to strangers a really enjoyable process. You learn boundaries between being creepy and flirty.

It will open opportunities. A client I was coaching last night approached a woman with confidence, acknowledged what he was doing would be considered unusual and expressed romantic intent in a way that was assertive but not creepy.

He then took the women out for date later that night. This is what can be achieved just by learning a few nuances to the conversation and body language.

Before I get into the dos of how to flirt I want to start with the don't's.

1. Personal space- do not get too close

This is the most common issue I see when coaching people. Luckily it is easy to fix. The reason why it puts people off so much is that it signals neediness and lots of approval.

Its seems to be a subconscious way of trapping the person so they are forced to give you a positive reaction but it has the opposite effect.

Also, something that men generally don’t consider is that women feel that sense of physical danger much more than men do.

If a man sits close to another man on a train, the guy might find it annoying, but if a man sits too close to women it will most likely make her feel threatened and uncomfortable.

2. Less smiling

It would like to make clear that smiling is fine especially later on in the interaction. However, smiling too much too soon does convey neediness.

Not necessarily neediness for that woman but needy for the conversation to run smoothly. What the smiling shows are a need to keep her there. It makes the guy look like he’s not relaxed around her.

On my first couple of sessions with a new client, I will try to reduce the smiling in the early parts of the interaction.

It feels strange for them at first but then they see the difference if they appear more relaxed at the beginning of the interaction.

3. Do not linger

This may seem like it doesn’t need to be said, but I have seen this happen a lot.

I notice that when a guy has said his initial opening sentence, he will then continue to sit with her.

This is an absolute no-no. The problem that arises again is that she doesn’t know when you’re going to leave the interaction.

She has no idea when you are going to stop talking to her.

If you feel like the vibe is good, call it out and ask her if you can join her. Also if you give yourself a time constraint in early on this will make her feel much more at ease. Such as, "I have just got to get back to my friends but I just want to quickly say...".

Now the don’ts have been explained, here is how you can appear charming and not needy.

4. Acknowledge

Acknowledge the situation and call it out. Stopping strangers and talking to them is unusual, convey social intelligence by acknowledging this by justifying why you have come over.

A few hours before I wrote this I approached a lovely lady on the Strand in Central London.

She was walking along eating some chips, so I went over to her and said, "excuse me I know you’re eating those delicious chips, but you walked past me and had to come and say hi because I think you are very attractive."

Because I explained why I went over she relaxed and we got chatting about what she was studying.

I ended up taking her number because she felt comfortable with me from the start.

5. Put a time limit on it!

I have already spoken a little bit about this earlier on, however it is very important.

Adding a time constraint is a very good way of immediately making the person feel more comfortable with you.

Even if the vibe is good, if it is not clear when you are leaving this will make her feel uncomfortable and anxious.

By saying, "I have somewhere to be", and then continuing what you were saying, this squashes her worries about trying to get rid of you.

6. The conversational Riff

Talk about subjects in which you know about. Start by saying "that kind of reminds me of..."

Then refer to a subject in which you are well informed. You will be more likely to appear confident and assertive when you know a bit about the subject.

She will then feel more likely to open up about things she is interested in. And you will most definitely flirt with her without being creepy.

Remember women want to meet you and sometimes struggle to tell who the good guys are, so don't hold yourself back from approaching. Instead, we want to work with you so that you can meet more women in a way that is smooth and respectful: start here with a free 3 part video series on how to approach and get out there :-)

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

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