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How to Flirt on a Date: 10 Expert First Date Flirting Tips

He knows how to flirt on a date and make her feel special

If you’re wondering how to flirt on a date, this is the guide for you. Below, you’ll find tons of first date flirting tips to help you woo whatever woman is lucky enough to join you.

Flirting is a key part of any successful first date. If you don’t flirt at all, she’s going to get the impression that you’re not into her or that you’re too scared to make a move. If you flirt too aggressively or in a weird way, it’s going to ruin the entire vibe of the date.

In any of these situations, the chances of your landing a second date are slim. That’s why it’s important for you to read this masterclass about how to flirt on a first date. It’s packed with basic flirting tips, as well as more advanced ideas on how to playfully tease a girl or compliment her.

By the time you’re finished reading, you’ll be a master at flirting on the first date. So, let’s dive in.

How to Flirt on a Date: Our First Date Flirting Tips

Here is a short list of basic tips for how to flirt on a date that will never serve you wrong.

Keep eye contact

If you avoid eye contact when flirting or look away as you’re saying something flirty, that’s a clear sign that you’re not confident in the words you’re saying.

The eyes are the window to the soul, and they’ll reveal the truth of how you actually feel. Strong, relaxed eye contact can make a woman’s heart melt without you saying a word because it shows you’re comfortable in the tension of a first date. A lack of eye contact can remove the impact from any words you are saying.

As cringeworthy as it may sound, it’s honestly worth practicing saying flirty lines in the mirror and keeping eye contact with yourself. This will make it easier to do so with a woman on a first date.

It’s not what you say, it’s how you say it

Your voice is a powerful weapon when it comes to flirting on the first date and beyond.

The way you say something will have a huge impact on how the woman receives it. For the maximum impact on a woman, you’ll want to speak slowly and make sure to pitch your voice with a downwards inclination. Avoid laughing too.

This is the most seductive way of speaking. For an example, watch how James Bond speaks to anyone in any of his movies. It’s a rapport-breaking tonality but mixed with a compliment, like a cupid’s arrow to a woman’s heart.

For an example of how not to speak to a woman on a first date, take note of how servers speak to you at a restaurant. Most likely, they will talk quickly with an upwards inflection (rapport-seeking tonality). That’s great if you want to appear friendly and harmless, but not if you’re trying to seduce a woman.

When flirting on a first date, subtlety is key

Flirting is a dance. It involves push and pull. It puts out the idea that you may be attracted to her but also leaves an element of doubt.

That doubt is what inspires a woman to pursue you more. Women love the emotional rollercoaster of not knowing how a love story is going to end. It drives them wild with anticipation, and this is what inspires them to go home with you at the end of a first date. They need to know how the love story ends.

If you flirt too aggressively and make it too obvious that you want her, it spoils the ending of the love story and ruins the emotional rollercoaster. That’s why subtlety is key with flirting.

“You look great in that dress” is better than “Oh my god, I just want to take you home and bang you right now”, for example.

Push-pull flirting is a great way to ensure you keep this subtlety. With every compliment (pull), you add a slight signal of disinterest (push). There are some examples of good push-pull lines later on in the article.

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Teasing is a great flirting tool

Teasing is another way to introduce an element of doubt in a woman’s mind and create that emotional rollercoaster she craves.

It’s not mean or nasty to playfully tease a woman. This is what most friends and family members do to each other. It’s actually a sign of close friendship when you feel comfortable teasing each other. It also shows that you don’t think the other person is “above” you in any way.

The key to effectively teasing a woman is not to target something that is actually true, and therefore likely to actually upset her.

Touch is an essential part of flirting

It’s important to touch a woman when you’re flirting. Physical touch turns on a woman just as much as it does a man, plus it will help you understand how comfortable she is around you.

The key to successful physical flirting is to start slow and innocent, see how she responds, then ramp it up if she’s comfortable. If she tenses up, you’re moving too fast. If she embraces your touch, you’re ready for more risque moves.

This is the secret to knowing when a woman is ready to be kissed or invited back to your place for more intimate physical exploration.

Pay attention to how she responds

This is crucial when flirting physically, but also when you throw flirty lines at her.

If she tenses up or cringes, you’re being too aggressive. If she enjoys what you’re doing, feel free to ramp it up even further.

Don’t be that guy who turns his flirting up to 100, with no empathy for how it makes the other person feel.

For an example of what this looks like, watch the cartoon “Johnny Bravo”. Behave like Johnny, and you’ll be turned down just as often as he is.

It’s not gentlemanly to forego flirting

This might be the most important of all the first date flirting tips you ever hear. Even if you’re looking for a serious long-term relationship, it’s important to flirt on the first date.

It is not gentlemanly to treat her platonically. In fact, that’s likely to annoy her. She turned up on the first date because she was attracted to you. By not flirting at all, you kill that attraction completely.

For her to feel that suspense of “does he like me or not?”, there needs to be some hint of flirtation. Otherwise, she assumes you’re not interested or that you’re too much of a coward to show it.

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How to Compliment a Girl on the First Date

It’s important not to overwhelm a woman with compliments unless she’s earned them. If you supplicate to her, you run the risk of coming off as a people-pleaser or making her feel like she’s above you.

Here are three examples of lame compliments.

“Oh wow, you study photography? That’s so cool!”

“Wow, I love your blonde hair. Blonde hair is awesome!”

“That’s so amazing that you have a dog!”

There is objectively nothing impressive about any of these achievements. Literally, millions of people have blonde hair or a dog. Hundreds of thousands have studied photography at some point.

Over-complimenting people can be a good way to make friends, but it’s an awful way to make someone attracted to you.

Complimenting her eyes, her lips or anything she’s born with is also not a great idea. These compliments usually go straight over the heads of beautiful women. They’ve heard that they’re beautiful a million times before. But it’s all skin-deep, so complimenting it doesn’t penetrate their heart as deeply as you’d like.

Yes, you can compliment her outfit or tell her she looks great at the start of the date. After that, it’s far more impactful to compliment her personality or her achievements

Even then, you don’t need to go over the top with your compliments. All this does is signal that you don’t usually hang out with girls as special as her - and that’s a great way to make her feel like you don’t deserve her.

How to Playfully Tease a Girl

The keys to playfully teasing a girl are:

  • Smiling, so she knows you’re kidding.
  • Eye contact, so you can see if you want too far.
  • Don’t pick on things that are actually true, as you may upset her.

A great way to ensure you don’t go too far is to focus only on silly playful things that aren’t true. You can go over the top and exaggerate these points as deeply as you like.

“You seem like the kind of girl who will murder me in my sleep.”

“You tell the same type of jokes as my Grandma.”

“Are you the type of woman who will down 15 cocktails in one night, then wake up in a gutter?”

You can use the push-pull technique described earlier as an effective way to tease a girl too.

“You can stay over, but only if you promise not to smother me in my sleep.”

“You can meet my friends, but don’t bore them to death with your Grandma jokes.”

“I’ll pay for the drinks, but promise I won’t have to call the ambulance to get your stomach pumped.”

As you can hopefully see, the more over-the-top you go with your teasing, the more obvious it will be that you’re kidding. Plus, it will usually be funnier too. Exaggeration is an effective comedic tool.

If you do go too far and actually upset her, don’t hesitate to tell her it was a joke. If she remains upset, it’s OK to apologize. These things happen sometimes.

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How to Flirt After the First Date

There really doesn’t need to be any difference in your flirting strategy on the first date and after it. If she agreed to come on a second date with you, that means you did a great job on date one.

The one thing to bear in mind is that you may have to start from scratch as far as the intensity of the flirting at the beginning of your date.

Just because she was receptive to sexual talk or playful slaps on the ass last time, that doesn’t mean she’ll be immediately excited to engage in that again. Women are very emotional, and their receptiveness to your flirting will be based on how her emotions are in that moment.

Eventually, there will come a time when it’s obvious you both like each other. At that point, the mystery has disappeared and you won’t need to be as subtle with your flirting. But you should never completely stop flirting with your casual partner, girlfriend or wife.

When you do it properly, it will always give them the tingles.


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