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How To Flirt On A First Date With Her: 5 Expert Tips

July 1, 2024
▪ 10 mins read

If you’ve had one too many dates end with a message from her saying, “you’re a nice guy BUT…” you may be wondering, “how to flirt on a first date with her?” 

As a dating expert, I know just how hard even getting to the point of that first date can be: Hours of swiping on dating apps, messaging conversations fizzling out, and the idea of meeting her in real life feels daunting…

So I get that you don’t want to fall at the first hurdle, and instead we need to nail your first date! 

In this blog, I’ll share: 

  • Should you warm her up for your date with flirty messages? 
  • What do you say when you first see her? 
  • What's an easy way to create that sparky 'banter' women love on your first date? 

Instead of giving you a bunch of lines that you’ll struggle to implement, and (no offence) probably use totally out of context; I’ll be using this blog to give you a play-by-play on how to flirt on a first date by showing you what flirtation method is appropriate and when.

My goal is to coach you to be the socially sophisticated, confident communicator that women love… and to get you results! So let’s get started with how to flirt on a first date with her!  

Tip 1: Forget flirting until you’re on the date

Poster saying Expert tip 1 Forget Flirting Until You're on the date

I get it. After probably more than a few blow out first dates, you think you need to ‘warm up’ the connection with her with some sexy messages before you flirt on a first date. (Being totally honest with yourself, are you also trying to get some flirting out of the way on messaging as it feels easier than communicating with her in person?) 

Whilst I 100% understand your reasoning, trying to flirt too much with her using messages before your first date may turn her off, and create the exact outcome that you don’t want.

Let me explain: She is on a fundamentally different timeline in her attraction to you. For the majority of guys (who aren’t famous, or who don’t own a yacht) women will walk into a first date with you thinking, “I wonder if I’ll like him, or whether this will be a total bust?” 

If this is her frame of mind, the last thing you want to do is increase the pressure on her by coming across as someone who really desires her. Anything that even somewhat resembles a message like this will be met with an emphatic “yuk” from her:

“I’ve been thinking about our date. Are you ready for fun and adventure? Adam xx” 

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So action steps:

  • Limit your use of emojis
  • Drop the kisses
  • Message her the day before the date to confirm, but minimise other chat
  • Short and direct messages work best

“Looking forward to Saturday - see you at 6!” 

Messages like these help her to feel you’re on a level playing field when it comes to attraction. The short and direct tone is also interpreted by her as casual yet masculine; and this sets the stage far better for how to flirt on a first date. 

Tip 2. Keep compliments simple 

Poster saying Expert tip 2 Keep Compliments Simple

When you first meet, on your first date, both of you may be feeling somewhat hesitant. Watch out at this moment for if you have a ‘people pleasing’ instinct that goes into overdrive.

Particularly if you’ve had some bad first date experiences with a woman seeming not to understand that it was a date (not just a catch up between acquaintances) you may be tempted to over compensate here with A LOT of compliments eg:

That dress looks lovely on you! 
You look absolutely stunning! 

Notice that both of these compliments don’t do the job of flirting on a first date. Flirting on a first date is about playing with the uncertainty of whether you like one another, and are compatible. 

If it’s clear from the get go that you 100% want and desire her (with minimal contribution from her) this isn’t how to flirt on a first date. 

Instead of over complimenting, simply say “you look great” then move on! Don’t dwell on complimenting her; as once again this will feel like pressure to her. 

Instead focus your first few minutes of the date on having a “normal” chat this will help her to relax. 

Your mindset here is to explore the connection with her and have fun, not to have an agenda. 

Tip 3. Tease her, once she’s comfortable 

Poster saying Expert tip 3Tease her, once she's comfortable

When and only when she’s relatively happy and relaxed then you can start to flirt on your first date by playfully teasing her. 

A lot of men that I coach get stuck at this stage of the interaction. They know how to make her feel comfortable, but by staying in this zone the whole date they miss out on the opportunity to create a spark with her. Remember if you don’t flirt on a first date with her, you will be on a one way ticket to that, “you’re a nice guy but…” message.  

So how do you flirt on a first date? Start with some playful teasing. All teasing really boils down to is:

  • Sharing your true opinion and not just agreeing with everything she says. 
  • Saying it with a smile because you’re relaxed and having fun, it’s only a first date! 

Some examples of “playful disagreement” aka “teasing her” could be:

“Oh no you’re not a Bridgerton fan are you?” 
“Yikes, does this mean one day you’ll be dragging me to a yoga class?” 
“I knew you were a closet Swiftie!” 

The key is to tell the truth, in a fun light-hearted way and show you’re not hell bent on impressing her. 

Women don’t like men who obviously shift their opinion to impress a woman, this shows that you don’t value your life as it is, and in fact will bend over backwards to “get” her. Again this isn’t how to flirt on a first date. Instead go into your first dates in a more neutral mindset that you’re also there to figure out if she’s right for you. Just swapping your mindset around can do wonders for your natural flirtation skills. 

Tip 4. Show leadership

Poster saying Expert tip 4 Show Leadership

I coach women as well, and I can tell you now, forget the fact we live in a modern world: Women will desire you more if you plan the date! 

When you’re in a long term relationship, you don’t always have to be “the boss”, but at that attraction creation stage taking the lead is really helpful. 

When it comes to how to flirt on a first date with her, a huge part of this will be creating the right environment where she feels secure enough with you to relax and go with the flow.

A man who:

  • Doesn’t have a clear plan for the date.
  • Can’t be spontaneous as he lacks confidence in his decisions.
  • Constantly looks to a woman to decide everything (hello people pleasing!)
  • Tries to plan everything to fit in with what he thinks she’ll like (instead of introducing her to what he likes.)

Won’t create the right environment to flirt on a first date. She will sense his insecurity and feel like she can’t properly relax around him. When you’re building attraction with her, women will be drawn to men who they feel they can trust. 

Unless you step into a leadership role (at least temporarily) and execute a plan that she can follow, the flirting dynamic is off from the start. 

When it comes to how to flirt on a first date, the form of flirtation I’d call “leading” doesn’t have to be heavy handed it could simply be:

  • Date planning “hey, there’s this cool spot I love let’s go here…”
  • Presenting solutions, “okay this place sucks, my bad let’s get a cab to another place I like just down the road.” 
  • Stage managing the date, “you grab a seat I’ll order us drinks.”
  • Having an opinion, “you’d be crazy not to try the margaritas here.”
  • Being chivalrous, “you take this seat, it's got the better view.” 

Tip 5. Maintain some mystery

Poster saying Expert tip 5 Main some mystery

As I mentioned right at the start, when you’re flirting on a first date with her, you have to always sub-communicate, “I haven’t made my mind up about you yet.” This should also be the truth (!) there’s lots of gorgeous women in the world, you need a connection with her for you to want more dates. 

There’s few bigger turn offs than when a woman feels like you’re scheming away trying to make her like you. If instead you show her that your attraction to her is variable based on what she puts into your dates, and that you too have standards, it makes her more excited to get to know you. (She may even start chasing you, if you learn to lean out of your dates with her at the right moments.)

Trust me, read any romantic novel and a huge chunk of the plot will be based around, “will or won’t they get together?” 

Use this trope of romance to work some flirtatious language into your dates. Instead of pushing her to see you again, or go back to your place (when there’s not a huge amount of sexual desire in place) keep things open ended. 

Try wrapping up your first dates by saying:

“We should do this again sometime” 
“Let’s do this again soon” 

This shows that you’re confident enough to make your intentions clear with her, whilst creating some uncertainty as to when you’ll next meet, which takes the pressure off

Again this is a foundational way that you flirt on a first date with her, by giving her breathing room to feel attraction to you at her own pace. 

If you want to nail your dates with women - discover more of my coaching programmes here.

How To Flirt On A First Date With Her | FAQs 

How can I impress her on a first date?

Never go onto a first date with a woman overthinking how to impress her. If a woman senses that you’re not being authentic, but are bending over backwards to impress her, this will make her lose interest in you. Instead, follow these simple first date tips to naturally create attraction: 

  1. Plan your dates. This demonstrates thoughtfulness and that you’re comfortable taking the lead. 
  2. Keep your date short and sweet. A 2.5 hour date is just about right to give you enough time to connect, without overwhelming her. 
  3. Dress sharp! Good personal style and presentation will always impress people. 
  4. Relax your body language. Open, relaxed body language demonstrates confidence. 
  5. Make great eye contact. This is the easiest way to forge a connection with her. 
  6. Smile. This shows that you’re at ease! 
  7. Offer to pick up the bill. However, you don’t need to go somewhere expensive, it’s the gesture that counts. 
  8. Be playful. A first date is an opportunity to have fun with her. 
  9. Give a thoughtful compliment. Tell her 1 thing you genuinely like about her. 
  10. Be authentic. The less you try to impress her, the more you are yourself, the better the date will go! 

How to be flirty on a first date?

Being flirty on a first date helps to communicate that you have romantic expectations for this interaction. Being “flirty” is also a form of communication that everyone can tap into, just follow these simple tips:

  1. Be bold. Don’t hold back on your opinions, taking a few risks in your conversations with her will create a flirty atmosphere on your dates. 
  2. Be yourself. The easiest way to tease her is to allow yourself to share your true opinions. 
  3. Be playful. One of the best parts of flirty first dates is that they’re an opportunity to have fun!
  4. Be thoughtful. One meaningful compliment is worth 100 meaningless ones.
  5. Be genuine. Smiling and eye contact is a great way to show that you’re sincere. 
  6. Be tactile. If she’s receptive, start with a brief touch to her arm to test the water. 
  7. Be organised. Create a plan for your date, so that once it starts you can be present and have fun. 
  8. Be spontaneous. If something doesn’t go to plan, simply state that it wasn’t what you expected and make a new suggestion. 
  9. Be prepared to rock the boat by teasing her, this is often what creates the spark! 
  10. Be daring. Tell her if you’d like to see her again, or kiss her! 

How do you build chemistry on a first date?

You can’t guarantee chemistry on a first date with a woman; that’s because she has a role to play in creating the spark too. Great first date chemistry is about both of you showing up, ready to get that click. That being said there’s a few things you can do to give yourself the best chance of sparking attraction with her: 

  1. Have a plan for your first date. There’s nothing exciting about, “so what do you want to do?”
  2. Share your true opinion with her. People will feel stronger chemistry when there’s a mix of agreement and disagreement on their date. 
  3. Keep things light hearted. First dates aren’t that deep, being relaxed and casual, is much more appropriate behaviour for a first date. 
  4. Relax! To create chemistry on a first date you need to be in the present moment with her. 
  5. Tell her what you like about her. A specific compliment will create a moment of intensity but that can also create a spark.
  6. Avoid showering her with compliments. This will come across like you want something from her, instead 1 compliment is enough.
  7. Ask questions you actually care about the answer to. 
  8. Test out physical touch. Start with a light touch to her arm, or sitting a little closer, to see if she wants more physical intimacy too. 
  9. Make great eye contact. This is an easy way to create chemistry! 
  10. Pause! Don’t fear first date pauses, they can become great moments to sense a spark. 
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