How to have a fun first date, every time

Couple enjoying a fun first date and having fun dating.

A fun first date equals a second

Fun is almost universally undervalued and under-represented on first dates.  Too many guys and girls seem to think that the purpose of a first date is to get to know someone – when it’s really not. The purpose of any date, but especially a first date, is to have a fun first date. You need to have FUN with someone so you can truly see if you feel attracted to each other. If that goes well, then you’ll have the rest of your lives to exchange facts and back-stories with each other.

On a first date, fun trumps facts, hands down.


This material that I have to share with you on the topic of making dates more fun is PURE GOLD.

It will enrich your first dates so much that once you’ve done it and seen what it can do, you’ll avoid the tired and really lame ‘getting to know you’ type date questions like a wet seat on a bus.

So take note, and even more importantly, DO THIS STUFF on your dates and enjoy the results for yourself. Make it your mantra to have fun first dates. And don’t worry, you can thank me later, or just post your comments below.  I’d love to hear about how you’ve put this stuff into practice.

Alright, let’s get into the material. Here are a couple of surefire ways to amp up the fun-factor in your dates:

1.      Be fun and playful

2.      Do fun and exciting activities

Let’s break these down further and take a closer look at each.

Why should you bother being fun and playful on your dates?

The two tried and tested reasons for being fun and playful with her on your date, are that she’ll:

1) Enjoy herself and your company more during your date.

2) Find you more attractive, based on your fun nature, playfulness and sense of humour.

In DateSchool, we always talk about sense of humour, fun and playfulness as some of the most attractive traits that will draw women to you. Scientific studies over the past five years increasingly support this view too. Most recently a 2015 European study added further support to the US-based findings in this area, suggesting that across the globe, women are attracted to fun and playful men. I encourage you to read this study here.

Another study, when looking at women’s levels of attraction towards men, found that fun and playfulness rank even higher than physical attractiveness and earning capacity.

Scientific research aside, if you’ve spent any time picking up women that you’ve just met, you’ll know first-hand the importance of fun and playfulness in getting the relationship off to a strong start. If you want to see this in action for yourself and how women respond to a fun and playful guy, try out this exercise:

The checkout tease

1.      Next time you’re buying something from the grocery store, pick a checkout that’s staffed with a girl that you’d like to flirt with.

2.      When you go to pay for your shopping, pay with cash.

3.      As you hand over your cash, when she reaches to grab it, don’t let go.

4.      When she looks at you, look her in the eye and give her a sweet smile. BOOM! That’s what a woman’s response to fun and playful flirting looks like, right there.

When you do this exercise yourself, you’ll see the power of fun in building an attractive and playful interaction with a woman. Now, let’s apply these same principles to becoming more fun and playful on your dates.

In this next section, I’ll walk you through, step by step, my favourite methods and techniques for having fun and being playful on dates.

Becoming more fun and playful on your first date

Your playfulness is something that you can work on RIGHT NOW and it will IMMEDIATELY improve your dating success. I’m going to share with you a simple set of things that me and my clients do on dates or when meeting women for the first time. I now do these things so much that they’ve just become second nature in the way that I interact with women. For simplicity sake, I’ll break down my approach into two areas so that I can explain it more easily to you:

  1. Playful conversation
  2. Playful touching

Playful conversation on a first date

Being playful in conversation is all about being silly, light-hearted and teasing in nature. It’s the exact opposite of taking the conversation too seriously or focusing too much on the facts, while ‘getting to know’ your date.

Here are a few of my favourite playful conversation techniques. Note: You don’t have to do all of these on a date as that may be going overboard. But be sure to try a few of these methods out and stick with the ones that suit your style and personality best.


Make a comment about her appearance, behavior or personality, which strikes the balance between being witty, entertaining and not too offensive. This can take a bit of practice and some girls will take a small bit of teasing better than others. If you’re new to teasing, practice on your male and female friends first before unleashing your wit on your date. Here’s an example to illustrate the kind of teasing comments that I typically say, “Wow, that joke was so bad that I even feel embarrassed for you right now. If you want to end the date and leave right now, I’d totally understand. I won’t even try to stop you.”

Role play

Describe you and your date in some fantastic situation which is entertaining, imaginative and possibly even throwing a joke or flirtatious tease in there too. For example, if she she likes music, maybe you’d say something like, “Hey, we should start a band, like the White Stripes and go on an all-American tour, playing a different state every night. You’ll probably have to brush up on your banjo-playing and Christian rock covers though.”


Make up a fun nickname for her, based on her attributes or something fun to tease her about – goody two shoes (If she seems straight laced), Woo-girl or Miss Naughty (if she likes to party), Tiny Dancer (if she’s small and likes dancing), etc.

Make up a spontaneous lie and have her believe you

Either in response to something she’s just said, or off-the-cuff, pick your moment and use your imagination to make up a small lie, on the spot.  Make sure to get her to (gullibly) believe you for a second and then call yourself out and maybe call her out for believing you.

It’s much easier and simpler than it sounds. Here’s an example to show you what I mean:

Her: [telling you a story of why she’s late] “…and then my car broke down…”

You: [you interrupt abruptly] “No way, my car just broke down earlier today too!

Her: [looks at you and pauses for a second trying to work out whether you’re lying] “No way, really?

You: “No, my car didn’t really break down. I was just trying to empathize with you. I have a nice and really reliable car.”

Ask her a question, and guess the answer

Ask her a question, but then use your imagination and sense of humour to suggest fun answers to the questions that you just asked, before she gets a chance to answer. For example:

You: “So what did you do last night? No, wait, don’t tell me, let me guess… You binged watched a full season of House of Cards in your pajamas with a bag of nachos and a tub of salted caramel ice cream.”

Repeat and reverse something that she’s just said.

The trick here is to repeat something that she references, making her the subject of the statement. The more obscure or childish this sounds, the better. Here’s a couple of examples.

Her: “That’s a smelly old garbage bin”
You: “You’re a smelly old garbage bin”
Her: “It’s cold, but still nice”
You: “You’re cold, but still nice”

Evade questions

Instead of answering a question that she asks you, just look at her in the eye and then blatantly change the subject, by asking her a totally unrelated question. Not answering a question shows that you don’t feel obliged to comply with the norms and that you live by your own rules. Besides, maintaining an air of mystery is sexy. Done right, it will make her feel even more attracted to you.

Have fun answers to common questions

On a first date there are a standard set of questions that you’ll get asked such as

What do you do for a living?

Have you always lived in [this town]? / What brought you here?

What do you do for fun / hobby / sports?

Instead of falling into the trap of giving her a boring answer to these questions (like 8 out of 10 other guys would), these predictable questions give you a great opportunity to impress her by having amusing or entertaining answers. Remember gents, hain

Here are a few fun examples that I share with my clients as alternative ways to describe what they do for work.

“I create art out of math, materials and physics” instead of “I’m an engineer”

“I argue for a living. Extremely well”  instead of “I’m a lawyer”

“I hypnotize clients with my cuff links PowerPoint slides and then convince them to let me tinker with their business” instead of “I’m a consultant

I build dreams out of spreadsheets” instead of “I’m an accountant

Playful touches and body language on a first date

When someone you like touches you, it’s an exciting sensation. It feels like little jolts of electricity and pleasure coursing through your body. You can use playful touching as a great way to amplify the attraction that she feels for you and to start building sexual tension. A word of warning, be sure that she feels attracted to you before you amp up the touching, otherwise you’ll actually repel her.

Here are a few of my favourite playful touches, but feel free to use your imagination and come up with your own, which match your personal style:

  • Give her a high five, fist bump or hand shake
  • Twirl her (most fun girls love being twirled)
  • Discipline her playfully by lightly punching her arm, shoving her away, gently slapping her hand or bum
  • Shove her into things (streetlights, garbage bins, hedges, etc.) as you’re walking down the street with her

Seriously, most guys don’t touch enough on the first date or even on the first few dates. They don’t realize that touching their date repeatedly, with escalating intensity, is the best way to get her body feeling physically comfortable and excited by you.

You generally want to start your touching early into the date so that it doesn’t feel awkward when you introduce it later on. The longer into the date or relationship that you wait before touching her, the more awkward and unnatural it will feel, and essentially the longer you’ll delay your first kiss, foreplay and sex.

Picking exciting things to do for a fun first date

In addition to being fun and playful on your dates, you can also amplify the attraction by doing fun and exciting things while you’re on your date. This is another tried, tested and proven way to build attraction more quickly, while making your date more enjoyable and memorable too.

Let’s riff on that idea a bit, which do you think makes for a more successful date?

1.       Having a three course meal at a fancy restaurant


2.      Riding a roller coaster and trying to shooting ducks at the funfair

I’ll give you a clue, one of the options has fun in the title…

OK, so unless you’re Gordon Ramsay, you’d guess right that option 2 makes for the more fun and successful date activity. What you might not know though is why it’s the better choice.

I’m gonna share that insight with you so that even if there’s no fun fair in your town, you can still pick fun dating activities that will achieve the same result.

Excitement amplifies attraction

Here’s an interesting biology/psychology fact that you might not know; when people are aroused or excited, they generally rate the attractiveness of potential partners higher.

This scientific finding was first uncovered over 40 years ago and since then it’s been tested in all kinds of ways. Feelings of attraction have been found to increase between two people who have:

  • Walked over a rickety bridge high up
  • Watched a scary movie
  • Ridden a roller coaster
  • Even just engage in physical exercise (meaning that your date activity doesn’t have to involve fear)

What this means when you apply it to your love life is that anything that gets your date’s heart racing is going to amplify the attraction that she feels for you.

The most prevailing explanation for this effect is that when your date feels excited, her physiological feelings of arousal (increased heart rate and metabolic hormone activity) gets misinterpreted (or ‘misattributed’ technically speaking) as increased feelings of attraction.

“Strong emotions are relabeled as sexual attraction whenever an acceptable object is present.”
– Arthur Aron, Intimate Relationship Psychologist


A point to note here though is that ‘an acceptable object needs to be present’ meaning that you need to have already built some degree of attraction with her in order for the exciting activity to amplify the attraction. Otherwise your date will feel like she is just riding a rollercoaster with some friendly guy.

Another great reason for doing fun activities on your dates is that the same principle applies to you too.  Meaning if you already feel a bit attracted to her, the excitement of your date will amplify the attraction that you feel. So by having exciting dates, you’re stacking the odds in favor of mutual attraction being built and a strong relationship being formed from the start.  If there was ever a killer argument to skip dinner and head to the funfair for your first date, this is it!

Best fun first date ideas

Now that you’re convinced that fun dates make the best dates, here are some of my favourite things to do that are WAY MORE engaging and stimulating than a traditional sit-down three-course meal.

  • Funfair, museum, zoo, aquarium, etc.
  • Go on a cool walk – do a pub crawl in a fun area, go check out a nice park or check out some architecture, visit a skate/bmx park, or walk along a place where there’s lots of high quality street art.
  • Do a fun activity – salsa dancing, skating, playing ping pong or pool, rock climbing.
  • If you have to eat, consider snacking instead of full-blown dining – go to a farmer’s market, grab a bite from a food truck or order finger foods in a bar.
  • Harness your inner child when planning your first date. If your planned date activity would keep your seven-year-old niece amused, then it’s probably a good choice.
  • When planning your first date harness your inner child.

Fun on a first date – Final Thoughts

You owe it to yourself, your date to have a fun first date. Fun dates are more memorable than boring dates and they are always a heck of a lot more successful too.

Being fun and playful with your date also makes you an inherently more attractive guy.

And adding excitement to your date amplifies the attraction that you’ll both feel, thereby stacking the odds in favor of getting the relationship off to a good start.

Looking for more great first date tips, here’s another insightful article focusing on fun first dates – The Ultimate Guide to First Dates – Part 1: Having Fun and Building Relationships.