Ultimate Second Date Guide: Tips, Conversation & What to Do

second date

Your first date went successfully.


But… don’t cheer too soon.

Because everything can still crash and burn during the second date…

So that’s why in this article, I’ll give you:

  • 5 Second date tips for guys, which will drive your partner crazy
  • 3 Ingredients for an epic second date
  • How to greet your partner on a second date
  • Top 10 good second date ideas by a dating coach
  • Second date questions which will make your conversations last forever
  • Going in for the kiss without being rejected
  • How you guarantee the third date
  • And what to do in case of bad weather & rain

By the way, have you seen my free Transformation Kit?

You'll get my best stuff absolutely free: 12 Opening lines that actually work, my 5 best texting tips (including copy-paste lines for Tinder), and the Friendzone Houdini. Download the Transformation Kit here.

Let’s start.

Second date etiquette: A NON-awkward greeting

Let’s get your second date going with a running start.

This is already done at the greeting.

The greeting for your second date is crucial.

Before you make a fool of yourself.

Because there are tons of options:

  • Just saying “hi”
  • Shaking hands
  • One kiss on the cheek
  • 2 kisses on the cheek
  • 3 kisses on the cheek
  • Hug
  • An extensive make-out session

What you want to avoid is that your date wants to kiss you, and you go for the handshake…

Or that you go for 2 kisses, and the other for 1…

Or that you open your arms for a hug, and that the other doesn’t like it…


Don’t worry, I’ll give you solutions.

If you’ve already kissed:

Hug, but don’t kiss right away. That can come later.

If the other doesn’t love physical contact (which you may have noticed on the first date), then just say right before the meeting ‘one kiss’ and kiss on the cheek.

(Or whatever other number you like.)


A big fat don’t. Whatever you do… don’t shake hands. That’s a way too official way to start your romantic evening. Don’t.

Tip #1: The 3 ingredients for a successful 2nd date

Do you know the feeling?

After two dates, you suddenly get radio silence from the other party.

On your first date, the sparks flew. You had an amazing time together.

Soon the second date was on the agenda. You counted down the days.

But after the second date…









Dead silence.






“WTF”? How?”

I’ll give you clarity:

Think of your dates as a TV series.

Episode after episode, the story builds up to a climax.

You want to do this same buildup on your consecutive dates with the same person.

But, as you know, series sometimes flop on the second episode.


The pilot (the first episode) made your mouth water for the sequel. All the storylines and characters that were introduced almost made you tinker together a time machine to quickly skip the working week to the next episode.

And then you see that second episode. What a disappointment. It doesn’t at all live up to the expectations that were created in the pilot.

The same reason is why dates are often stranded at number 2.

What often goes wrong on second dates is that the pilot, the first date, exceeds all expectations. But the second episode, your second date, doesn’t match the level that has been achieved in the pilot.

Why dates often end at number 2?

Second date expectations are usually not met.

For example:

  • Just drinks in a boring brown pub, again
  • You guys don’t get to know each other any better because no new or deeper topics are touched on
  • There’s no attempt to build to a climax

In short, you just repeat the first date. And if ‘repetition’ is the subject of the series, then you stop watching after two episodes.

Repetition is rarely exciting.

Now maybe you think:

“So I should just make my first dates more boring?”

Haha, creative thought, but very ineffective. By doing this, you only make sure that there are fewer second dates at all.

It’s better to take care of unexpected twists and turns in the second episode and subsequent episodes. Get the other person excited, so they always wonder what’s up next.

With every good film or series, you know that they are full of surprises.

We will use these plot-twists to provide your dates with a dose of excitement.

Namely in the following 3 ways:

Ingredient #1: Date-chat for 2nd date professionals

Have you ever experienced where after two great dates the other one quits anyway? And you have no idea why?

We’re ending that now. So that date #3 doesn’t remain an incident, but a given.

Let’s go back to those first two dates:

Your first date was full of roaring laughter. You had a great time together.

The second date was added to the diary very soon.

Once again, you have a good time.

But still the other one dropped the bomb after date #2:

“I had a great time with you. You’re a nice person. But the spark is missing, so I want to leave it at that. Sorry.”

You look at your screen with glassy eyes:

“You had a great time…

…I’m a nice person…

…but the SPARK is missing?”


If you have experienced this.

Then pay attention!

Even if you haven’t, stick with me. Because this is going to give you the first twist you can add to your dating script.

That first date must have been a fun time. Otherwise, it’s impressive that you even arranged a second date.

But often that first date will also be a tiny bit superficial. You’re just getting to know each other.

Through the combination of entertainment and interest, and from time to time a flirty spike, this date makes the other curious for more.

If, however, you repeat this on your second date… that’s boring, and that’s why you drop out. Because just like a TV hit series, you want twists and turns.

More importantly.

Staying in this investigative mode does not create a real connection between you.

That missing connection is what the other person means by ‘no spark’.

You do entertain the other on the date. But you don’t connect and make her feel something about you.

During the date, that entertainment is fun. A quick high. Yet this peak quickly fades to emptiness afterward, and then there’s nothing to rev up to the sequel.

Now you don’t have to reinvent the wheel completely. But we are going to add a plot twist to your date.

Instead of just laughing on your date, we’re going to add a much-needed connection.

So, what to talk about on a second date?

  • Tell more personal stories, where you show vulnerability.
  • Ask questions to find out the motivation behind the other person’s choices, rather than just the facts.
  • Instead of ‘me’ and ‘you’ as the subject of your conversations, go more in the direction of ‘we’. What are you going to experience together?

Get to know each other on a different level.

(By the way, Tip 5 is going to help you with deeper conversation topics later on.)

In this way, you will shed light on other aspects of each other’s personality and you will stay on the edge of your seats out of interest.

If you don’t think this is right for you, then it’s also possible that a lack of masculinity played a role. This is a broader concept, so open the article about what masculinity and alpha behavior mean now:

>> 7 Ways to Get a More Masculine Edge (to Balance the Feminine)

Ingredient #2: Date spots on steroids

Time to connect your second date to a speed IV.

Because your date location also needs a twist!

Do you think your date is all about you and her? That the environment doesn’t add or subtract anything to the date?

If so, I’m gonna bring about a mind shift for you.

Cause you’re going to add a big tablespoon of personality through your date location.

The other person will not only get to know you through what you do and discuss with each other during the date, but also through where you are going.

This way, your date will see multiple angles of you, and you will appear to be a more versatile person.

Now I don’t know what your personality is. But I choose, for example, the informal living room atmosphere for my date spots. All that formal fancy stuff on dates, it’s not for me. And that’s what I communicate to her through my choice of location.

Going the fancy route makes your date feel… at least for me, like an official date.

One of the elementary pearls of wisdom I learned early on:

“A good date doesn’t feel like a date.”
– Buddha

Or maybe I said this myself, I frequently confuse myself with other historical giants.

Anyway. I’ll give you a list of date ideas later. From this, you can get a lot of inspiration and figure out which activity suits you best.

This way you can make sure you will meet your second date expectations

Ingredient #3: Second date kiss

Going for the kiss… feels difficult.

Luckily, I have a smart solution to this problem.

Because let me guess… you’re thinking one of the following things when you’re planning to kiss her:

  • Does she even find me attractive?
  • What is she going to think if I kiss her?
  • What if I try to kiss her and she turns away? That’s super awkward…
  • She hasn’t given enough signals that she’d like to be kissed
  • Oh no, what if I metoo her? I’m not that kind of person
  • Is this the right place? Should I wait longer? I don’t want it to seem rushed…

Your thoughts run wild, and it gets worse and worse.

While in reality, it’s just a simple bridging of the distance between your heads, in your head, it looks like you’re deciphering the Enigma code.

All these thoughts basically mean your thoughts have the wrong starting point. And they’re going to lead to many more rejections.

You’re going to cause problems for yourself – which will lead to long-time singlehood.

Especially on the second date, you want to adopt a completely different mindset.

You probably think now:

“She’ll ONLY like me if I have ‘x strategy’, ‘y sense’ and ‘z touch’”

While the attitude you want is:

“She likes me, until I can tell she doesn’t”

This means you can feel a lot more relaxed about dating. You can be in the moment, and enjoy being with each other. And experience many more love adventures.

Easier said than done, I know.

But trust me.

It’s a combination of doing and experiencing. And adjusting your mindset.

When during date one, you only hugged or held hands (or maybe didn’t have any physical contact at all!), it’s extra important to get your lips into play this time around.

Because if someone goes on date 2 with you, you can assume that person would love a kiss.

You’re probably wondering:

“Can I kiss her now? Is this the moment?”

We like to wait for signals from the other person. We really, really don’t want to be stranded with our lips on the other person’s cheek, for example.

Pro tip:

But how do you go about kissing the right way? This is a broader topic, so I figured it deserved a full article:

>> 7 Kissing Tips and Techniques to Become an Amazing Kisser

If you don’t go for the kiss, the only thing the other person thinks is the following:

“He/she doesn’t like me very much after all it seems”

The other often has a completely different idea than you think. And this is just one of the examples that shows your brain is playing tricks on you.

What you think is false 9 out of 10 times.

By believing in those thoughts, your love adventure ends prematurely more often than not. And you are alone again.

When there is no need for that.

It’s a shame.


When you’ve poured the above 3 parts into a date-winning cocktail, there’s no reason for you not to score a third date.

I’ll also provide you with some more tips to get that third date in your diary – but that comes later.

Because first, we enter the Walhalla of date ideas together.

Namely a list that gives you all sorts of exciting possibilities, for your second date.

Good second date ideas

You’ve had your first date, but what to do on numero dos?

Maybe you feel like you’ve used up all your ideas for the first date… And now you’re worrying:

“How am I going to make this one exciting?”

If you worry about this – and even if you don’t – then take a moment and think back to the first date.

That should help you get some inspiration.

Because I can promise you: I’m sure you two discussed hobbies and interests.

So maybe go do something with those interests for the second date. See if there’s something both of you like, or combine two things to create something that will appeal to both of you.

But remember:

Just like with a TV series, it’s the actors who make or break the episode.

It doesn’t matter if the location was perfect. If the acting is worse than the average sixth-grade musical, it’s still a shit film.

The characters are the most important. The location is the icing on the cake.

That icing on the cake can be found in the list of fun second date ideas:

Idea #1: Arcade hall

Competition is always exciting. But not just that: competition also has a very attractive advantage…

According to research, the sweaty smell of exciting (which competition helps release) makes you more attractive.

So take your date to an arcade hall.

Challenge each other to a game of air hockey, whack-a-mole, racing, shooting zombies or a dance-off.

And see who’s king or queen of games.

Pro tip:

Bring about extra exciting in the following way:

Make a bet: The loser has to pay for drinks in the cafe you’ll go to afterward.

This excitement will help with bonding, and also checks if you trust each other.

Idea #2: Captain of your own ship

Nothing is more exciting than sharing a boat on the quiet water.

Go somewhere where you won’t run into other people.

This means you can spend some time in a “bubble” together.

It’s just the two of you, and you can’t easily leave, because you’re surrounded by water.

Of course, don’t forget to splash each other.

Idea #3: Psychedelic golfing

Tripping without drugs?

Go glow golfing.

Play a game of midget golf together while everything, from ball to golf club, flashes by in bright neon colors.

Idea #4: Climbing a church tower

You know what’ll happen, high up in the church tower.


(Yes, you have to kiss her on top of the church tower)

The location makes things extra exciting. And when the kiss comes, this gives you an extra romantic feeling.

You can climb church towers throughout the country. Many churches allow this, so check if there’s one in your area.

Idea #5: Get to know each other thoroughly

Important about the second date is that you have to get to know each other better.

You want to mix superficial subjects with deeper topics.

You can do this by asking each other more intimate questions.

Use the 36 love questions of psychologist A. Aron to fall in love with each other.

I’ll also soon give you ten more questions for future dates. And some conversational topics that delve beneath the surface.

Idea #6: Nightly walk

Walking together is fantastic.

It allows you to get to know each other, and the whole date doesn’t take place in one location.

It’s an ongoing adventure.

To make this adventure extra exciting, you should take this walk at night.

Really late, so you don’t run into anyone.

Every sound you hear in the middle of the night – and which you can’t see! – will make you tremble.


You’re there to protect your date, aren’t you?

Idea #7: Discover a new city

Discovering a new city together is like traveling together.

Discover the best cafe in the city and have a drink.

Discover the city on a tandem. I mean… why not?

Nice spots to discover in an unknown city include:

  • The harbor
  • The park
  • Downtown

And when you arrive in the park, you grab the picnic basket from idea 8.

Idea #8: Love goes through the stomach… in small bites

A wonderfully relaxing date with a great aftertaste.

Take a blanket, fill the basket with food and drink (including wine!), find a spot in the park near a tree, and go for a picnic.

Yes, especially that tree. That tree is important.

How to dress up your date further:

  • Go to the supermarket together in advance and buy what you both like. Choose things for each other, too. Bonus points if you can also make her bring all sorts of things from home, without telling her it’s for a picnic.
  • Picnicking is a relaxing date. There’s not a lot of pressure, because you’re constantly making and eating the food.
  • As I said, go picnic near a tree. You can sit against the tree and create a romantic moment. Sit her down between your legs. Massage anyone?

Idea #9: Ice skating

Is your second date in winter or autumn?

If global warming permits… go skating together!

Walk to the skating rink in your area, and there’s your whole date!

Jump onto the ice and skate laps together.

Extra fun if neither of you is any good at it.

Then drink some hot chocolate or mulled wine together.

And try to skate hand in hand, too. That will increase the chance you’ll fall 😉

Idea #10: Stay-at-home date

I know what you’re thinking.

A stay-at-home date sounds really fun and clever.

After all, your bedroom is just around the corner.

And it’s not that weird to end up there on a second date.

Still, organizing a stay-at-home date is like defusing a bomb.

By cutting the wrong wire or skipping a few small details, the bomb will explode, and you turn from flirt to creep.

You want to avoid that, of course.

How, you say?

Read this article to find out:

>> How to ‘Netflix and Chill’ Date Without Being Creepy or Awkward

What should be clear after these date activities:

Avoid that the second date turns into ‘more of the same’.

It’s okay to go grab a wine somewhere, but avoid repeating yourself. It’s going to start looking like the umpteenth Tinder date.

Grabbing drinks is fine. That’s my go-to idea too. But then make it original.

The cafe on the corner? No thanks.

Bonus: What to talk about on a second date

Where most people get stuck is the conversation during the date…

Men, as well as women, email me about this.


That’s why I made the Conversation Cheatsheet, featuring the best tips for smooth chats, flirty talk, and other goodies.

Download here for free.

Tip #2: How to ask for a second date

I’m going to prevent you from missing out on the second date.

When your first date went well, there’s little chance that she doesn’t want to see you again.

Pro Tip:

Plan your second date for under 10 days after the first one.

This helps you keep social momentum.

Because otherwise, you’ll slowly forget one another.

Sometimes you’re both just busy, and then you have to be patient.

Then it’s handy to send fun, flirty messages.

Download my Texting Cheatsheet full of tips, phrases, and ways to send fun messages here.

But while waiting for your second date, you can make a few huge mistakes:

  • Inundating her with messages, that it was heavenly to be with her and you long to see her again
  • Insisting on a new date, when she’s temporarily busy
  • Going way too fast after the first date (think relationship stuff). No bro, you’re virtually strangers. A relationship is still far off.

In short, this is going to make you seem incredibly needy.

It’s often your brain that plays crazy tricks on you.

Or you think you’ve won her after one date. That’s going to make things feel too easy. Or you’re going to be afraid of losing her. So you try to do whatever you can to prevent this.

But the very opposite will happen.

After the first date, you don’t want to act differently than before the first date via chat:

  • Send her a suitable message the next day. For example: “I had a great time with you yesterday, [Name]” (Add a little joke for bonus points)
  • You then want to keep teasing, exciting and amusing her over chat
  • Chat with her from time to time. Sometimes with a little break, sometimes a bit more frequently.
  • Keep the momentum of the date via chat (I’ll tell you how to do this!)
  • Believe that she likes you even more after the first date unless you can see proof to the contrary

“Quietly but surely you make your way to the second date.”
– Your mantra on the road to date 2.

I said “quietly”, not “slowly”.

Because it’s also a mistake to be too slow.

When you go too slowly, she’ll lose interest. She’ll assume you don’t like her.

When you go too slowly, she’s going to stop investing in the relationship. And soon, you’ll start your search for a girlfriend from square one again.


But okay. There are some things you can do in order to make a second date inevitable.

Pro Tip:

It’s handy to get some inspiration, for example with cool example phrases for your date.

Would you like a handful of readymade phrases for all your chats?

Download them here for free.

Tip #3: Clever trick to fill the time on chat between your dates

Do you find it tricky to keep your chat going in between dates?

This tip will give you a way to keep the momentum going.

Chatting in between dates is a must. Otherwise, she’ll assume you forgot her, and it’s going to get hard to plan a sequel.

So you want to keep up the date momentum in your chats.

But how do you do that?

You probably know all those people who take selfies in places they visited.

That’s their way to remember where they’ve been. It makes it easier to relive that time!

You want to use this principle for your dates, too.

But don’t take a selfie by yourself.

Take a together-selfie.

A togetherie!

That way, you can remind her of the date.

This will reintroduce the momentum in your chat, and it’ll make it easier to continue the conversation.

Such a selfie is by far the easiest way to keep your conversation going.

And make her look forward to your next date.

But always keep in mind the next tip, when you’re chatting:

Tip #4: Pretend it’s your first date

Avoid this trap so your date adventure with her doesn’t end with the second date.

Where a lot of men screw up is when they slouch too much at the second date.

They think, because the first date was successful, they’ve got her in the pocket.

But that’s not at all true.

You want her to see a different, positive side of you.

For example, through those plot twists I mentioned earlier.

This will make her more and more curious about what else there is to discover about you.

Pro Tip:

Here’s some second date advice for you.

Keep her curious – be like an onion being peeled. Show her a different layer every time.

Further and closer until she finds your core.

Of course, your lazy side is also a part of you, but that’s not going to make you look good to her!

Tackle your second date like it’s the first.

That means:

  • Appear as your best self
    Clothes, hygiene, you name it.
  • Did you kiss on the first date?
    That doesn’t mean you jump all over her immediately when you greet her. A warm hug is a good starting point. However, the fact that you’ve already kissed means you should kiss her again during the second date, and take it a little further.
  • Organize another original date
    Check the list + bonus video to get inspiration.
  • Make sure to prepare properly
    Check your chat. Revisit the topics from the first date. Ask what she’s been up to in the meantime.

A small side note about the first one:

So yeah, clothes and hygiene are equally important.

Now, I’m not going to teach how to take a shower. But I can give you some tips on how to dress properly.

Get them in this article:

>> 10 Tips – Dress to Impress for Men (Ladies LOVE This)

Flashback to what I said earlier:

“If she goes on a second date with you, she likes you! The door is open. You just have to walk through.”

At the same time, I said it’s good if the conversation goes a bit deeper on the second date.

That’s why I’ve prepared a few exciting conversational topics for you in the next tip.

Tip #5: Second date questions

Don’t let the second date be the end, by doing the following:

“Delve deeper and deeper with your questions and topics.”

Make your questions and topics more personal and intimate.

To accomplish this, I’ll give you 10 questions you can use on your second date.

Here are the questions:

1. Which person you’ve met has changed you the most?

2. What are you up to lately? Why?

3. If you were to start a company, what kind of company would it be?

4. If you could change one thing in the world, which wouldn’t just be good for you, what would you change?

5. What’s something you tried once, but never want to do again?

6. If you were a man for a day, what would you do?

7. Would you prefer to live 10x a hundred years, or 1x a thousand years?

8. How do you flirt with men?

9. Where would you touch me the first if I was naked in front of you?

10. What’s your secret trick to excite a man?

You’re almost in winner mode for your second date.

 But Dan, 10 questions is not enough! I want more examples. 

More, you say? What about 131 examples, would that be enough?

Wish granted. Get them here:

>> The 131 Least Boring Questions Ever to Ask Your Date

But before you leave for the second date, check the trick in the next tip.

This will dot the i in “winner”!

The trick to pimp your second date

Of course, I could tell you way more about the second date:

  • How to approach the date
  • Fun phrases to say, to keep your interactions exciting
  • Or text messages to send to meet up at your house

But so you don’t have to read all that, I’ll show you instead.

This way you will go far beyond the second date expectations.

You can find all that info in my free Transformation Kit.

I don’t just discuss dates, but also how to meet and seduce women. In-person and online.

Download it right here, it’s free! 

Your bro,
Dan de Ram

Stop awkward conversations
and painful rejections

My free Transformation Kit will make you irresistible to women.

  • 12 Opening Lines that Actually Work
  • 5 Date Generating Texting Tips (Plus Copy-Paste Lines for Tinder)
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