How to have the best first date, every time

This is one of the most common questions that I get asked as a dating coach.

A date can be a pretty awkward and nerve-racking affair, especially if you don’t know what you’re doing.  And first dates are even more awkward, because you’re on a date with someone you barely know and having to make a first impression at the same time. And, there’s the added pressure that if you don’t come across well, there won’t be a second date.

So to help answer the question of how to have the best first date, I’ve pulled together my most valuable articles and posts on this topic.

These resources will help steer you in the right direction and make your first dates a LOT MORE fun, exciting and successful. They’ll also save you from a lot of wasted time, and reduce your chances and frustrations from having dates go sour and not knowing why.

1.   Unlearn the bad dating advice which might be holding you back

Crap dating advice is EVERYWHERE and what’s worse, some of it can do more harm than good to your love life too.

For many years I’d personally suffered from the (mis)belief that when you’re on a date, you should ‘just be yourself’ and that the whole point of going on a date was to ‘get to know someone’.

I’m sure you’ve heard this type of conventional dating wisdom before and although on the surface, it sounds sensible, following this advice too closely will screw up your dates rather than make them a success. Starting now you need to ‘unlearn’ the bad advice and replace it with more helpful and useful insight. Here are a couple of articles which will help the unlearning begin:


2. Learn and apply some surefire first date strategies

Have fun and build attraction

The fundamental dating strategy that we recommend in DateSchool is to build fun and attraction into your dates, especially your first dates when starting a new relationship. We even state this principle as the DateSchool first date success formula:

Fun + Attraction = 2nd Date


The following articles will help you get into the habit of having fun and building attraction on all of your dates, so that they’re more enjoyable, memorable, and ultimately more SUCCESSFUL.


Build a deep connection with your date by asking awesome questions

Connection is that feeling of true companionship that we look for in our soulmates. Unlike Attraction, which is mostly driven by immediate primal and physical urges, connection is a warm sense of friendship and companionship that’s deeply psychological in nature.

Building a connection is about spending time talking with her so that she feels like she really knows you, understands you and can begin to trust you. This is a key to kick ass dates. Key.

You build connection with your date through deep conversation and by making an undistracted effort to genuinely get to know her for the person she really is.  You really want to understand what she's all about. What motivates her? What's unique about her outlook What principles does she stand for and why?

“All a girl really wants is for a guy to prove to her that they are not all the same.”
– Marilyn Monroe

Instead of dorkily asking about her values, principles and beliefs outright (because these are tough questions for anyone to answer and it would seem awkward and unnatural), it's more fun and more helpful to ask her fun and specific questions.  For example, here are five of my all-time favourite first date questions.

My top-5 first date questions:

  • What’s the favourite thing that you own and why?
  • Who’s your best friend – what makes them special?
  • What’s the kindest thing that you’ve ever done for someone else?
  • What’s the most embarrassing thing that’s happened to you this year?
  • If you were going to take me away for the weekend, where would we go?

Using deep questions like this to build connection is common practice among daters who have their shit together. Studies have even shown that asking and answering deeply personal questions is a short-cut to building deep and powerful connection quickly.  One study in the US showed that by asking each other a specific list of questions for 45 mins, couples who had never met before became closely bonded.  Even two months after the experiment, about a third of these couples had hung out and/or sat next to each other in class afterwards!

If you want to know the actual questions that were used in the experiment described above, I’ve pulled them together with some instructions for you in this one helpful PDF, which you can save in your phone, so that it’s nice and handy for your next date.  Just enter your info below and we'll send it your way.

3. Design and run an EPIC first date

As your dating experience grows, you'll appreciate the value in planning dates that help you bond more deeply and seduce more quickly, by design.

This is a slightly more intermediate or advanced dating strategies, because you want to get the hang of having fun and building attraction first, to the point where it becomes second nature. Once you've nailed that, you can start honing your connection and seduction skills.

A lot of the time, you'll find that the surroundings and the logistics of your date make it easier to have fun, build attraction and create a deep connection with your partner.  So it helps to build the right atmosphere and privacy considerations into your dating planning.

To illustrate the date design process with example of how to string actual date plans together, here are a few of my date ideas and activities in London, one of my favourite cities to date in – more date plans for other cities coming soon!

Final thoughts on crushing first dates

When you know what you’re doing, first dates can be loads of fun.  And frankly, they should be – for your sake and hers.

It’s very empowering to be the one that’s most comfortable, least nervous, and therefore able to take the lead and help your date relax. Smart daters aim to be a relaxing and calming influence on the date, by knowing what to expect on a date, knowing what to do to be successful and by planning accordingly in advance.

Now get out there, have as many first dates as you can, enjoy the ride, and learn all you can from it!