Ultimate Guide to Dating Part 2 – Planning Kick-Ass Dates

Failing to Plan Your Date Equals Planning to Fail

In the previous article, I introduced the purpose of dating as an exercise in having fun and learning how to develop and then build the core relationship pillars: Attraction, Connection and Sexual Intimacy.  Now it’s time to build legendary dates.

In this article, which is the second part in the Ultimate Guide to Dating series, we’ll cover how to plan and run your dates to help you bond with your date and build the three relationship pillars most quickly and effectively.

Why bother planning your dates?

When it comes to planning dates, a question I’m often asked is:

“Why do I need to care about planning my date?” or, “Can’t I just meet her for a coffee and then take it from there?”

To which I answer, yes you can just meet her for a coffee and wing it from there…

BUT A well-planned date will make the date a much simpler, easier, and more enjoyable experience for you both.

Don’t believe me? There are at least half a dozen compelling reasons why planning a date is a smarter move than leaving it to chance:

1.      A well planned date helps you to relax

When you’re on a date, you’ve already got enough to think about, you don’t want to get pre-occupied with thoughts like ‘How can I get her someplace quiet, where I can make a move?’ or ‘I want to kiss her, but it would be totally awkward to reach across the table to do it.’ Having your relationship building pillars in line, and your date locations (there should be more than one spot you hit up on a date) planned out in advance will help you to stay in the moment with your date. Being prepared will also give you the comfort that you already have an ace or two up your sleeve for when you want to turn up the heat with her and go somewhere a bit more private.

2.      Having a familiar date plan makes you more confident

Once you have a good date plan and you repeat it with different women, you’ll grow increasingly more familiar with your surroundings until the point where you barely notice them.  The net effect of this is that it will make you seem more comfortable and confident on your date. You’ll appear more relaxed, less nervous and ultimately more attractive.

3.      Exciting dates make her feel more attracted to you

Doing fun and exciting things on your date will raise her heart rate and actually amplify the attraction that she feels towards you.  This is an attraction hack.

4.      A well-planned date makes deep connection and sex more likely

Deeply connecting with your date and seducing her effectively requires some degree of privacy and isolation from the world around you. Ideal connection and seduction spots are not always that easy to stumble across without forethought, especially on a busy night in a big city. Having a connection/seduction location already on your date plan can make all the difference between getting lucky or going home alone.

5.      Planning keeps costs low

If you’re a baller on a budget, then insiders knowledge of the inexpensive date options around you is invaluable.  What’s more, the more cost effective your date plan, the more dates that you can afford to go on each week and month. Sweet!

6.      Well-planned dates are more memorable

When done well, your dates will become the stuff of legends. Your legend. The story of how you and your girlfriend / wife / life partner first hit it off should be a great one. At dinner parties for years to come, the stories of your first dates will be told and re-told, so why not make those stories worth telling again and again?

The reality of relationship-building is that quite a lot of things need to happen within your first few interactions. And it’s not easy to make all of these happen within the first few dates while the clock is ticking, particularly if you’re nervous and especially if you’re not well-practiced at dating.

Within your first 10 hours together, you ideally need to:

·         Make an attractive first impression

·         Relax, have fun and enjoy each others’ company

·         Talk deeply and try to get to know each other, at least a little bit

·         Flirt, hold hands and build sexual tension

·         Kiss and begin your seduction

Without a bit of forward planning, it’s pretty hard to make these things happen in sequence and seamlessly.

This is one of the main reasons why so many guys and girls nowadays have a hard time dating.  Not only are so many guys and girls unaware of the steps required when relationship building, but they also under-appreciate the atmosphere and logistics that are required for fun, attraction, connection and sexual intimacy to take hold and grow in sequence.

I suspect that many daters mislabel their limited understanding of dating as being unable to find their perfect match.  How many potential dating successes might have already passed you by?

Well designed dates get the results they deserve.

How to design kick ass dates

So now that you’re convinced of the value of planning your dates, you’re probably wondering, how exactly do I go about it?

There are two main design considerations that go into my date plan:

1.      Which relationship pillar(s) do I need to build on this date?

If I’m looking to build initial attraction, then my date plan will be different in this instance than a date where seduction is the main focus. In practice, this means that my first dates have a deliberately different design to my fourth or fifth dates in a relationship.

2.      What options are available and appropriate at that time of day or night?

Cafés, bars and nightclubs all have different opening hours, so be mindful that the time and day of your date will impact date options available to you. My favourite date plans always include shops, bars and restaurants with long and late opening times, so that I can always fall back on them any time of the week or weekend, and either during the day or at night.

Designing a date to build relationship pillars

Plan to build and amplify attraction 

Building initial attraction involves demonstrating attractive aspects of your presence, personality, social status and sexual attitude in a very short time.  It’s all about creating an attractive first impression. You will read more about how to do this in this article, but if you really need to bulk up your natural attractiveness, check out our masterclass focused solely on this topic – there’s nothing else like it.

Generally speaking, you can build initial attraction anywhere, because most of your initial attraction building will come from your body language and the words that leave your mouth.

You can however AMPLIFY attraction through clever date planning.  This is a smart dating hack that can help move things along nicely and accelerate your bonding.  The principle at play here is that certain aspects of a date can help to demonstrate or emphasize your naturally attractive qualities. Let’s bring this to life with some examples.

Go places that you know the staff

By taking your date to places where you know the doorman, bartender, waiting staff, chef etc, you are building your social status in her eyes.  I always like to take first dates to places where I’m somewhat known, it’s like having a friend do a quick cameo on your date to affirm that you’re a good guy. For an extreme example of this principle in action, check out this iconic scene from Goodfellas and Karen and Henry’s first date.


Involve friends

A lot of guys have some weird resistance about having their dates meet their friends, but personally I prefer to have this happen and often, as early into a relationship as possible.  My friends are the full package – smart, socially intuitive, well learned and kind, so by association these values reflect well on me.

You can even achieve a result by involving her friends. When I first meet a new date’s friends, I go on an immediate charm offensive. I like to quickly and indirectly demonstrate my attractive qualities and then try to really get to know them well too (build connection) in the short time I have. That way I know that when my date invariably asks her friends afterward, “Hey, what did you think of him?” I can anticipate a glowing review and that’s social proof from a trusted source as far as my date is concerned.

Go places that you know a lot about

Think about the situation for a moment where:

  • You’re dating a girl who’s new in town and you’re showing her the sites and giving her the insiders’ guide to your city.
  • You’ve taken your date to a bustling food market and you’re giving her a whistlestop tour of the best and most hidden stalls.
  • You’ve taken your date to a restaurant with a bafflingly lengthy or foreign and ultimately confusing menu and you take the lead and order an amazing selection of food for both of you.
    All of these examples are instances of you hosting and taking responsibility for her in some way.  These small demonstrations subtly tell her that you’re capable of taking the lead, taking responsibility and protecting her. This is a subtle but very powerful way of showing a highly attractive alpha trait that really separates the men from the boys.  It shows your date that she’s a guest in your world.
“Girls rather hear a guy say” I’ve made plans for us” instead of the usual “I don’t know, whatever you want to do”


Have fun

Having fun together is HUGELY important when you’re dating, especially if it’s your first date. To put it bluntly, if she didn’t have enough fun on your first date, there won’t be a second date.

Also, the more fun she has with you, the more attractive she’ll rate you. Remember, fun amplifies attraction.  If you want to learn how to build more fun into your dates check out this great foundational article on the topic.

Plan to connect with her

Establishing a strong connection with her should be an important element in your date plan, if it isn’t already.

You’ll build this connection through deep conversation so that she feels like she really knows you, understands you and can begin to trust you.

This means that your date plan needs to feature a location, the right atmosphere and enough time for the two of you to have an undistracted, uninterrupted and ideally isolated bonding session, far from everyone else.

My favorite connection locations in order of awesomeness are:

1.      A fireside 2-seater couch in an olde style pub

2.      My living room couch

3.      A quiet corner in a cocktail / wine bar

4.      A seat on a park bench

5.      A walk together, when and where it’s not so busy

6.      Having a private meal or coffee together sitting side by side

A great little connection building hack is to hit multiple locations in a short amount of time during your date.  The technique of ‘bouncing’ frequently is well known and well-practiced in the seduction community.

You’ll find that when you go to two or three different locations during a two-hour date, you’ll build a lot more connection than if you just stay in the same place with a woman for two hours.

Most guys in the know conclude that by seeing you in a few different contexts in rapid succession, women seem to build a sense of familiarity with you more quickly.  It’s as if it becomes easier for them to see themselves being with you.

Plan to Seduce Her

Successful seduction is as much about planning as it is about making the right moves with her.  Let me show you what I mean.

I often teach guys that your seduction efforts are 10 times more likely to be successful if you’ve accounted for the 3 P’s: Proximity, Privacy and Possibility.


It might seem like common sense, but the most common roadblock that budding seducers hit is that their date is not physically close enough to them to touch freely and non-awkwardly. You need to be near or directly next to each other, in order to seduce effectively.


The watchful gazes of other people around you will hamper your seduction.  Ideally you want to be somewhere completely isolated, or somewhere that you can both get lost in the crowd and be completely anonymous.


Refers to the likelihood of foreplay or sex actually happening for you. Ask yourself,  are the location, logistics, and timing all conducive to getting it on? Are her friends going to let you borrow her for the night? Is there enough time between now and work the next day?

As you get better at dating and if you’re so inclined, be ready for same-night sex, even on the first date or even on the night that you first meet.

So PLEASE include a location in your date plan where you can sit next to each other, and touch and kiss freely, as a prelude to sex. Ideally this location is somewhere dark and private, where you won’t be disturbed.

A quiet booth in a bar or club, or the back seat of a taxi are ideal spots to consider. Definitely don’t land somewhere brightly lit or too public, like a packed subway carriage with the stares, sounds and smells of other people around you – that’s a romance killer, right there.

Design your dates around relationship building


The main idea here is to plan your date so that your surroundings are advantageous to quickly building attraction, connection and sexual intimacy with your date.  Different locations built into your dates will be more conducive to building each relationship pillar – so you want to plan for that accordingly.

Once you’ve identified a few perfect locations and incorporated them into your typical date plan, then you won’t have to think about it again, which frees your head up to focus on enjoying yourself and the beauty in front of you.

Common dating activities

When you’re planning your dates, in addition to the locations, you’ll want to give some thought to the activities too. The most common dating activities are eating and drinking, or going out to see or do something fun, depending on what’s available to you and what time of day or night it is.

Here are a few thoughts on how to make these typical date activities work for you and not against you while you’re building a relationship with your date.

Drink something

Whether it’s caffeinated, alcoholic or carbonated, having a drink together is a great way to start your date and hands-down the most common first date, for good reason.


I always recommend that if you’re new to dating, having an alcoholic drink or two on your first date will help relax you both and will help the attraction to grow naturally.  There’s some science behind this too, alcohol actually makes people view others as being more attractive – beer goggles are a real thing folks!


Coffee dates are also a smart first date option, because they can happen any time of day and are a lower investment and less threatening first date.  But be warned, the stimulating nature of caffeine can also heighten and amplify any latent nerves or anxiety that you might be feeling, so I always recommend café dates as being better suited for more experienced and confident daters.

Eat something

Your date might arrive hungry or your date might end up going on so long that you both need to eat something, so it’s always helpful include a food option in your date plan.

I’d recommend a quick bite over a small two or three course meal, at least in the early dates.

With a long meal, you’re sat in one position too long and there’s too much pressure to try and keep the conversation going in a stagnant environment.  When you’re up and moving, you’re more stimulated and conversation flows more freely.

So aim for appetizers, sharing plates, finger foods or snacks from a food truck or market stall.  They’ll keep you and your interaction light and energized.

See or do something fun

When your date is genuinely having fun with you, she’ll actually perceive you as being more attractive. This is a genius attraction hack and worth repeating with the purpose of designing your dates to include more fun elements.

Until you learn enough about your date’s interests and hobbies, it’s ok (in fact it’s a good thing) to suggest doing fun things together based on your own interests and recommendations.

Here are a few tips for picking suitable and fun dating activities:

Avoid stagnation

For a first or second date (until you’re ready to build sexual intimacy), avoid doing anything that forces you to sit next to each other without talking for 30+ minutes.  Things will just get awkward otherwise.  This means no movie or theatre shows until you know each other better.

Do something competitive

I’ve a taste for over-achieving and driven women, so I always like to introduce an element of competitiveness in my dates. I love doing things like playing pool, board games, bowling, table-tennis, air hockey and arcade games.

Do something exhilarating

Research shows that anything that gets her heart pumping will amplify the attraction that she feels towards you.  This counts for physical activities or even scary movies.  So consider the following activities for your dates: ice-skating, dance classes, rock climbing, go-karting, running together, etc.

Final thoughts

A well planned date can do half the work for you, in the same way that a badly planned (e.g. dinner and a movie for a first date) can feel like an awkward, uphill struggle; like trying to light a fire with damp twigs and a wet mop.

A well planned date will help you to have fun and build a relationship easily without having to worry about where to go to next or how you’re going to make your move.

So invest some time into thinking through your date plan, because not only will it make your date better, but you can repeat the same date plan again and again with different women or even the same woman.

By doing this, you’ll become more familiar, comfortable and naturally confident on your dates, which is always an added bonus.