First Date Advice

Every guy out there struggles with something different. Maybe it’s communication; maybe it’s inner game, maybe it’s best places to meet women.

Whatever it is, there’s going to be a guru who totally gets it, because he went through the same struggle. YOUR job is to find your stumbling block and absorb every ounce of knowledge you can to overcome it.

That’s why I like to share some of the letters I get from readers. I prefer to protect their anonymity, but if they are experiencing an issue that I think others can really learn from, I’m all for sharing my advice in the hope that it will help others in a similar predicament.

The more different stuff you read, the more likely you are to come across that nugget of advice that totally resonates with you and your experience.



I’ve got a heavy date organized with this CUTE undergrad that I’ve been checking out for the last couple weeks. She sits near me in Philosophy class at college, and we’ve been flirting on and off since about a month ago.

I’m taking her out sometime next week. How can I figure out where’ll be a good place for her to go? I really want to be original, but I don’t want to come on too strong or too cheesy. I know you always say that the ‘dinner by candle-light’ date is way too intense and weird, and I agree with you on that one, but I’m not too keen on just taking her out for coffee either. It’s so bland.

How do you organize a date that’s fun, cool, and interesting, but isn’t gonna make me feel like I’m laying all my cards on the table by being too obvious about how I feel – oh yeah, and that’s do-able on a student’s budget?

-Phil, Colorado

>>>>> MY RESPONSE >>>>>

Congrats on the cute undergrad date. Sounds like it should be a blast.

Aside from ‘kudos to you, my man’, I have just 3 things to say to you, Phil.

First of all: yes, it’s great that you’ve got a date. It’s even better that you’ve got a date with a cute undergrad. Big ups to you.

However, your attitude is of SERIOUS CONCERN to me.

Allow me to be more specific: in your own words, this is a ‘heavy date.’


Call me on this if I’m wrong (which I’m not) … but in the past, whenever somebody I know says they’ve got a ‘heavy date’ or a ‘hot date’ … or any of a hundred similar expressions … it means just one thing: that they’ve LOST THE BUYER’S MENTALITY.

They’ve invested TOO MUCH emotionally and psychologically into the date, and have lost sight of the fact that a first date (and even a 2nd and a 3rd date) are times for YOU to be EVALUATING HER.

It is NOT a time for you to indulge your Inner Pantywaist and start getting all moony about how great she is, how hot she is, and how you really hope that she’s going to like you.

Using phrases like ‘heavy date’ gives me a valuable insight into your perspective on this woman …

… And I can see that you’re carrying your preconceptions of what kind of a person/girlfriend she’s likely to be (preconceptions which, in this case, are probably based on the fact that she is both young and cute) TOO FAR.

In other words, you’re in the process of giving up any power that you’ve got … TO HER.

By going into a date with the mindset of, “Gee, she’s so young and cute. I really want to impress her. I sure hope she likes me, because boy oh boy do I like her”, you are ACTIVELY DESTROYING your chances of creating and sustaining ANY kind of serious attraction with this woman.

That’s not to say that there’s anything wrong with impressing a woman. Of course there’s not. It’s gratifying, a boost to the ego, and it comes with all sorts of juicy rewards.

BUT it should NOT be the be-all-and-end-all focus of your date.

Let me break it down for you: the mindset that you need to have when approaching a date with a woman – no matter HOW young and cute she is – is THE BUYER’S MENTALITY.

Think of her like a car. If you were going to buy a car, would you be thinking, “Wow, this car’s going to be so great. I sure hope this car wants me to buy it. I hope it likes me as much as I like

(I shouldn’t even need to answer this for you, but in case you’re more of a lunatic than your letter indicated, the answer is NO. Big, fat NO.)

You need to be asking yourself: “Is this woman cool enough for me? Is she pretty enough? Is she smart enough? Does she interest me enough for her to be worth my while?”


You have NOT already made up your mind that you like her – THAT’S WHAT THE DATE IS FOR.

The date is a job interview. You are the interviewer, she is the interviewee.

You are interviewing her for the position of your future girlfriend.

(And in case you’re worrying about whether doing this is ‘ethical’ or ‘nice’, don’t worry. If she’s as hot as you say she is, she’ll have enough experience dating to be doing the EXACT same thing with you.)

To cut this short, you’re clearly placing too much expectation on the date. You’re acting as though you have ALREADY approved her for the ‘position,’ when in fact you don’t really know what she’s like AT ALL, and have NO BUSINESS ‘pre-approving’ her for ANYTHING.

Be cool. Be detached. EVALUATE her.

If she passes your criteria and proves herself worthy of you, then – and ONLY then – do I give you permission to get excited.

By the way … this ‘pre-approval’ thing is something that a lot of men do out of sheer lack of confidence with women. They’re not used to being picky (it’s hard to be picky when the pickings are so slim) and years of failure with women has given them an, “I’ll take whatever I can get” mentality.

This mindset will only ensure MORE FAILURE.

Fortunately, it’s not difficult to cure – the whole problem is rooted in a lack of self-confidence, which is something that I’ve taught hundreds of men (including myself) how to overcome.

(Incidentally, that’s how I know these techniques work – because they worked FOR ME FIRST. So I know they’re good.)

If you want to overcome your own issues with confidence and anxiety, then check this out:

Secondly: what is with the “I’m taking her out” line??

DUDE! Don’t you know that the WORST THING YOU CAN DO is to “take her out”??

You are missing my entire POINT here if this isn’t already clear to you!

Look, you’re on the right track with the ‘not wanting to take her out for a candle-lit dinner’ thing. I’ll give you a few points for that.

But again, you have no business ‘taking her out’ for ANYTHING just yet. What has she done to earn the privilege of having you purchase food, drink, or ANYTHING for her at this point? (Being young and cute are NOT qualifiers for this.)

I’ve already said this a million times, but clearly you weren’t paying attention, so I’ll say it one more time: It is NOT YOUR ROLE to be the ‘provider’ here.

This is for your own self-respect – but it’s for HER good, too.

Look, this woman WANTS to like you. She WANTS to be attracted to you. If you go ‘pre-approving her’ on your first date by giving her signals that she’s ‘got the job’, she’s going to LOSE HER ATTRACTION to you.


Because smart, independent, cute, young undergrads are usually pretty onto-it daters …

… and they’ve usually had enough of weak needy men who are desperate for the affections of JUST SUCH a young cute undergrad, and who are perfectly OK flinging cash and gifts at her in the hopes that she will exchange her affections for what he’s offering.

Do the right thing by her! Allow her to feel attraction for you, and don’t screw it all up by making the HORRIBLE mistake of ‘being the provider’ too early!

You will get her affections by being COOL, INTERESTING, PASSIONATE, and ROMANTIC.

NOT by buying her stuff or ‘providing’ for her.

Now ideally, you wouldn’t have mentioned the idea of ‘taking her out’ AT ALL to her at this stage … but it sounds as though you already have, which means you’re forced into damage-limitation mode.

In this case, my recommendation is to make no more mention WHATSOEVER of money to her, or of anything that even IMPLIES money (no more comments about “I’ll take you out” or anything like that.)

When the time comes to pony up, just look at her artlessly, and say something ingenuous-sounding like, “We’re going Dutch on this, right?”

This is like the ELECTRIC KOOL-AID ACID TEST as far as she’s concerned. If she doesn’t acquiesce gracefully, and agree – GRACEFULLY – to pay her own way, then she’s either a gold-digger, or is too hopelessly mired in useless ‘traditional’ ideas of dating to ever be much fun. Either way she’s a game-player, and you should get rid of her.

(By the way, ANY KIND of pouting, sighing, or eyebrow lifting here is grounds for disqualification from the ‘interview’ process. Subtle bitching IS STILL BITCHING, and should be interpreted as the behavior of a ‘ditch me now’ girl.)

So that’s your attitude sorted. Now let’s talk about item number 3: the date itself.

I totally get your ‘I’m a student’ buzz, and can TOTALLY get behind your desire to not spend too much money on a first date (which is something that I encourage no matter HOW much money you earn.)

Throwing money at a date isn’t going to make it a success, and is likely to leave you feeling more like a desperate loser than a world-class stud, which is why I suggest that you create a self-imposed first-date budget and STICK TO IT.

To give you an idea, my personal limit for first dates is $40. That’s quite a lot, considering that my date will be paying her own fair share. You can have a lot of fun for $80 (which is $40 x 2 people, by the way – you did mention that you’re a Philosophy student, not math, so I figured I’d do the sums for you.)

Your own budget is a highly personal and subjective thing, of course, and anything that you’re comfortable with is fine – with one caveat: you should never, NEVER spend more than $100 on a first date, EVER. (Frankly, even $100 is pushing it.)

Spending more than a hundred bucks on a first date, even if she’s paying her own way, is just going to add too much intensity and pressure, and will weird her out. So keep it under the golden hundred.

The good news is that cheapness and originality are not mutually exclusive things. You can have an awesome date for absolutely nothing – and, very often, the cheap dates are actually the super-cool ones anyway.

Basically, you just have to remember what your goal is here, which is to see if she is the kind of chick that you actually want to continue spending time with.

Another goal (if you’ve got any pride at all) will probably be to show her that you’re an interesting, original sort of dude who’s NOT like all the other guys who have ‘taken her out’.

So those are your 2 goals. Keep them in mind.

To fulfill the first, you need to be able to hang out with her in a place where you can talk easily and audibly to one another, and in a place that you can FOCUS on one another. You can’t evaluate her if you can’t talk to her.

Keeping this in mind, you’ll want to head somewhere that’s reasonably quiet and not too distracting – no loud music, crowds of drunk people, etc.

Might I suggest at this point, Phil, that you put your unreasonable prejudice against coffee shops to one side. The coffee-shop is the IDEAL first date, provided you take her somewhere with a little character (this means no Starbucks, for all you franchise-airheads out there.)

It’s perfect for conversation, it’s public (she won’t freak out if safety is a priority for her, as it is for most women), and you get to eat muffins and drink delicious coffee. What’s the problem?

If you DO continue to be biased against coffee-shops, there are lots of other places you can go which are just as good – AND which will help you to prove to her that you’re smart and original and ‘not like the rest’, too.

Museums, for example, are cheap and interesting, you learn cool stuff, and the displays provide you both with heaps of natural conversation starters.

Art galleries are a pretty sweet deal too – cheap too (in fact, usually free), lots of women really dig art, and ESPECIALLY they dig the GUYS who are ‘into’ art. You’ll seem like an intellectual man with a life of the mind, which is pretty hot as far as women are concerned.

Lots of women also like ‘nature’, so if there are any parks nearby or lakes or rivers or something, those are always a good bet. You can ‘go for a stroll’ and just talk and look at the pretty trees/water/whatever. Again, the more public the better, since uneasiness and a consciousness of the Rape Alert in her handbag are hardly conducive to first-date romance …

Another option: a friend of mine has had a lot of success taking women to the pound to look at the puppies and dogs there.

He doesn’t want a dog (and you should definitely NOT consider ‘just getting one’ unless you’re totally serious about it – the time and effort involved in keeping a dog will KILL you if you’re not ready) …

… but he’s a smart guy, and he knows that women will have a great time looking at puppies and cooing over how adorable they are. They can play with the puppies and just hang out – and most
people are pretty un-self-conscious when they’re playing with cute baby animals, which provides a good atmosphere.

His ‘cover story’ for such a great (and cheap) first date is that his niece wants a puppy, and he’s scoping out the options for her – would his date like to come along and help him see whether there’s anything out there that’s cute enough for his super-cute niece?

He’s a smart man, my friend. By the way, that last line there, about the super-cute niece? It’s a jewel. If you’ve been using the rest of my suggestions about demonstrating higher value, etc, and you let that line slip out, you’ll seem like a really cool guy who is ALSO very sweet and good with kids. Don’t forget to use that one.

I’ll talk to you again soon.

2 Comments on "First Date Advice"

  1. Micah Smith | Reply

    Very cool stuff, Thanks!!!

  2. Katrina | Reply

    @ Joanna I think everyone has to just do what is right for themselves according to their beliefs and values. It would be much simpler if everyone just paid for themselves on the first date (however differently they may choose to do it once they get to know each other better) but obviously that doesn’t suit everyone. It seems it’s a bit of a conflict: some men will never see a woman again unless she pays for herself, and some women (unfortunately, I think) will never see a man again if he lets her pay for herself, even if she has offered to do so! I’d advise men to be prepared to pay in the initial dating period, especially the first date (if he has been the one to ask her out) so as not to severely limit their choice of potential partners….. but that’s why I think a coffee is a good idea, so that he’s not having to supposedly show his worth by spending a lot on her! Something some people also suggest is that if a guy prefers a meal to a coffee (assuming that he genuinely likes dining out for its own sake, rather than wanting to impress a date and show his generosity) he can tell her that he’ll be dining at his favorite restaurant on xx night and that she is welcome to join him (and then it’s fine to pay for her, without it looking as if he’s trying to “buy” her approval)!

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