How to Make a Date Special for a “Shy Guy”


How to Be a Memorable First Date

Okay. If there was one question that I can relate to…. this must be that question.

I had great difficulty on many dates as being the guy who is “boring”, “awkward, and “stiff.”

I don’t even want to talk about how afraid I was to even start to become remotely “sexual” with a woman.

That’s right, it took me a couple of years just to figure out how to have that calm, relaxed, and confident vibe I naturally had with my buddies… and be that same guy on dates with women.

For a long time, I believed that it was probably because of my lack of confidence or self-esteem. So I did what other guys did: watched videos on affirmations, read books about “inner game”, and listened to “hypnosis” CD tracks before every date.

None of these things worked.

It wasn’t until I admit to the fact that I really didn’t know how to have a fun, light-hearted, playful “date” conversation that I started to notice significant improvement.

Nobody teaches us this important stuff at the school or college…. so it’s really not our fault.

And do you want to know the worst part? The girl is looking at YOU to take charge. So, you see, if you set a “stiff,” “formal” and “boring” vibe on a date, she is going to follow doing that with you.

This is the reason why it’s extremely crucial for you to learn exactly how to lead the conversation in a fun, playful, and flirtatious manner, right from the beginning, and not later.

Now, in my previous “how to improve your conversation skills” post I went really deep into discussing the mindsets, tactics, and techniques for becoming a “smooth talker.” If you haven’t already, I highly suggest that you go and check out this article. In today post, however, I’m going to discuss mainly on having fun “date” conversations.

The BIGGEST Hurdles You Face on a Date

What underlying issues make “date” conversation more difficult than normal “bar” conversation?

There are basically 3 big hurdles that you face on a date, which you must solve quickly.

  • The loss of rapport.
  • The high-pressure environment
  • The trap of “interview type” conversation

Let me discuss each of these critical issues, one by one.

The first problem you face when you meet a girl for a date is the “loss of rapport.” This usually happens because you two are now in different environments and aren’t familiar with the new dynamics of the interaction.

This is particularly true when you’ve met a girl at a bar or a club.

But it is also true if you’ve met her in the street, online, school, through social circles, or at work.

When you both find yourself in this “private” setting of the date, suddenly it becomes painstakingly apparent how little the two of you actually know each other.

The second biggest hurdle you face on a date is the high-pressure environment.

You and the girl on the date are both so cautious “not messing it up” that neither one of you are willing to take any risks, or say or do anything that might “kill the attraction.”

But strangely… the more “safe” you play it on a date… the more stiff, lifeless and boring the date becomes.

And what often ends up happening as a result of these first two biggest obstacles…. is that you both end up getting stuck into the dreaded “interview mode” conversation and find it almost impossible to get out of it.

In the lack of previous rapport, and in the face of the high-pressure environment, the normal thing for the two of you to do is to start asking each other “boring” questions.

And doing this does nothing but create an endless loop of lack of rapport, high pressure, and boredom.

What should you do to “fix” this?

You must remember that the first hurdle you face on a date is that you both have lost any previous rapport you built with the woman because you both are in a different environment now.

So, in order to counter this hurdle, you must assume rapport with the girl, immediately.

What this basically means is that right from the beginning of the date, you must display the attitude that you are meeting an old lost friend, (which I go in detail in this post here).

You need to ask yourself: how would I initiate a conversation with an old friend?

You would immediately start talking to them, right? You wouldn’t feel any kind of “barrier” that is stopping you from talking to them naturally.

One of the easiest and the fastest ways to do this is to generate superficial rapport talking about “pop culture.”

Many time when we meet our old friend we immediately begin to tell him about a movie we just saw, some sports gossip or celebrity gossip we heard over the radio on the way over, or even ask them some random question like “who sang that song…”

Or we simply mess around with our friends, don’t we?

Now, just imagine how much it would ease the “pressure” of the interaction if you simply “messed around” with her a little bit right from the beginning?

You can easily do this by looking for something to tease her about.

We tease those people we have a connection with.

Beginning an interaction with this “assumed” rapport also ease a lot of tension of the date. Keep that in mind that you both are experiencing pressure… and the faster you can ease that pressure, the easier and quicker it’ll be to create rapport with the girl.

Another best way to ease the high pressure is to show some “vulnerability.” By sharing a slightly shameful story and “disclosing” yourself, you’ll give her permission to do the same with you.

Remember. The less the two of you are trying to “impress” each other… the more fun the both of you are going to have. Establish that “playful, fun, and relaxed” vibe… and she’ll most likely follow along with it.

In fact, your mindset when going out on a date with a girl must be “how much fun can I have with this girl today?”

And, of course, stay away from the dreaded “interview mode” conversation.

The best way to do this is to focus on making statements and telling stories rather than showering her with questions after questions. Recently I wrote an article advising having a “commode story” to tell a woman on a date. What this basically means is that having a two or three interesting anecdotes ready to share. These stories must most preferably show different sides of your personality… and should encourage her to share similar types of stories, too.

Besides telling her stories… focus on making statements that unmask nuggets of your personality and challenge her to uncover sides of her personality too.

A statement like “You totally seem like the type of girl who likes to go the gym and hiking on the weekends… ” is way much better than simply saying “So what do you do for fun?”

Statements are more effective than asking questions because it keeps you in the role of the leader. And it also makes a normal and safe conversation more fun, playful, and engaging because she gets to know how you view her. (and we all are dying to know what the other person thinks about us)

Summing it all together


So before coming on the date, the number one question you must be asking yourself is “how can I have as fun as possible this night?”

And you should completely wipe off any notion of trying to “impress” her.

As soon as you meet for the date… just dive into building rapport. You can easily do this by telling her an engaging story or simply busting her balls just a little bit.

Have a flirtatious “banter” as soon as you can after entering into the conversation. The best way to do this is to use the role of a character. For example, you can try to play the “she is trying to get into your pants” role. In this roleplay, you misconstrue everything she is saying or doing as an attempt to get in your pants. My friend Bobby Rio talks about in detail in this free report, Small Talk Tactics.

Once you’ve “bantered” with her for just a bit… you can then begin having a conversation. Keep in mind to figure out things about her by making statements, prompting stories, and cold reads… and stay away from asking her boring “interview mode” questions like “What do you do for fun?” or “Where did you grow up?” or anything similar to that.

And for goodness sake’s… make sure to start some physical escalation. Even if it as innocent as giving her a high five or touching her on her shoulder when she tells you a funny joke… just make sure to get her used to your touching her. It builds the illusion that you already know her for a very long time.

And for those of you who are struggling with your conversation skills, I highly recommend that you read the conversation skills post now. Bookmark it and read it until it sinks in your head.

Stay chilled,


  1. […] Most guys struggle to start a conversation with women, and then transition to have small talk in a way that sparks attraction. Rather, a lot of guys do the exact opposite. They talk about things that bore women silly and give her no other option than to look for some other guys to talk to. […]


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