How to Be More Interesting on a Date

Dating >First Dates> Be Interesting
by Bobby Rio • Updated: September 08, 2022

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how to be more interesting on a date

Make Women Find You Interesting

I struggled through many dates as the “stiff,” “awkward,” and “boring” guy.

I won’t even get into how scared I was to even begin to get remotely physical with a woman.

Yes, it took me a long time to figure out how to channel that relaxed, confident vibe I had with my friends, and be the same way on dates with women.

For a very long time I thought it was caused by lack of confidence or self esteem.

So I read all the “inner game” books, listened to “self hypnosis” CDs, and said my affirmations before every date.

None of that worked.

It wasn’t until I owned up to the fact that I just didn’t know how to have a fun “date” conversation that I began to see improvement.

Nobody teaches us these things, so it’s really not our fault.

And the worst part is, the girl is looking for YOU to lead her.

So if you set a boring, stiff, and “formal” vibe, she is going to follow right along with you.

This is why it is important for you to know exactly how to lead the conversation in a fun, playful manner, right from the start.

The 3 Biggest Obstacles You Face on a Date

What makes “date conversation” so much tougher than normal “bar conversation?”

There are three big obstacles that you face coming into a date that you need to address immediately.

  1. The loss of (previous) rapport
  2. The high pressure atmosphere
  3. The trap of “interview mode”

Let’s talk about each of these individually.

#1: Losing Previous “Rapport” on a Date

The first thing that you experience when meet a girl for a date is loss of rapport. This happens because you have changed environments and are not adjusted to the new dynamics of the interaction.

This is especially true when you’ve met the girl at a bar.

But it is equally true if you’ve met her online, at work, school, or through friends.

When you’re placed in this “intimate” setting of a date it suddenly becomes painfully aware how little the two of you know each other.

#2: Dealing with the “high pressure” atmosphere

The second obstacle that you face is the high pressure environment.

You and the girl are both so focused on “not screwing up” that neither of you are willing to take any chances or reveal anything that might “ruin it.”

The irony is, the more “safe” you play it on a date, the more boring and lifeless the date will turn out.

#3: Getting Sucked into “Interview Mode”

And what usually happens as a result of the first two obstacles is that you get sucked into “interview mode” and find it nearly impossible to break it.

In the absence of rapport, and in the face of the high pressure, the natural thing for the both of you to do is begin asking each other questions.

And this just creates an endless loop of boredom, high pressure, and lack of rapport.

5 Ways to Spark “the Vibe” on a Date

How to Keep a Date Fun and Interesting

Remember, the first obstacle you face coming into a date is that you have lost any previous rapport you created with the woman because of the change environment.

So, you need to immediately assume rapport.

This means right from the start of the date, you need to present the attitude that you are meeting an old friend.

How would you start an interaction with an “old friend”?

You would just jump right into to talking to them.

You wouldn’t feel any sort of “barrier” preventing you from just talking naturally to them.

Way to Create “Instant Rapport” on a Date

One of the best ways is to create some superficial rapport over pop culture.

A lot of times when we meet a friend we begin by telling them about a movie we just saw, some celebrity or sports gossip we heard on the radio on the way over, or even ask them a question like “who sings that song?”

Or we mess around with our friends.

How much do you think it would ease the “pressure” of the interaction if you just “messed around” with her right from the start?

You can easily accomplish this by finding something to tease her about.

We tease those we have rapport with.

Starting off an interaction with this “assumed” rapport also breaks a lot of the tension of the date.

Remember, you are both experiencing high pressure and the quicker you can diffuse that pressure, the easier it will be to connect with the girl.

Display “Cool Vulnerability” to Diffuse Tension

Another way to diffuse the high pressure is to display some “cool vulnerability.”

This is something else I talk about in several other articles.  By telling a slightly embarrassing story and “unmasking” yourself, you will give her permission to do the same.

The less the two of you are trying to “impress” each other, the more fun the both of you will have.

Set the “playfully relaxed” example, and she will most likely follow.

In fact, your mindset going in should be “how much fun can we have together?”

And avoid “interview mode.”

How to Avoid “Interview Mode” on a Date

The best way to do this is to focus on telling stories and making statements rather than asking questions.

In a recent article I recommended having a “commode story” ready to tell.

This simply means have a couple interesting anecdotes to tell. These stories should preferably display different aspects of your personality, and should encourage her to tell similar types of stories.

In addition to telling stories, make statements that reveal “nuggets” of your personality and challenge her to reveal aspects of her personality.

A statement like “You totally seem like the kind of girl who goes like rock climbing and mountain biking on Sunday afternoons?” is so much better than saying “So what do you do for fun?”

Statements work better than questions because it keeps you in the role of leader.

And it makes the conversation more interesting because she gets to see how you view her. (and we are all obsessed with knowing what other people think of us)

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Putting it All Together on the Date


So going into the date, the main question you should be asking yourself is: “how can I make this night as fun as possible?”

And you should completely drop any notion of trying to impress her.

As soon as you meet her for the date, jump right into rapport.

You can start off by telling her an amusing story or simply busting her balls a bit.

Establish a flirtatious “banter” as early into the conversation as possible.

Using a “Role” to Banter

An easy way to do this is use the role of a character.  You can play the “she is trying to get into my pants guy.”

In this character you misinterpret everything she is doing as an attempt to get in your pants. I go deep into this in the Small Talk Tactics report.

Once you’ve “bantered” for a bit, you can settle into a conversation.

Remember, find out things about her by making statements, cold reads, and prompting stories.

Avoid asking questions like:

  • “Where did you go to college”
  • “What do you do for fun?”
  • “Do you have siblings”

And for god sake’s make sure you initiate some physical touching.

Even if it is as simple as giving her a high five or touching her elbow when she tells a joke,  just get her used to you touching her.

It creates the illusion of rapport.

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