Photo by Irena Carpaccio

From guy to girl, let’s be honest here…

Dates can be awkward as hell.

A little while ago a guy likely appeared on your radar and you two got to know each other a little.

Which eventually led to agreeing to go on a date…

But now that the date is around the corner and you’re maybe a little doubtful or nervous:

  • What if it’s weird or awkward?
  • What if HE’S weird and awkward?
  • Will I need a blueprint with the emergency exits?
  • Wait. What if HE doesn’t like ME?!”

I’m exaggerating a little here…

But if you can relate to any of the above thoughts, know that it’s perfectly normal to feel skittish.

As a man, let me also reassure you that MEN have these worries AS WELL!

Sure we play all cool and detached, but DON’T BE FOOLED!

It’s just an act.

So now that you’re going on a date, you can warm things up with a little small talk:

How are you?
The weather is so…
“Omg, did you hear what happened…?

You know, the classics, etc..

Then when the moment feels right, you can ask your date some of the following questions to peak his interest in you.

(Women who ask questions and take the lead are INSTANTLY respected more by guys)

The questions also have the added benefit of you gauging his answers and seeing if he’s OF INTEREST TO YOU.

Almost like a job interview, would you employ him? 😉

Let’s find out!

Question #1 | “What Is The Cheesiest Pick Up Line You’ve Heard So Far?”

“Are you from Tennessee?… ‘Cause you’re the only ten I see.

Terrible, I know.

But it can break some awkward walls.

Ask him (if you dare) and find out whether he’s actually used it!

It’ll give you a taste of his flirting skills (or lack thereof).

Question #2 | “Is There a Thing You Would Never Ever Do?”

Bold, cautious or total wimp?

Time to find out!

Question #3 | “What Things Do You Consider Yourself to Be Good At?”

Like most men, I’ll likely always fall for this one.

We’re just so “humble”, that we’ll never pass up on an opportunity to let every woman in the world know how amazing and great we are.

We just can’t help ourselves! It’s hopeless. 😅

But can he keep himself in check at least a little?

Also, if he isn’t totally self-absorbed he will RETURN the question.

Question #4 | “ What’s the Show to Watch on Netflix or Amazon Prime Right Now?”

You can tell a lot about a guy based on his favorite show.

Is he into series about tough but heartless gangsters?


More the smart detective that solves impossible murder cases…

Or the heavens forbid, has he watched all seasons of FRIENDS a dozen times?

Time to find out which characters your date sees himself in!

Question #5 | “What’s the Best Thing That’s Happened to You?”

The lottery? A job opportunity? Finally managing that backward somersault?

Or if he’s really cheeky, “Obviously, this date with you…”

Question #6 | “Do You Have Something That You’re Proud of That You Haven’t Told Anybody Yet?”

Are you into mysterious guys? Some men have secret projects.

They’re often kept secret while they’re in their delicate development stage.

But maybe you’ve swooned him with your charm already and he’ll want to tell you EVERYTHING!

Question #7 | “What’s Something That Bugs You About the World?”

Are there things about the world that frustrate you?

Personally, there aren’t any for me… Except, you know, almost EVERYTHING that could be fixed or improved!

And he surely has his gripes too.

With this question, you’ll be able to see whether you care about and value the same things or live on the opposite ends of the planet.

Question #8 | “Would You Rather Go to a Family Reunion or an Amusement Park?”

Is his family pleasant or would he rather do anything BUT that?

I for one, would rather go for a walk alone in a graveyard as the clock struck midnight than attend my family reunion.

It’s nothing personal really, we all just collectively hate each other.

How about you?

Question #9 | “What Are the Best and Worst Flavours of Ice Cream?”

This can make or break a date.

You can take this one a step further “Ben & Jerry’s or Häagen-Dazs?

Things can get personal and ugly quickly though, careful with this question. 😉

Question #10 | “What’s the Worst Advice Someone’s Given You?”

Have you ever been convinced to do something by a friend who branded it as GREAT advice…?

That then turned out to be THE WORST thing you could have ever possibly done?

Yeah, me neither.

But let’s find out whether he has!


And there we have it.

10 questions that will undoubtedly keep your date on his toes, you in control and the last time you’re likely to see him.

I’m kidding.

But DO BE CAREFUL not to ask ALL of these questions on your first date!

He’ll think you’re nuts and you and I both know you’re a delightful human being, let him see that side of you…

The crazy can come later. 😬

So, pick only a couple of questions that you like and are actually CURIOUS to hear the answer to.

This will create an organic and super interesting atmosphere.

Plus he’ll see you as deep and be curious to learn more about YOU!

Let me know how your date went (I’m totally curious!) and if you have any questions about the questions.

Leave them in the comments section and I’ll get back to you!


Gabriel Brenner