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What to Ask on a Date – 10 Questions to Keep it Interesting

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Date Questions Should Always Remain Simple, Light, and Not Too Serious

To make talking to women easier, stop caring so much about saying the perfect thing and asking the perfect questions. The harder you try, the harder it is to “connect” with her. Don’t worry too much about being unique, interesting, and different. 99% of the time, it has the opposite effect and makes you to seem weird, nervous, and unnatural and leads to a big disconnect.

Everything is easier and works better when you keep it simple. The harder you try when you’re talking to women, asking questions, and getting them to open up, the more likely you are to mess up and seem boring, anxious, or weird.

The Best Date Questions and Conversations Aren’t Perfect

If you were having dinner with your best friend, what would you talk about?

Interactions should be smooth and effortless. You shouldn’t be thinking about what to ask or say next – it should just flow. No agenda. No topic list. Everything should happen naturally. That’s when you have the most memorable and entertaining conversations with women.

Women aren’t being serious, weird, and trying to ask the perfect questions with their best friends – they’re just “whatever” about it.

Think about your closest friend: Do you worry about asking them the “perfect” questions? Do you worry about what to say next so they’ll think you’re cool? Of course not! They’re your best friend. You don’t care about any of that. You’re just having a good time and don’t care what they think. This mindset works with your friends AND it works on dates.

Relax and quit worrying about asking the most “interesting”, “intelligent”, or “never heard” questions. Don’t treat her like a robot who can’t have a normal conversation. She’s a normal person with a normal brain and she thinks a lot of the same things you and your best friend do – you just have to draw it out of her.

When your questions seem rehearsed and unnatural, she has a hard time connecting with you, enjoying herself, and wanting to “progress” the friendship and relationship with you.

Don’t Let It Get Too Serious

An important part of connecting with her is being able to talk about serious stuff but there’s no place for it when you first meet her. The serious stuff later.

Keeping it light works 10 times better. Women are private and they’re not likely to share deep thoughts, emotions, and memories if they don’t know you.

Interview Questions Are Boring

Ask the boring questions later when you’re getting more serious with her.

You have better luck bypassing the “getting to know you” questions and moving straight to the fun stuff. In the big scheme of things, the getting to know you questions don’t matter.

These 10 questions are to draw out her personality and give you an idea of how she thinks, rationalizes, and what she’s like in different situations so you can get a picture of what would be the right thing to ask or say next. You can’t keep the conversation rolling smoothly if you have nothing to feed off of. You have to be able to keep the conversation unrestricted and flowing smoothly from one topic to the next.

Aim For Smooth and Memorable

These questions aren’t meant to be asked one after another. That makes it weird and unnatural. Wait until you see the perfect opportunity to slide one in and it’ll keep the conversation moving along nicely. For example, if you want to know what her favorite food is, wait until she’s talking about food and casually throw it in. It’ll see more natural. Blend questions in with the appropriate topics.

These 10 date questions make the conversation and the interaction memorable – which is what you’re aiming for. When she goes home, she remembers how much she laughed, the fun and crazy topics discussed, and how much fun she had.

So, now that I’ve covered the “theory” of why these 10 date questions work really well, here they are:


1. What Do You Keep Up With / Are You Into?

When she mentions something she did that was “fun” or “interesting”, you can ask this question.

Starting off slow, but you can’t just hit her with crazy questions yet. You have to do some verbal stretches and warm her up.

This date question is to get a basic idea of what she’s about, what she’s into, they type of crowd she follows, etc. A tiny bit boring, yes, but almost necessary. This begins to shine light on what you and her have in common. If you keep up with modern trends, media, music, etc., this will get you moving in the right direction with your follow dialogue and questions.

For the conversation to flow smoothly, you need a decent starting point.

2. What Keeps You From Getting Bored?

If she mentions something being lame or boring, ask this question.

What we do to avoid getting bored says A LOT about us. This question lets you know if she’s proactive, lazy, and if she makes good choices.

There’s so much you can learn without having to ask those questions directly and you can get such a wide array of answers from this question.

3. What’s the Craziest Thing You’ve Done or That’s Happened with You and Your Friends?

If she mentions her best friend or friends, then it’s probably a good time to whip this question out and ask it.

This question gets her opening up, even more, telling you about her best friends, and gives you more of an idea about what kind of person she is.

“Crazy” doesn’t sexual. It means they got in trouble or something funny and exciting happened and it became a great story to talk about.

Women LOVE talking about crazy, fun, exciting, or scary experiences. When she talks about them, her face lights up, her body language opens up, the mood lightens, she’s animated, and you start to see her personality shine through. She relives the moment and feels the positive emotions she felt at that time. It instantly changes her mood, she perks up, becomes happier, and becomes curious of your reaction to her “crazy” story.

This questions works really well, gets good laughs, and gives you a chance to give her a nickname, poke fun at her, and to connect with her on a fun level.

4. If You Had to Run Away and Start Over, Where Would You Go?

If the topic of traveling comes up, pull this question out and lay it on her.

What people do when they’re cornered and where they choose to end up in the world says a lot about them as a person and how they might act in a relationship with you.

What your’e doing is you’re learning the “boring” stuff about her without being boring. You’re not boring questions that cause her to lose interest. You’re disguising what you want to know in the form of interesting and fun questions.

5. If You Had Your Dream Guy But He Was Missing a ______ or Had ______ Wrong With Him, Would You Still Take

A lot women don’t mind crude and weird humor (watch Bill Burr or Louis C. K. for an idea), and it’s fun to create weird, funny, perverted, and twisted situations, sticking women in it, and asking “what would you do?” If she tries avoiding it, communicate high status by saying, “Aww don’t be lame. Just go with it. We’re totally doing this right now and you’re coming with me.” Most women go along without hesitation because you’re being fun and interesting. BUT, the trick to this is YOU HAVE TO MAKE IT FUNNY and unpredictable. The more unpredictable, the funnier and more fun it is.

If she loves Brad Pitt. Ask, “If Brad Pitt was madly in love with you but he was missing every other tooth, would you still take him? What about if his foot was turning a weird color and smelled funny and it was unfixable?” Or “If your perfect dream guy was handsome, rich, amazing, loving, and had everything you wanted but lost his wiener in a freak accident, would you still take him?!”

The reactions and answers are priceless, the conversation can last for hours, and you will, definitely, establish a great connection with her. If she’s cool, she’ll hit you back with her own sick and twisted questions that will have both of you laughing and making weird faces.


6. Pizza Every Other Day For the Rest of Your Life or No Pizza Ever Again?

Again, you’re hitting her with decision questions and seeing what kind of person she is on many levels.

It’s not something you just ask out of the blue but if the subject of pizza comes up, pull this one out and see what she says.

7. Would You Rather Be Stuck With A Guy Who’s Your Perfect Mental and Emotional Match But Super Unattractive or Insanely Attractive but Really Lame, Boring, and Dumb?

This question along with the one about her celebrity crush make it easy to find out how important looks are to her vs. brains and personality. Some women want personality over looks, others prefer looks, and some go both ways depending on the situation.

It’s a tough question, makes her think, makes the conversation fun and interesting, and helps you learn more about her.

8. What’s the Most Embarrassing Thing That’s Ever Happened to You?

We all have embarrassing stories and if it’s funny and entertaining, recounting it can lighten the mood, create good laughs, and create trustworthiness.

If she’s telling you an embarrassing story, she’s beginning to trust you and open up and she’ll trust you even more if you tell her one in return. It makes the conversation pretty fun and memorable and helps you to see that she’s not a robot goddess. She’s human, normal, and there’s no reason you should put her on a pedestal or be intimidated by her.

9. What’s the Dumbest Thing You Ever Bought?

This question just steers clear of all the boring stuff.

We all buy dumb things and it can be funny to remember back and explain what you were thinking when you did it. Besides it being entertaining and providing another reason for you to pick on her, you can learn a lot about her maturity level and her sense of responsibility with this question.

Usually the dumbest purchases are funny conversations when they actually explain what they were thinking and why.

10. What’s the Worst Thing You Did as a Kid that Your Parents Still Don’t Know About?

Women are rarely, if ever, asked this question and their answers make for a good time.

As little girls, a lot of women weren’t little angels like most men believe they were. In fact, they have really interesting stories that will get them talking and talking and talking. Sometimes, they weren’t the one doing the “bad” thing, but they have a great story about their siblings, cousins, or friends and it quickly becomes very interesting and entertaining.

We all enjoy taking a trip down memory lane and while you’re there, there’s plenty of areas the conversation can go. We all get nostalgic talking about the past. Especially women.


When you add up these questions and keep the “fun” momentum going, you and her are in for a fun, interesting, conversation filled night.

Keep the boring stuff out. No one wants to talk about work, family, etc. when they first meet you. It’s too bland and generic.

Get creative with your questions but at the same time keep the questions simple, fun, and interesting. Don’t get too theoretical or abstract but also don’t keep them too plain.

You’re not hiring her for a job – you’re making a new friend who you can laugh with, talk to, share experiences with, and enjoy each other’s company.

It’s that simple but the majority of us are so stuck in our heads that we completely overlook it!

You’re making a new friend, not hiring her for a position. Remember that.

Thanks for reading,

– Marc Summers

For more questions to ask her, check out this article on Amoramargo21 Interesting Questions To Ask A Girl You Like

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I'm Marc Summers

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