10 Stylish deep questions to ask a girl

10 Stylish deep questions to ask a girl
10 Stylish deep questions to ask a girl

   10 Stylish deep questions to ask a girl

The question most people will ask is? Why should I leave the fun moments and enter into tough and uncomfortable conversations?

There are so many fun conversations to have. Why divert into personal and boring questions that might ruin the moment.

This is the mentality of a lot of people. I will answer your questions however, I have a question of my own to ask.

Is there a theory which states that all deep conversations must be boring and uncomfortable?

Please if there is a law like this, I will like to know who propounded this theory. This theory needs instant modifications.

Now to answer your questions, Deep conversations do not need to be boring and uncomfortable. However, there are some factors that affect these kinds of conversations hence, making them seem boring.

If you are one of the believers of boring and uncomfortable deep questions. Well, let me introduce you to the antidote. Something absolutely different but with a greater positive result.

Have you ever heard of stylish deep questions? If yes, have you tried it out. Tell me what you think about it and how effective it is.

What are stylish deep questions?

It basically deep questions with a twist. You are aiming for the same answer however, you are using a different approach.

It is the method of asking a deep question in a more fun and approachable way.

Instead of walking up to a person to say, you lost your dad, right?

Say something like it’s good to have you back, I miss the smiles on your face. This can spark a conversation and lead to the subject you really want to discuss. The major purpose of stylish deep questions is to lighten the mood and prevent awkwardness in a conversation.

Let’s look at an example for easy clarification

2 cute-looking teenagers were in the diner on Saturday. They were chatting happily without a care in the world.

I couldn’t help but watch them from a corner in the room. The waitress approach and ask for their orders which they gave their reply.

Barely 30 seconds after the waitress left to get their order, there was a sudden change in their facial expressions.

The table that was bubbling with joy and laughter was suddenly gloomy. There was a sudden covering of a dark cloud of tension, sadness, guilt, and hurt.

I couldn’t understand what was happening. How can an emotion switch happen so quickly?

I know people experience mood swings but at that moment I couldn’t help but believe that there was something more to the sudden mood swing.

I know you are probably calling me a stalker right now. However, at that point, I didn’t think rationally but let’s look at the bigger picture.

My curiosity is actually helpful to this article, I’m sure I never knew it will be useful to me one day.

Back to my story!!

Five minutes later the girl stood up and almost ran to the ladies’ room.

I went after her to find her crying in front of the ladies’ room, she didn’t even make it inside.

Well, I actually stood by her and after letting her cry for a while. Then I tried to offer her comfort and it was effective.

Pay close attention to these points, the most important lessons are here.

This was our conversation

Me: We didn’t even make it inside? Awesome

Cute teen: Chuckles slightly

Me: Want to share? Listening to people is actually my Job. I get paid for it; they call me a professional “I whispered” to her”

Cute teen: chuckles again, then she replied. My friend got me really upset

Me: … (more details please P.s I didn’t say this out loud)

Cute teen: She asked me if I didn’t eat grilled chicken again because it was my brother’s favorite. I lost my brother 6 months ago.

Cute teen: I’m not mad at her, I am just upset at the way she brought it up.

Me: He could have been my grilled chicken buddy; I love it too.

Cute teen: Really? I thought people prefer fried, baked, or roasted.

Me: Not me, I love my chicken grilled, I taste the flavors better. It’s amazing, I think I have a craving right now. I better include it in my order.

Cute teen: You make me want to try it out??

Me: I’m really sorry about your brother, hard to forget family huh!

From today, I eat grilled chicken to remember my buddy…

Cute teen: Diamond

Me: Cool name

Cute teen: From today I eat grilled chicken to remember Diamond sparkling like his name.

The initial sad situation was diffused. It’s obvious that her friend “hit the nail on the head” Did you notice my stylish deep questions in the conversation?

She obviously hasn’t heard of stylish deep questions, instead of asking directly about her brother.

She should have started talking about the different ways to prepare a chicken. Then mention grilled chicken and dwell on it.

This would have triggered a more positive reaction from her bereaved friend.

10 Stylish deep questions to ask a girl
10 Stylish deep questions to ask a girl

Factors that negatively affect deep conversations

  1. Tone

The tone of your voice when having a conversation matters a lot. People read different meanings from the tone you are using to address a particular subject.

What you say might not be bad, but the way you say it just sounds wrong. We should be extra careful when engaging in a deep conversation.

The tone of your voice can spike an unexpected reaction from the person. Don’t sound demeaning, assumptive, sarcastic, or rude.

These tones should be very far away from your discussion.

  1. Insensitivity

Have you ever heard someone complain about an insensitive friend or partner?

If you haven’t? Well, I have!

I was once an insensitive friend; this was not because I was a bad person. Rather it was as a result of my inability to process negative emotions.

I was practicing toxic positivity which is unhealthy both to me and the people around me.

However, I truly working towards acknowledging people’s emotions and reactions.

Most people are just like the old me, they have a hard time processing their negative emotions. Therefore, they do the same thing to other people’s feelings.

They ask certain questions from a place of insensitivity and disregard for people’s reactions.

  1. Approach

Most people approach a situation without care or prior consideration.

What were you talking about before you made a U-turn to ask a very sensitive question?

What was the previous mood, was it tense, sad, or neutral?

Did you add subtlety to the question or was it direct?

Should there be follow-up questions?

Can you estimate how bad, good, or neutral the response will be?

You need to consider a different approach and the person’s potential reaction. This will guide you in choosing the worst or best approach.

  1. Relationship status

How close are you to this person? This is another important factor to consider.

When you ask certain deep questions and you probably are not really close to the person. They might be more forgiving as they believe the individual is oblivious.

However, if you are a really close friend who should know better. Then the chances of hurting your friend are really high.

Also depending on the hurt individual, the chances of forgiveness might be very low.

10 Stylish deep questions to ask a girl
10 Stylish deep questions to ask a girl

Stylish deep questions to ask a girl

  1. Wow, this is new?

Works perfectly if you notice something new that doesn’t really suit the person. Most times it is really hard to tell a girl that her makeup or hairstyle doesn’t suit her.

However, you can adopt this method by asking her what’s new?

This will immediately spike a conversation. That could lead to telling her that she prepared the last style or you think it suits her better.

Most girls are really sensitive to any compliment about their physical outward.

Try to be smart and subtle.

  1. X or y person which are you: This sounds like a fun question. Some girls might not really understand what you mean.

However, the curious ones will really love to decipher the question.

This is your chance to tell them that X or Y is a game you play with your friends.

To determine if a person still loves their ex or has moved on. From here the conversation about the ex can move on.

Without an awkward silence or completely ruining the conversation.

  1. What’s your Sunday like? If you want to know what religion the girl is, you can ask this question.

It is a worldwide knowledge that Christians go to church on Sunday. If her Sundays don’t involve church activities you can talk a little about her religion through this process.

  1. It’s complicated seems like the new trend now? Please tell me you didn’t board that flight too?

If you want to figure out her relationship status but don’t want to ask her directly. You can begin with this question.

It is tricky but direct. It can even end you a laugh from her.

  1. You seem tired

 If she always comes late for your hangout every time. You can use this approach to find out why.

It is subtle and very casual.

  1. The bank or White House which will you like control of for a day?

If you want to know more about her priority this stylish deep question can be a great starter. The bank stands for money and the White House stands for power.

  1. What do you think about this movie?

If you want to know about her stand in the feminist movement. You can bring up a feminist movie you have seen and ask her what she thinks about it.

This is so much better than asking her if she is a feminist directly.

  1. Living your dream, right? I’m quite envious

If you want to talk about future plans and goals, you can try this approach.

Truthfully compliment her present job or career. Act envious like she’s living her dream and you have not attained that yet.

This can lead to a conversation about other things she hopes to achieve. However, if she is already living her dream life. You will be able to tell from the words she says.

  1. Can you lend someone your most precious belonging?

If you want to determine her level of trust you can use this approach. It is not 100% accurate however it can give you an insight.

If she doesn’t trust anybody with her personal belongings how much more her heart?

10.I Love Zac Efron, he has a nice personality, he is …

This isn’t exactly a stylish deep question however with this approach, you can get her to talk about the qualities she likes in a man.


You don’t have to ruin the conversation mood in order to have a deep conversation. Although deep conversation cannot be compared to fun or casual conversation.

It can still be more fun, less boring, and uncomfortable. If you constantly make the mistake of ruining a hangout. Due to the introduction of deep conversation.

Try out our stylish deep questions, tell us all about the results in the comments section.