Best 21 Questions For A New Relationship To Build Connection

Steffo Shambo

Updated on Aug 22, 2022
mature couple in love at night in the city

Entering into a new relationship as a man can be daunting. 

However, with these deep 21 questions for a new relationship, you’ll be sure to decide whether this is the woman for you.

Too many men focus only on impressing the woman early in the relationship. This is the time for you to assess whether this is the partner you need in life.

Know that if you’re looking to reignite passion, intimacy, and trust in an established relationship here are the check in questions you need.

Now though, let’s get back to brand new relationships!

Again, one thing many men struggle with during a date is the false expectation that the ultimate choice is all on her! 

You need to ask questions to see if you are both a match. And also for her to see how approachable and socially adept you are— an alpha male who is confident and has standards for himself and his partner. 

Not every woman is going to become your lifelong partner and connect with you on a soul-deep level.

21 questions for a new relationship to thrive

  1. What are you looking for in a relationship right now?
  2. How do you deal with arguments?
  3. Who, when, and why did you break up with your last partner?
  4. What’s your favorite way to be creative?
  5. Where do you see yourself in five years?
  6. Why should I *not* go out with you?
  7. What’s your guilty pleasure?
  8. Who’s your celebrity crush?
  9. What are your relationship boundaries and non-negotiables?
  10. What are your sexual desires and boundaries?
  11. What are some of your life dreams now?
  12. What’s your job like?
  13. Do you have any passion projects you’re working on?
  14. What’s something you’re proud of?
  15. What’s your ultimate date night?
  16. How do you deal with stress?
  17. What’s your great accomplishment?
  18. Are you a lark or an owl?
  19. What adventures would you like us to go on?
  20. What’s your biggest weakness?
  21. Are you liking how things are going with us?

1. What are you looking for in a relationship right now?

​​Honesty in a romantic relationship is essential

There are so many reasons that people decide to enter into a relationship. They might have recently broken up with a serious partner and are not ready for a committed relationship. 

You both need to be on board with the shape of the relationship, whether a long-term relationship or a fun fling, which has the potential to be a beautiful experience. 

What’s crucial is that you’re both on the same page and there isn’t any deceit or hidden intentions. 

Also, the dating scene is becoming more diverse, so this is a time to see whether she’s seeking an open relationship. 

On the other end, she might be ready to go the long haul with you. Perhaps, she’s looking for depth, true intimacy, and even marriage. 

It’s important to have clear communication and honesty right from the early days.

2. How do you deal with arguments?

In an ideal partner, arguments will arise, but always stay respectful. 

You want a partner who can listen in an argument, hold more than one viewpoint, and take ownership of their mistakes.

Women who become passive-aggressive, shut down, or scream and become violent have inner work to do. 

You deserve a woman that treats you with respect, just as you treat her. Don’t settle for less.

3. Who, when, and why did you break up with your last partner?

Not many men will think to ask these sorts of intimate questions. 

We’re told too often not to bring up exes. However, it’s really one of the most direct ways of learning about any major issues that might arise later on down the line. 

You can also ask questions around:

  • Who instigated the breakup?
  • Why did things end?
  • How long ago was it?

The important thing is you will gain a deeper level of understanding of any relationship shadow patterns. This gives you a chance to evaluate whether you want to continue with the relationship. 

Know that without serious inner work on her end, it’s likely that previous relationship shadows will likely creep into your relationship too.

4. What’s your favorite way to be creative?

shot of young woman painting a large canvas
There’s nothing sexier than a woman with a lust for life. 

Likewise, a woman without hobbies and her own life can spell disaster in a relationship.

You might find that she is constantly waiting for you to meet up as she has little that excites her in her own life.

5. Where do you see yourself in five years?

This can give your new relationship an insight into whether it will last. 

Perhaps her dreams involve moving to a new country.

Are you willing to travel with her? 

Or maintain a long distance relationship? 

It’s great for a new couple to explore these life goals early on.

6. Why should I *not* go out with you?

Everyone loves this fun question. 

Not only because this one is playful but it serves a fundamental purpose. 

As I mentioned at the start of this article, you’re not going to be compatible with every woman on the planet. So this is a time to explore if you are really compatible with your new partner. 

​​Bonus, it’s the qualities that will drive some people away might just be the ones you find hopelessly endearing!

7. What’s your guilty pleasure?

shot of young woman licking an iceream and adjusting shades
Sexy questions such as this show you her sensual side. Is she able to tap into your sexuality?

Notice how you feel here— do you get a rush of excitement at her response? This is a great sign that she can spark your masculine desire with ease. 

You don’t want your woman to feel more like a close friend than an alluring temptress who is able to meet your desires.

8. Who’s your celebrity crush?

This is a good question to suss out her type. 

See the patterns in the men that she describes, and you’ll get a sense of what she values in a man.

9. What are your relationship boundaries and non-negotiables?

shot of successful man in a plush office
Explore through these deep questions whether or not you share similar values. 

This is a great way to prevent you both from wasting time in relationships that simply aren’t built to last. Of course, that’s not the worst thing to happen— it means you can move on and find the real woman of your dreams. 

On the other hand, if you do align with her values, you can invest real trust into the relationship.

Men, trust me, you need this info before going deeper.

10. What are your sexual desires and boundaries?

Find out what she adores during sex. 

What’s her favorite thing to explore? What is she uncomfortable with? How does she like to be touched?

Figure out, through this question, how you would match with her sexually. 

Is she more fiery and passionate?

Or more watery and sensual? 

Or more earthy and steady and slow?

Take this information to decide if her sexual rhythm is compatible with yours.

11. What are some of your life dreams now?

Learning your woman’s desires in life is essential. This personal question reveals her drive. Also, she can see that her man actually cares about her progression and development as a person.

12. What’s your job like?

What people do for a living isn’t half as important as their enthusiasm for the life they live. Work is a large portion of a person’s waking week.

Is she stuck in a rut? 

Has she worked hard to be where she is? 

Is she chasing her dreams? 

A healthy relationship stems from individuals who are fulfilled in their lives. 


Boost your confidence, master your sexuality, and find your purpose.
So you can reignite the passion in your relationship or attract your perfect woman.

13. Do you have any passion projects you’re working on?

An interesting question as it brings up her life outside of work. 

Is she a Netflix and chill type while scrolling through social media? 

Or has she goals and dreams? 

A woman with a passion for life that rivals your own is a must.

14. What’s something you’re proud of?

Creating intimacy and closeness in your new relationship involves rising your partner up.

This can create a volatile response in a woman who is stuck in a shame cycle. Obviously, this is no fault of her own. However, you may be looking for a self-assured woman who knows her value.

15. What’s your ultimate date night?

diary planner with date night reminder
With these romantic questions, you see this person’s standards. Some women will want extravagance. Others couldn’t think of anything better than camping in their favorite place beneath the stars.

Be honest with the type of man you are. 

Does their idea of a good time align with yours?

16. How do you deal with stress?

A person’s ability to self-regulate is extremely important within a relationship. 

Of course, It’s natural for your woman to want a partner she is relaxed around. However, if she is constantly coming to you to relieve her stress, it can make you feel drained. 

So, it’s ideal to have a partner who works on finding balance in their life.

17. What’s your greatest accomplishment?

Here is a time to see how she perceives herself. 

An onslaught of boasting can actually hint toward a deep-rooted lack of confidence.  

A woman connected to her divine feminine energy will simply state it outright with humility. Her confidence in her abilities means she has no desire to show off. 

18. Are you a lark or an owl?

This lighthearted question is surprisingly important. Some people are so highly opposite that it can cause conflict in a relationship. However, it doesn’t mean it can’t work out. 

Just don’t expect a night owl to be dancing in the kitchen with you at 6:30 am. Likewise, a lark hasn’t a chance of staying awake for that movie you throw on at 11 pm.

19. What adventures would you like us to go on?

A man who doesn’t fear commitment is far more attractive in a woman’s eyes. Exploring adventures together in life shows that you are excited for your future together and brings out your playful side.

The biggest lesson to learn here is that dreaming is a powerful part of building a lasting relationship.

20. What’s your biggest weakness?

There is definitely an element of flirting with these kinds of intimate questions. However, this particular one works so well because it’s her choice to read into it!

21. Are you liking how things are going with us?

This is the right question to ask your partner early on. “Are we boyfriend-girlfriend?” can sound childish. And it also gives space to hash out what’s working and what would need improvement going forward. It’s also a good habit to get into checking in to keep the relationship fresh and healthy.

Summary: 21 questions for a new relationship

Do you want to learn how to find and keep the woman of your dreams?

Meaningful conversation and deep relationship questions create connection, but there’s more to building a new relationship.

You need to be the man that inspires and seduces her mind, body, and soul. In the masterclass, I unlock the secrets, as a relationship expert, to maintaining and strengthening an electric connection. 

If you’re ready to receive the knowledge to take control of your power as a man in your relationship— this free masterclass training is for you.

In the masterclass, you will receive practical, refined, and truly life-changing steps to create a relationship with unrivaled levels of passion and intimacy


What are the red flags in a new relationship?

There are many! However, a few include controlling behavior, incessantly talking about a past relationship, not showing listening skills, anger, oversharing mental health struggles, and falling head over heels with their new partner too fast.

How often should you see someone you just started dating?

There is no golden rule. Each person, and relationship for that matter, have their own pace. A word of warning, though: don’t press for something that the other partner isn’t seeking at the time. It’s off-putting and won’t work out in the long term.

What can you do to make your relationship stronger?

A strong couple thrives on communication, trust, and intimacy. If you want to learn to strengthen your relationship with your partner as a man, check out this free masterclass.

What is a good flirty question?

These questions are specifically tailored to make your girlfriend wild for you and create unforgettable intimacy and passion.

Steffo Shambo

Steffo Shambo

Men's Relationship Coach

Steffo is the founder of The Tantric Man Experience, the #1 masculine mentorship program in the world. There he helps men in relationships reignite the passion to restore their marriages from the brink of divorce. And single men attract their dream women naturally with success. He's on a mission to guide men towards an intimate and meaningful relationship, and end the war with their sexuality, so they can finally become integrated men, fathers, brothers, husbands, and leaders in the world.

“It meant a paradigm shift in life.” – Patrik, Sweden
“Life-changing experience.” – Antonio, Italy

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