101 Casual Questions to Know a Man’s Intentions

Reveal His True Objectives in Record Time
white man and white woman in coffee shop asking questions to know the man's intention

In this article, you'll discover...

Table of Contents

The second part of discovering how to attract the right man is knowing the best questions to ask a guy to reveal his intentions, which we’ll cover in this article:

All Readers Welcome

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While this article was written with single women seeking men in mind, as that’s the perspective I can personally speak to, most advice is applicable to all genders and orientations.

So, if you identify outside of a heterosexual female, let me extend a warm personal welcome! 

I’m glad you’re here and hope my content helps you achieve your love/life goals even faster.

- Camille Virginia

How to know a man's true intentions

Whether you’re online dating or offline dating (i.e. dating in real life without apps), when you’re first getting to know a new guy, many dating coaches advise staying on surface-level questions to keep the connection light. 

But I say do the exact opposite: get to a meaningful level with each other as soon as possible so you can see if there’s a real connection and compatibility. 

When you're dating someone, get to a meaningful level with each other as soon as possible so you can see if there's a real connection and compatibility.

black man and black woman sitting against white wall revealing his true intentions
Joanna Nix/Unsplash

Why waste each other’s time talking about topics neither of you really care about (“Did you catch the game last night?”) when you can be getting to know each other on a deeper level and actually enjoy the process?

This is why dating can feel so hard for so many singles – they’re being fed terrible advice, and staying on trivial subjects that reveal nothing about who they truly are or how good of a partner they might make.

The purpose of the dating process is to provide experiences that allow you and the person you’re dating to reveal your true selves, so both of you can see if you’re truly compatible with each other for the long term. 

Aspects like personality quirks, pet peeves, and food preferences simply take time to come out. 

Someone can be on good dating behavior in the short-term but eventually, if they’re not truly embodying the traits they claim to have (e.g. honesty and reliability), the cracks will begin to show.

This is one of the many advantages of offline dating: it’s much easier, and much faster, to determine who a man truly is by spending time with him in person.

To reveal a man’s true intentions, give yourself the time and in-person experiences to truly get to know him. 

To reveal a man's true intentions, give yourself plenty of time
and in-person experiences to truly get to know him.

Investing a few weeks or months to see if a man is right for you is much better than rushing into a huge life decision with him  – whether that’s marriage, having a child together, or even getting a dog together. 

If it turns out a man isn’t exactly who he claimed to be, those situations will be difficult and/or emotional to get out of – and could have been avoided if you’d just given him a little more time to show his true colors.

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Questions to ask a guy to know his intentions

So how do you know if a man has the potential to be the right one for you? 

Instead of sitting around wondering why you don’t have a boyfriend, choose a few questions to ask a guy to know his intentions, which will also make your conversations with each other a lot more fun and interesting.

Even if you feel like you don’t know how to talk to guys, or haven’t yet discovered what triggers emotional attraction in a man, take a look through these questions to reveal a guy’s intentions – organized by category:

Choose a few to bring up in your next conversation with a guy you’re interested in – in person, not online. 

Having a face-to-face conversation gives you the chance to see his facial expressions, body language, tone, and energy behind his answers, as well as encourages a deeper and more powerful connection.

Big thanks to Cool List for inspiring a few of these. 


You can tell a lot about someone and the choices they make based upon where they’ve been and the choices they’ve made in the past. 

white man and white woman chopping vegetables in kitchen asking questions to know intentions
Becca Tapert/Unsplash

Here are 20 questions to ask a man about his past experiences.


Unlike behavior, personality and preferences aren’t typically aspects that people can change about themselves. 

white man in glasses laughing with white woman in yellow jacket revealing his intentions
Jason Goodman/Unsplash

So it’s important to ask about his inherent traits to see if they are ones that you’re willing to accept and welcome into your own life for the long term.

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Even if a man checks a lot of your personality and core values boxes, you need to know if you both share the desire and vision for your life and lifestyle. 

white man and white woman cuddling in truck cab showing her his intentions
Toa Heftiba/Unsplash

Is he a city guy while you’re more of a country gal? 

Does he want vacations to be rugged and adventurous while you’d rather lay by the pool with a dirty martini? 

Ask these questions to find out…

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Just because someone says they want to find a new job, run a half-marathon, or raise $5,000 for the American Cancer Society doesn’t mean they’re taking the action required to achieve those goals.

Ask these questions to discover what he’s prioritizing in his life and if there’s room for you in it right now.


The values of a good man are the most important aspect to look for in a future partner. 

south asian woman holding south asian man smiling
Suzana Sousa/Unsplash

It takes time to see someone’s true values and how they live them in their day-to-day, but you can speed up the process by asking the following questions – then moving on to what to look for in a guy when dating.

Conclusion: Ask key questions to know his intentions

If you want to know when you meet the right man, first you need to get clear on the qualities he possesses. 

After that, choosing a few questions to ask a guy to know his intentions will help reveal if he has the potential to be the right partner for you. 

white woman in dress escorted by white man in woods showing his true intentions
Amber Kipp/Unsplash

But you can’t ask just any questions, they need to be intentional ones that naturally reveal if you and he are on the same page with the big stuff – like having kids, preferred living location, and core values.

The best questions to ask a man you’re dating to reveal his true intentions are divided up into five categories:

After you’ve asked him the questions and received answers that are in line with what you’re looking for, you’ve completed the second of three parts to learning how to attract the right man:

Coming up next...

The next article in our series is Signs of a Good Man: 3 Ways to Reveal If He’s the One – where you’ll discover…

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Picture of Article by Camille Virginia
Article by Camille Virginia

After graduating with a degree in Marketing, I worked in the corporate consulting world for over a decade before starting my business Master Offline Dating to help singles attract love in the real world.

But my true passion (and the secret sauce to my clients' incredible results) is helping people create more meaningful in-person connections in our digitally-disconnected world.

I'm now the #1 Offline Dating Expert, an award-winning writer, and author of two best-selling books. I've also taught over 100 live workshops, reach subscribers across more than 130 countries, and have been featured in major media outlets including the Atlantic, the BBC, and USA Today,

Meet Camille

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