Relationship questions – Delve deeper without them knowing

Relationship Questions – Delving deeper into the mind

A lot can be attributed to language that can scope out the hidden depths of others without them knowing what you’re prying for. My wife taught me this when we first met, and little did I know that she was ploughing me with a ton of relationship questions that seemed really innocent but gave her deeper meaning to me, as a person. I learned all of this myself, in time, but before I had actually been to my first date with Natalie she had basically laid me bare with her questions. It’s also a great way to extinguish any toxic people before you start fostering some kind of bond between the both of you.

Here are a few of my favourite relationship questions:


What’s your enjoyment?

Or do you have any hobbies? I would always start with this one because there are so many great depths to this question you have no idea. Firstly, you’ll get an idea whether your new attraction is only skin deep, and through their life of no activity will be waiting by the phone 24/7 for you to call. That sort of attitude isn’t attractive or healthy. It will also give you an idea whether their week is full of enjoyment doing their own thing, and whilst being with you is great, they have other things to keep them occupied.

It doesn’t stop there though. Getting an idea what their hobbies are, or what activities drive them wild will also secretly tell you whether they are likely to call off a date with you to watch the football at the pub with their mates, or be too busy waxing their motor to call you back. Hobbies are great, but sometimes it’s also a really good tool to recognise hobbies that have crossed the boundaries into obsession. It’s worth it to ask your potential partner the hobbies that drive them. It’s one of those relationship questions that really give a broader meaning of the person you’re interested in.

Have you travelled anywhere significant?

Always mix this with what sort of strange food have you tried? It gives you an idea whether your potential significant other is culturally open. By that I mean, will they be on the picket lines denouncing all immigrants as a scourge on our society? Or will they be out, embracing the world and all the wonders it has to bring us? My Mum thinks she is culturally open, and has always told me to never judge different races, yet when she travels abroad, and she does this a lot, she mixes with British people, eats British foods, and drinks British liquids. In my mind she may as well have thrown a summer party in her back garden and achieved the same result, right?


Being culturally open also gives you the insight as to whether your partner has a thirst for life. These kind of relationship questions are the best and can be the most in depth. There are also people like me, that have dreamed of travelling the world since they were kids. I always wanted to see the world but didn’t have the education, the funds or the understanding how to make it possible. There was always zest for new and exciting things there. Never discount an eager and willing person and mistake them for a disinterested one.

Tell a sad story and watch their reaction

All great relationship questions should be about emotions, but because people are guarded we need to navigate around this. Sounds a bit cruel to do this, but when you get a chance, slip in one of your sad stories to test out the emotional maturity of the person you’re dealing with. People process emotions on various different levels, and the way they handle your story will be a good tell tale sign of what you’ll be in for over the next few months. If it were me I’d be looking for people that were saying something along the lines of,

“Wow, that made me feel really sad”

Or any sort of recognition that they know what they are feeling and know how to handle it. I mean some people just won’t find it sad, and that’s fine, just as long as they are able to audibly justify their feelings to me, that’s a total winner in my books. It doesn’t need to be a dark secret you’ve locked up for years like a skeleton in the closet, it could be just that you’re late because your nans friend died or something similar.

emotional man

Ask them about their friends

Positivity and forward thinking for me is key, I love asking people about their friends, how they met and how well they get on together. I’m HUGE on treating others with respect and paying kind heartedness forward. People generally have good things to say about their friends, because they’re friends after all. If they don’t, then that’s a red flag for me. I start to wonder if they say this to their face? Or is that something they would say behind their backs? Then I start to wonder if that’s how they’ll treat me in future? Not that I’m bothered, but I generally find people that talk about others behind their backs sneaky and underhanded – it’s all cut with the same cloth of deception. Friends is a great topic of relationship questions to ask them, to delve into the deeper psyche of your potential partner.

I’ve also found that people who have nothing good to say about their friends, always placing the blame on them for instances outwith their control that have happened, generally live in a bad place in their mind. I’d like to also add that you’re walking on dangerous ground when talking to someone that doesn’t like to accept responsibility for anything. Usually these people are Narcs and see the world as a big messed up competitive arena. Stay well away unless you want to have your soul sucked out through your nose!

Where do you see yourself in ten years?

A lot of people misread this one. A lot of people have serious ambition and would like to see themselves do well in this world, but most people lack the drive to see it through. If you asked me ten years ago what I wanted to do I’d have said I wanted to be a manager in a fortune 500 company, earning loads of dosh, draving ferraris and holidaying lots. But if you had asked me how I was going to achieve that I wouldn’t have had the first idea how to achieve it. Most people don’t, and have a lazy streak a mile long. People want success but they don’t want the backbreaking work and screaming failure and sacrifice that comes with it. It’s why the ‘make money’ niche is so popular and profitable.

make money

Anyway, with these types of relationship questions it’s a topic you need to dance around without getting into too much depths or judgements. You can generally get an eye for what people are like. If, say, they see themselves in something realistic in ten years and have a step by step plan of how they are going to achieve it, then WIN! I’m such a little psychology burrower. I’ll say,

“So David, where do you see yourself in 10 years? Wow? Really? The Prime Minister? How will you achieve that then?”

Seems innocent enough, right? But it can tell you so much more about that person by following with the ‘how?’ part. I’ve always envisaged something amazing for myself, but ten years ago I had no idea how, and if I was brutally honest with myself I wasn’t interested in having what it took to do that. It’s only something I’ve developed over the last five years. The will to suceed.

Someone who has the oomph to see it through will have a good idea of what they are going to do, and it will also be very realistic!

Be realistic

No-one is perfect, and if you’re both young it takes quite a lot of life experience to develop a better understanding and appreciation for life. There needs to be room for growth. When my wife first met me I’ll admit I was very rough around the edges and couldn’t see the ocean for the sand, but she helped with that. I was willing to grow and expand my mind beyond even my comprehension, it might be worth your while allowing for that. Don’t expect someone perfect to come along a perfect fit for you. Allow yourself and them a period of time to grow into each other, don’t expect peace and harmony straight away.

Relationship questions - delve deeper without them knowing
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Raymond is a Mental Health activist and cryptocurrency enthusiast. He fuels his activism by taking to the web and trying to create core change in the way people interact. As an ex-Community​ Manager, Raymond has a unique approach to communication and relationships and believes the way forward in life is improving the interactions between one another. Raymond started his blogging activities as a way to heal from a chequered past, and through this, his blog has become something far more empowering than he ever imagined. And thus, The Relationship Blogger Magazine was born.


  1. Hey Raymond
    This is a great article. I loved the way you discussed the most important aspects of the relationship in the most simplified manner. This is not just inspiring but everything that you have discussed is easy to implement as well.
    I came across this website,, which has some great survey questions on love and relationship. It would be great if you can check it out and write your next article on relationships based on something like this.
    Thanks in advance!

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