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6 Insightful Dating Questions To Ask A New Partner

couple sitting on sofa speaking about dating questions to ask

If you’ve been dating someone for a little while, you might be wondering what the best dating questions are to ask a new partner. You’re ready to build on your initial spark, and deepen the connection you have. And there’s no better way to do this than by being vulnerable with each other.

That means being willing to actively listen to each other, open up, and receive. This builds empathy and trust between people and brings you closer together. On top of this, it’s a great way to find out more about your partner and see if you’re compatible for a long term relationship.

Asking open-ended questions like these can take the conversation down many unexpected paths, and also help your partner find out a lot more about you. 

6 Insightful Dating Questions to Ask a New Partner

1. What are you too hard on yourself for?

This question will help you figure out more about your partner than you might expect.

Firstly, you’ll get an insight into the inner workings of their mind. This will help you soothe and reassure them when they find themselves in a self-critical funk, and allow you to show them a kinder and more compassionate approach for the future.

Secondly, it will give you a clue into the expectations they have for other people, i.e. partners, friends and family. When someone is hard on themselves, it’s likely they’ll be hard on others for similar reasons.  

2. If money was no object, where would you live and what would you do?

This feels like a fun and light-hearted question at the outset, but it will also help you understand your partner on many levels.

If money was no object, do you both dream of living in similar places, and leading similar lives? 

Do they want to live in a big city, but you prefer the countryside? 

Do they dream of running their own business and working from the beach, but you’re tied to your current job and don’t want to move around?

Would they stop work immediately and treat the rest of their life as a vacation, or would they keep their life exactly the way it is now?

If your answers are similar, then that’s a good sign you’re headed in similar directions. But if you’re on completely different pages, you may need to re-think this. 

3. When do you feel most vulnerable?

There’s no better question to ask to encourage your partner to be vulnerable than by literally asking what makes them feel vulnerable!

Men, in particular, have learned vulnerability is a sign of weakness, and that they must appear strong at all costs. So if your partner struggles to share this with you, give them some time to open up and feel comfortable. Don’t pressure them. 

If they are able to share something real with you, it’s a great sign. It means they feel comfortable with you and trust you enough to open up. It also means they’re not afraid of being vulnerable, even though it’s always a scary thing to do, which is a beautiful thing.  

4. What is the biggest lesson you’ve learned from previous relationships?

Almost everyone has an ex, so don’t let yourself get jealous here. Plus, there’s so much to learn from why our previous relationships didn’t work out. And when we learn the lessons, we grow.

The answer to this question will show you if your partner is mature enough not to blame everything on someone else, reflect on his mistakes, and move forward without holding a grudge. It will also give you a clue on what your partner is likely to expect from your current relationship.  

5. Do you want to get married and do you want kids someday?

Before you ask these questions, it’s important to be clear on your own answers.

Is marriage a must for you, or are you not that bothered about it? Is being a mum something you’ve always dreamed of, or are you adamant you don’t want kids? Once you’re clear on what you want, ask your partner what they want. 

If your ideas are starkly different, then that’s something you’ll have to talk about more and see if there’s any future together. Usually, when two people are on different pages with these big questions, it’s not salvageable, because these are massive life values that nobody wants to compromise on (and shouldn’t have to). 

6. What are the five things that you are most thankful for right now?

When we think about what we’re grateful for, it puts us in a state of abundance, and that feels really good. Is your partner a grateful person, or are they more focused on what they don’t have?

You’ll be able to tell pretty quickly if they struggle with giving thanks, or if it’s a breeze. 

This shows you how your partner generally thinks and views life. Someone who is very grateful is more of an optimist, whereas someone who is stuck in lack is likely to generally be more of a pessimist.

And pay close attention to the people and/or things they’re grateful for. Are they simple, humble things, similar to your own gratitude list? Are they more extravagant, material-based things or a mix of both? 

These are some of the best dating questions to ask a new partner to get to know them on a deeper level. Having real and open conversations from the outset can help build a healthy relationship and make sure you’re both headed in the same direction. 

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