Creating REAL Connections
10 Questions to Ask Your Boyfriend
Behind the initial chemistry and how well you get along with his friends, how real is your emotional intimacy and connection with each other?
Showing your true (crazy) colours and being your complete authentic self takes time in any relationship. In order to fully let the walls down, there needs to be some level of trust established and vulnerability shared from both sides. Even if you’re willing to get deep and talk about some harder topics, he might not reciprocate and that’s scary! However, it is all part of the process of building a solid relationship - it’s the foundation upon which profound connections are built.
So why not turn this process into a fun and engaging game? I’ve curated ten questions in an order that starts light and fun but then deepens as you become more comfortable opening up to each other. Let’s dive in.
1. What does your dream holiday look like?
This is a great departure point for talking about the future. Maybe you can plan a holiday together and work towards a common goal? Plus, traveling really tests the relationship with a couple because you’re practically living together for a period of time and navigating all sorts of challenges.
2. If you could have any Superpower what would it be?
Add a touch of whimsy to your discussions. This will keep it super light and fun building that comfort between the two of you. Activating the creative receptor in your brain also enhances empathy which will come in handy for later topics of conversation.
3. Describe your perfect day from morning to night - No Limits!
Invite your boyfriend to paint a vivid picture of his perfect day without any constraints. This will really show you where his true values lie. Does he start the day with a workout because fitness is important to him or does he go for a swim at the beach because he likes to connect with nature? Hopefully there will be a few activities that cross over between both your dream days to gauge compatibility.
4. What’s your favourite childhood memory?
Memories about our childhood are important because our interpretation of those memories shape who we are as adults. Making sense of our past is not only essential for understanding who we are, but why we have our values and beliefs. Reliving a nice and nostalgic memory could be an insight into your partner's core values and beliefs.
5. What’s your dream date night?
Okay, it’s time to spice up these questions a little bit. At least with this open ended question, there’s the potential to divulge all sorts of information, from their favourite activity, restaurant and potentially what they’d like to do after the date! Keep notes for any special occasion coming up like their birthday.
6. If you could have dinner with anyone dead or alive who would it be?
This is actually a really great question revealing who they might be inspired by or what qualities they admire in people. I was really surprised when my boyfriend answered that he’d like to sit down with his Great Great Grandfather. He really values family and is deeply interested in his heritage which I found very interesting. It inspired me to take more interest in my own ancestry.
7. What’s your biggest fear about the future?
It’s time to dig a little deeper and share something personal with each other. Fears are often personal because they can be coupled up with other hard-hitting emotions like shame or anger. Understanding each other's concerns builds trust. Being able to empathise and sit with each other through shared vulnerability strengthens your connection.
8. What’s your spiciest fantasy?
Although this question sounds fun and saucy, it can be uncomfortable sharing sexual desires openly. However, encouraging this dialogue in the relationship will open the door to more conversations in the bedroom, expressing what you like and dislike so you can have fun, safe and exciting sex.
9. Does everything actually happen for a reason? Why / why not?
This question is directed at their spirituality. Although your beliefs don’t have to align, it’s interesting to see how the other person feels about their place in the universe. You may have some heavy past experiences that may shape the answer to this question. It’s best to stay open and kind when listening to their views.
10. Where do you see yourself in five years?
Conclude your game with a glimpse into the future. Discussing short and long term goals will identify if you’re both on the same page or not. Does your boyfriend want to travel, move overseas, buy a property, study, start a family or start a new life on Mars? (NASA’s actually recruiting for that!). It’s good to know if you’re both headed in a similar direction, so you can pave the way for shared dreams and continued growth.
As you navigate through these questions, embrace the joy of discovering more about yourself and each other. If you’d like to dive deeper, I’ve created a set of Connection Cards with 100 unique questions ranging from easy, medium and hard. Get the free mini deck of Connection Cards from my website now so you can continue the conversations and build a more meaningful connection between the two of you.
These conversation cards are the departure point for cultivating meaningful connections, guiding us on the path to discovering our common humanity.
100 question cards with 3 levels of progression so you can playfully match the questions to the flow of the conversations
Ethically designed and produced in Australia prioritising quality and sustainability
Luxury soft-touch box with gold-foil finish to elevate your gifting experience
Whether for intimate one-on-one conversations or lively group chats, these Connection Cards are the perfect gift to deepen authentic connections.
Bloom as you are, Maddie xx
