5 simple questions to help you and your partner have deeper conversations

Every morning after we take turns cuddling our little girl in bed and pushing her on the swing (come rain, hail, or shine), I (Rog) make us breakfast and French press coffee. Kim and I then head to the veranda of our little cottage, where we chat for at least 45 minutes. While our little one enjoys her breakfast, watches cartoons, and plays with her toys (she enjoys her space), we dive right into the deep conversations that keep us connected. Given our busy lives raising a child with additional needs and running our own business, these morning moments are vital to us.

But we get it. Even in strong relationships, finding time to discuss matters that go beyond simple life operational chit-chat can seem almost impossible. With life’s pace continually accelerating, we often find ourselves caught in the day-to-day grind, missing out on genuine, meaningful interactions with our partners. I don’t mean merely discussing routine, how-was-your-day kind of conversations; we’re talking about strategy, dreams, the real-life stuff that often goes unsaid because these discussions are often tricky to have.

But it’s essential to have these conversations – regularly. We’re all evolving, each day bringing subtle changes. If we don’t keep up with these transformations through authentic and pricing discussions, we risk gradually growing apart. After all, understanding each other is not a one-time event. We’re constantly changing, and those cumulative daily changes add up to bigger changes over time. Without frequent, sincere, and probing conversations, we risk losing the intimate knowledge we once gained from those deep and meaningful exchanges we had early in our relationship – when life seemed simple. Plus, these intimate dialogues also aid in understanding ourselves just as much as our partners.

Of course, at times, we might need a bit of assistance, a conversation starter to get the dialogue moving. We’ve learned through experience that tossing out questions like “What are your dreams and aspirations?” can be somewhat intimidating. However, it doesn’t have to be that daunting. Often, the simplest questions can help us peel back the layers and delve deeper. So, to give you a kick start towards those meaningful interactions, here are five simple yet insightful questions designed to break the ice and deep dive in what matters:

1. “Can I do something to support you this week?”

This question goes beyond just showing that you care. It invites your partner to voice their current stressors, opening the door for honest discussions about the challenges you’re both grappling with. It not only expresses genuine empathy but provides an opportunity for you both to work together to tackle these obstacles. This question can lead to a deeper dive into the pressures that each of you is facing.

2. “If we won the lottery tomorrow, what would our life look like in three months?”

This question is more than just a fun hypothetical; it’s an engaging visualization exercise that can offer rich insights into each other’s dreams and values. The answers might surprise you. In our case, Kim and I often find that our ‘dream life’ isn’t significantly different from our

current one. Understanding this can often highlight a path forward and spark ideas for taking tangible steps towards those dreams.

3. “What was the high point and low point of your last month?”

This question was a favourite at my Auntie’s house, where all the family, post a birthday celebration, would share their “peak of the day”. Although initially met with groans, it eventually became a moment of gratitude and a way to share insights on recent life events. Implementing this question in your weekly conversations can offer a window into what brings your partner joy and what currently causes them stress. It also provides insights into recent life events and encourages a practice of gratitude.

4. “If we had more time and money, what’s something you’d like to start or do more of?”

This question can uncover desires that might have been sidelined due to life’s relentless demands. It’s an invitation to discuss how to bring these aspirations to light, so they don’t lay hidden in regret. It offers a glimpse into what might be missing from your partner’s life, what they yearn to pursue, and can lead to thoughtful discussions about how to turn these desires into a reality, potentially even something you can embark upon together.

5. “What did you learn from something you did yesterday?”

This question was a staple back when I worked a 9-5 job and led a team – I asked this every week. It helped my team see their work as more than just operational tasks for “the man” but as daily opportunities for their own personal and professional development. Sharing daily lessons learned with your partner can highlight the value of every day, which is especially crucial when those groundhog day feelings start to creep in. It nudges you both to see each day as an opportunity for growth, not just another tick on the calendar or spin on the hamster wheel.

Remember, these questions are meant to start conversations, not interrogations. They’re intended to provide a simple gateway to explore your partner’s thoughts and feelings. It’s all about growing together. As I often say on our podcast, “if you aren’t growing together, you are likely growing apart.”

And when your partner answers, really listen. Be present in the moment, validate their feelings, and respond with empathy. If it doesn’t work the first time, don’t be discouraged. Dust yourself off and try again, and be prepared to be vulnerable yourself, because once the conversation starts, it can really start to flow.

Head to your fave podcast app and tune into the latest episode of Living the Team Life to hear relationship conversations by real people, for real people.