Questions That Create Space for Real Connection…

If you’re looking for questions to ask your partner that improve communication, spark meaningful conversations, and build a stronger connection… you need more than the usual “bucket list” or “perfect date” questions you’ve seen everywhere.

These 25 therapist-curated questions are different.

I’ve hand-picked them from 20+ years as a couples therapist, based on what I’ve seen create real breakthroughs in understanding. They’re a mix of fun, thought-provoking, and deeply meaningful prompts… designed to help couples communicate more openly, feel truly seen, and grow closer.

Whether you’re on a romantic date night, curled up on the couch, or sipping coffee together before the day starts, these questions can bring fresh insight, share laughter, and open the door to deeper understanding.

Deep Conversations Keep You Close.

You used to stay up late, talking for hours… effortlessly curious.

Your unique perspectives were cute at first.

You admired each other’s quirks.

Now, it can feel like you’re living in two different realities.

You just can’t see eye to eye anymore.

Couples often struggle to communicate because they see the world so differently.

Why These Questions Work…

Many lists of questions to ask your partner are light and fun (which is fine), but they don’t always help you reach a deeper level of connection. Over time, healthy relationships need more than casual chats… they need intentional communication that builds trust and emotional intimacy.

These questions are a mix of playful and profound, carefully chosen to:

• Encourage active listening and compassionate communication
• Help you see your partner’s perspective and feel validated
• Improve healthy communication habits
• Support a stronger connection and better relationship satisfaction

25 Relationship Questions to Ask Your Partner:

Get to know your partner even better with these meaningful questions. Reach a deeper level of understanding by skipping the small talk and diving into some deep conversations. Here are some interesting questions to ask your partner.

• What’s one characteristic that you admire about your partner?
• Would you rather live in a treehouse for a year or sail the world on a boat?
• Which shared activities help you feel closer to each other?
• If you could master one skill instantly, what would it be?
• Would you rather hear the good news OR the bad news first?
• What’s one of your favorite memory of us, and why is it special?
• Would you rather be fully accepted or completely understood?
• What’s one way your relationship has gotten better over time?
• Would you rather have a long, deep conversation OR short check-ins throughout the day?
• What could other couples learn from us?
• What helps you stay open during tough conversations?
• Would you rather get comfort OR solutions when you’re upset?
• Which shared activities help you feel closer?
• What advice would you give a younger couple about conflict resolution?
• Would you rather revisit a favorite memory OR fast-forward to your dream future?
• If you could be any animal for a day, what would you be?
• What is something you are working to improve in yourself?
• Would you rather express feelings with words OR through actions?
• What is one of the best gifts that you ever received?
• What’s one difference between us that you love?
• What do you wish we did more of?
• Would you rather have a pet dragon or a robot best friend?
• What are 3 things you’ve learned from our relationship?
• What is one of your favorite photos together?
• What most excites you about your future together?

How to Use These Questions…

You don’t have to ask all 25 questions at once. Here are some ways to make them a natural part of your relationship:

• Pick one a night and talk openly before bed or over coffee

• Make it playful… write the questions on slips of paper and choose at random

• Take a walk while asking them to make the conversation feel lighter

• Practice active listening… summarize their answer, reflect their feelings, and empathize

📸 Pro Tip: Snap a picture of this list so you can pull it out on your next date night or quiet evening in.

Get Back On The Same Page with Understanding.

When my husband and I first reconnected at a friend’s wedding ten years after high school, we could talk for hours and hours. We understood each other better than anyone. For us, deep conversations have always been one of the ways we understand and appreciate each other most.

But when life gets busy, and little resentments pile up, it’s easy to drift into surface-level exchanges. When we make time to slow down, ask thoughtful questions like these, share vulnerable ideas, and really listen with curiosity… everything feels lighter and more connected.

Learning something NEW about each other brings back the spark and reminds us why we fell in love.

Summarize & Empathize To Help Each Other Feel Heard.

Practice the habit of one person being the Speaker/Sender (answer the question), while the other person is the Listener/Receiver (summarizes and empathizes with what they hear).

Take turns being in each role.

Ask follow up questions to explore the deeper meaning.

Remember that summarizing first helps put your brain in neutral so you can really hear your partner, and empathy is a shortcut to connection.

Growing closer takes effort to rewire new patterns.

keep connecting,
Debbie Cherry, LMFT

PARTNER PLAYBOOK: Would you like more fun couples activities? Grab the Partner Playbook here.