• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

The Modest Man

  • .
  • Topics
    • Fashion
    • Shoes
    • Accessories
    • EDC
    • Hairstyles
    • Cologne
    • See All
  • Reviews
  • Outfit Ideas
  • About The Modest Man
    • Start Here
    • Contact
Home / Blog / Uncategorized
We earn a commission on some purchases you make through our site. Here's how affiliate links work.

18 Questions Couples Should Ask Each Other Every Year

Updated on August 4, 2025 by TMM Staff · Uncategorized

A woman fixing a man’s clothes.
©Getty Images/unsplash.com

Relationships grow, change, and evolve, just like the people in them. What felt right a year ago might feel different today, and that’s perfectly normal. Taking time to pause and ask the right questions can reconnect couples in deep, meaningful ways. These aren’t surface-level chats, they’re designed to open up conversations, spark new understanding, and keep your bond thriving. Once a year, a set of honest questions can do more than routine check-ins ever could.

Table of Contents

Toggle
  • “What made you feel most loved by me this year?”
  • “Is there anything you wish we did more of, just the two of us?”
  • “What’s one thing I did that hurt you, intentionally or not?”
  • “What’s something new you want to try together this year?”
  • “How have you changed in the past year, and what do you need from me now?”
  • “What’s been your biggest stressor, and how can I support you through it?”
  • “Are you happy with how we handle conflict?”
  • “What do you feel most proud of us for accomplishing together?”
  • “Is there anything you’re afraid to bring up with me?”
  • “Do you feel emotionally and physically fulfilled?”
  • “What’s one habit we should drop, and one we should keep?”
  • “Have you felt seen and heard in our relationship?”
  • “Are our goals still aligned, or have they shifted?”
  • “What brings you the most joy in our relationship right now?”
  • “How do you feel about the way we divide responsibilities?”
  • “What’s a boundary you’d like us to better protect, together?”
  • “What’s something you’ve wanted to say, but didn’t know how?”
  • “What do you hope we’re saying about each other this time next year?”
  • Conclusion – Growth Through Curiosity

“What made you feel most loved by me this year?”

A man asking a woman.
©Getty Images/unsplash.com

This question invites reflection and gratitude. It allows your partner to highlight what actions or moments truly stood out and made them feel cherished. It also reinforces those behaviors, encouraging continued emotional investment. It’s a simple way to identify the love languages that mattered most. Sometimes, it’s the smallest gestures that leave the biggest mark.

“Is there anything you wish we did more of, just the two of us?”

A woman asking a man.
©Getty Images/unsplash.com

This taps into the desire for shared time, intimacy, and connection. Whether it’s traveling, date nights, or simply talking without distractions, the answer reveals unmet emotional needs. It can also uncover dreams and interests your partner has been quietly holding onto. Prioritizing togetherness becomes easier when you know what’s missed.

“What’s one thing I did that hurt you, intentionally or not?”

A woman leaning her head to a man.
©Getty Images/unsplash.com

This question takes vulnerability and courage but builds trust when handled with care. Addressing past hurt allows for healing and shows emotional maturity. It doesn’t mean dwelling in the past, it means acknowledging it and choosing growth. Every relationship carries moments of friction; what matters is how those moments are handled.

“What’s something new you want to try together this year?”

A man and woman holding hands.
©Hanna Morris/unsplash.com

Shared experiences strengthen bonds. This question adds a spirit of adventure to the relationship and opens the door to new memories. Whether it’s a cooking class or skydiving, trying something new injects freshness into the routine. It also shows a willingness to grow together, not just side by side.

“How have you changed in the past year, and what do you need from me now?”

A man and woman facing each other.
©Roman Purtov/unsplash.com

People grow in quiet ways over the course of a year. This question acknowledges evolution and invites deeper awareness. It’s about seeing each other as dynamic beings, not static roles. Needs shift as circumstances do, and recognizing those shifts is a sign of active, respectful love.

“What’s been your biggest stressor, and how can I support you through it?”

A man and woman on a couch while having conversation.
©Curated Lifestyle/unsplash.com

Understanding stress from your partner’s perspective fosters empathy. This question opens the floor to emotional burdens that may have gone unnoticed. It also frames the relationship as a team effort, reinforcing partnership over isolation. Support isn’t always about fixing, it’s about standing beside each other through it.

“Are you happy with how we handle conflict?”

A woman looking at the laptop while a man looking at her.
©Curated Lifestyle/unsplash.com

Conflict is inevitable, but how it’s handled defines relationship health. This question helps unpack recurring issues or frustrations in a non-confrontational setting. It invites solutions, not blame. Sometimes, small tweaks in communication styles make a big difference. Transparency about conflict leads to deeper respect.

“What do you feel most proud of us for accomplishing together?”

A woman asking a man that is holding a remote.
©Curated Lifestyle/unsplash.com

Celebrating wins, big or small, creates momentum. It helps couples appreciate their journey and see themselves as a capable unit. Whether it’s surviving a tough year or buying a home, recognizing accomplishments builds confidence in the relationship. Pride can be an anchor during tough times.

“Is there anything you’re afraid to bring up with me?”

A man and woman having a glass of wine.
©Getty Images/unsplash.com

Fear of conflict or misunderstanding can lead to silence. This question creates a safe space to raise unspoken worries or thoughts. It shows emotional maturity and the desire for honest, open communication. Breaking down those walls prevents resentment from taking root. It’s an invitation to deeper trust.

“Do you feel emotionally and physically fulfilled?”

A woman leaning to a man’s chest while at the sofa.
©Toa Heftiba/unsplash.com

Intimacy comes in many forms. This question checks in on both emotional bonding and physical connection. It also clarifies expectations and possible disconnects. Fulfillment looks different over time and through different seasons of life. Asking this directly can prevent assumptions and open the door to renewed intimacy.

“What’s one habit we should drop, and one we should keep?”

A woman wrapping her arms around a man’s neck.
©Getty Images/unsplash.com

Routines shape the emotional tone of a relationship. This question helps couples evaluate patterns that may no longer serve them. Dropping unhealthy habits creates room for growth, while celebrating good ones builds positivity. It’s about evolution through intention, not just repetition.

“Have you felt seen and heard in our relationship?”

A man hugging a woman.
©Getty Images/unsplash.com

Everyone wants to feel understood and validated. This question invites your partner to express where they feel supported, and where they might feel invisible. Being seen and heard fuels emotional safety, which is essential for vulnerability. It can also highlight areas where deeper listening is needed.

“Are our goals still aligned, or have they shifted?”

A man and woman sitting on the floor.
©HiveBoxx/unsplash.com

Life moves fast, and so do dreams and goals. This question realigns priorities and ensures you’re moving in the same direction. It doesn’t mean you have to want all the same things, but understanding each other’s visions helps avoid disconnection. Alignment is about cooperation and shared momentum.

“What brings you the most joy in our relationship right now?”

A man reaching a woman’s hand.
©Toa Heftiba/unsplash.com

Joy is a powerful bonding agent. This question reminds couples of the good that still exists, especially during stressful times. It also emphasizes presence and gratitude. Focusing on what’s going well offers energy for what needs work.

“How do you feel about the way we divide responsibilities?”

A man and woman having a conversation.
©Getty Images/unsplash.com

Partnerships thrive on balance. This question checks whether the household, parenting, or emotional loads feel fairly shared. It helps prevent burnout, resentment, or silent imbalances. Clarity on responsibilities leads to smoother daily life and more respect for each other’s contributions.

“What’s a boundary you’d like us to better protect, together?”

A man and woman at the bed.
©Getty Images/unsplash.com

Boundaries create safety. This question reinforces the idea that protecting mental, emotional, or time boundaries is a shared responsibility. It could be about work-life balance, social obligations, or personal space. Co-defending a boundary creates stronger unity.

“What’s something you’ve wanted to say, but didn’t know how?”

A woman asking a man.
©Curated Lifestyle/unsplash.com

Not every thought or feeling finds the right moment. This question allows space for lingering thoughts, hopes, or concerns to surface. It emphasizes non-judgmental listening. Sometimes, what isn’t said matters just as much as what is. Offering space for the unsaid strengthens trust.

“What do you hope we’re saying about each other this time next year?”

A woman holding the hand of a man.
©Curated Lifestyle/unsplash.com

This future-focused question brings hope into the conversation. It encourages both reflection and aspiration. It’s about shaping the narrative you want to build together, and becoming the kind of partner you’d be proud to talk about. Relationships grow with vision, not just memory.

Conclusion – Growth Through Curiosity

A man and woman drinking coffee.
©Getty Images/unsplash.com

A great relationship isn’t built on mind-reading, it’s built on communication. These annual questions help couples stay connected through honesty, vulnerability, and curiosity. Asking them once a year won’t solve everything, but it opens the door for continuous growth. Love isn’t just about staying, it’s about evolving together, one honest conversation at a time.

Uncategorized Everlane

Related Posts
A woman nagging her man.
18 Things Women Say When They Want You to Take the Lead
A couple refusing to look at each other.
17 Things People Do When They’re Quietly Unhappy in Marriage
A couple at the lawyer’s office.
18 Regrets Divorced Men Admit After Leaving Good Women
A woman confronting her husband she caught cheating.
18 Reasons Men Cheat (And Why There’s No Excuse)
About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

More Articles by This Author

Facebook Twitter Instagram

Join the Club

Never miss a post, plus grab this free guide (instant download). No spam. Ever.

Subscribe Now

Reader Interactions

Ask Me Anything Cancel reply

Got questions? Want to share your opinion? Comment below!

Primary Sidebar

Join the Club

Never miss a post, plus grab this free guide (instant download).

No spam. Ever.

Subscribe Now

Trending Articles
A person's hands typing on a silver laptop displaying the Hulu streaming service interface with various show thumbnails.
12 Series Finales That Sparked Major Fan Backlash
Seiko 5 SNK805
35 Great Watches for Small Wrists
Men over 40 style
“Old Man Style”: Advanced Age Is the New Sartorial Prime
Fashion brands for short men
Stride in Confidence: Where To Buy Clothes For Short Men
Best Business Casual Shoes for Men
Business Casual Shoes for Men: The 8 Best Options to Step Out in Style
Topics
  • Clothing & Style
  • Outfit Ideas
  • Fitness
  • Product Reviews
  • Dating & Confidence
  • Grooming
  • Men of Modest Height
  • Income Reports
Top 10 Brands
  1. Uniqlo
  2. Nordstrom
  3. Warby Parker
  4. J. Crew
  5. J. Crew Factory
  6. Amazon
  7. Thursday Boot Co.
  8. Mr. Porter
  9. Banana Republic

Footer

The Modest Man logo

Home • Blog • Resources • Contact • Advertise

 

Privacy Policy & Affiliate Disclosure • Terms & Conditions • Sitemap

 

As an Amazon Associate I earn from qualifying purchases.

 

Copyright © 2025 The Modest Man (Registered Trademark)