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Valentine’s Day in 2026 is less about big gestures and more about meaningful moments. Whether you’re heading out for dinner, planning a cozy night in, or keeping things low-key with takeout and a movie, there are endless ways to celebrate together. (Check out our 55+ Date Night Ideas).
But the heart of Valentine’s Day isn’t really about what you do — it’s about how you connect. Taking time to check in, laugh, and talk honestly can make even the simplest plans feel special. So wherever you end up this year, on the couch, out on a walk, or sharing a meal, use these seven questions to spark thoughtful conversation and bring you closer. You can answer them all in one night or revisit them over time. After all, connection looks different for every couple, and that’s what makes it meaningful.
Scroll for 7 thoughtful questions to ask your partner, according to Kaley Klemp, coauthor of The 80/80 Marriage and TedX speaker.
1. What is really going on with you these days?
This might be our favorite question for shifting the conversation one level deeper. Instead of talking about the social calendar, kids logistics, or home improvements, this question pushes you and your partner to talk about your inner experience of life. It's a chance to share what's really going on, which is the perfect first question for deepening connection and intimacy.
2. What do I do that makes you feel loved?
One of the biggest ideas to come out of the research on marriage over the last several decades is this: each person has a unique way of giving and receiving love. This question invites you and your partner to explore this insight for yourselves. By becoming more aware of the things you do to make your partner feel loved, you can change the game of your relationship because you can now do things they notice more often or with more intention.
3. What can I do more of to make you feel loved?
Here's how you take the previous question one step further. It's about exploring new ways to create love and connection together. One warning here: this question has the potential to trigger drama. So as you express your wish for the things your partner could do to make you feel more loved, be sure to avoid criticism and include appreciation.
4. What is your favorite memory of the two of us together?
There's something about time-traveling back together to those magical early moments of love that fills you with joy and gratitude. Thinking back to these moments offers a powerful reminder of why you and your partner got together in the first place. It can even bring back some of those early sensations of new love.
5. What do you hope our life together will look like in five, ten, or twenty years?
This is your opportunity to dream big and imagine your future together. It's also a way to begin thinking about your shared vision together, which not only gives you a goal to work toward in the future but also a set of priorities to better organize your current life.
6. When do you find me the most beautiful/handsome/attractive?
Now that you've connected more deeply, it's time to balance vulnerability and chemistry. Knowing that attraction is often about how you feel, letting your partner shower you with appreciation and acknowledgement for the moments that you radiate, sets you up to feel your best for the rest of the night.
7. Imagine you could create the most amazing, mind-blowing, night of sex. Tell me what it looks like?
Here's the ultimate erotic question. It's a question that gives the two of you an opportunity to talk through what the most amazing night together might look like. It's a question that also helps you understand each other's unique sexual desires. Just asking and answering this question can also trigger a flood of sexual energy, which just might set up the ultimate Valentine's Day celebration at the end of the night.
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Kaley Klemp is coauthor of The 80/80 Marriage. She is also one of the nation's leading experts on small-group dynamics and leadership development, a TEDx speaker, and the author of three other books, including the Amazon Bestseller The 15 Commitments of Conscious Leadership, The Drama-Free Office, and 13 Guidelines for Effective Teams. A favorite with Young Presidents Organization (YPO) forums and chapters, Kaley has facilitated retreats for more than 400 member and spouse forums throughout the world. Kaley is a graduate of Stanford University, where she earned a B.A. in International Relations and an M.A. in Sociology, with a focus on Organizational Behavior.
