“Can you tell me your life story in 5 minutes?”
This challenge teases out some intimate details. The short time frame puts your S.O. on the spot and invites them to consider the moments that shaped them the most. You’ll learn more about how they see the world and their past, and you’ll get to hear how they repackage their experience into a quick summary. Everyone wants to be seen, heard, and accepted for who they are. Showing genuine interest makes the other person feel like you care about them, and lets them know that you want to get to know them better.
“What’s a memory that always makes you smile?”
Help them relive their favorite highlight. Dip into some nostalgia for a really rewarding way to bond with each other. When your S.O. gets dreamy about the past, you can come along for the ride, too.
“What holds a relationship together?”
Get some insight into what’s actually sustainable for them. Specify that you want to learn what would make a connection last in your partner’s world. All connections are different, so what matters is what the both of you need to feel balanced and happy.
“Are you ready for a serious relationship?”
Invite them to open up about how commitment-minded they are. Maybe they’re excited to settle down or they’d like to keep your dynamic more open-ended. This chat is your perfect chance to see if your visions match up.
“Do you remember anything from our first date?”
Check how sentimental they are and what hooked them. Maybe you remembered how exquisite the food was, while your S.O. can’t forget that mischievous sparkle in your eyes. You’ll both get a refresher on what excites you.
“What first drew you to me?”
Make yourself the topic and learn about your standout traits. When the spotlight’s on you, it’s actually just a fun and sweet moment to romance your partner again. Listen to them gush about your wonderful traits—that way, you can keep playing them up. Feel free to answer this question yourself, too. Move beyond the surface compliments and share why you like them on a deeper level.
“Why’d you end up staying?”
Go beyond the superficial and find out what really matters. After you’ve moved past first impressions, explore what made your partner develop deeper feelings. Then, thank them for being a part of your journey.
“Who are you closest to in your family?”
Learn about the role models or caretakers who shaped your partner. As your S.O. considers your question and reflects on everyone they grew up with, you’ll get a better picture of their circumstances. Ultimately, you’ll also discover who did or did not influence them.
“How can a partner make you a better person?”
This gives you an idea of how you can enhance their life. Listen to what your S.O. expects from a partner and any areas of growth they’ve noticed about themselves. You’ll get a clear answer about how you can balance each other out and lift each other up.
“Can you list at least 10 reasons why you’re grateful?”
See if they look for all the positives or if they can use some help. Maybe your partner naturally counts their blessings or makes a habit of it over time. Even if they don’t, you can give them some extra encouragement and point out what’s worth celebrating.
“What age would you remain for the rest of your life?”
Have them reflect on the version of themselves they love the most. They could’ve taken a while to hit their stride, so they’re happy with who they are now. On the other hand, they might miss who they used to be. Help them keep the magic alive based on who they wish they were.
“What’s your love language?”
Memorize the special way they receive TLC. If they’re familiar with the “five love languages”—praise, favors, gifts, quality time, and touch—ask if they have one they like the most. If they don’t know what those are, just let them express what feels the best for them and treat them to lots of that!
“What’s your favorite difference between us?”
A bit of fun tension can really boost your chemistry. While it’s likely that you share a lot in common, you probably also enjoy each other’s company because you help each other see the world in a whole new light. Look for at least one or two ways you challenge one another and embrace that!
“Do you follow your head or your heart?”
Compare logic to emotions and learn what motivates your lover. They’ll either reflect on this question for a while because they’re not sure, or they’ll be able to answer right away. Talk about why they have mixed feelings or why they’re certain about their choice.
“What’s a serious dealbreaker for you?”
Discuss their boundaries and limits so you can respect them. The best relationships are based on trust and respect. In order for you to navigate your dynamic and show up as a healthy, supportive partner, be clear about what your S.O. won’t accept.
“If you could start a restaurant, what would you serve?”
Ask this to get intel on their favorite type of food and culture. This is a great question to work up their imagination—maybe they’ll think of a dish from back home or their mind will wander to a new place they’ve traveled to. Plus, you can whip up a fave entree they raved about.
“Is it better to change the past or know the future?”
See if they’re more influenced by memories or possibilities. Maybe they wish they could’ve tweaked how their life turned out. On the other hand, maybe they’re interested in what’s in store for them. Either way, you’ll pick up on what matters most to them.
“What does your perfect day look like?”
If they paint a picture of this, you’ll know how to treat them. Maybe they like to start off the day with a strong cup of coffee or some soft piano music. While your lover gets carried away imagining their ideal schedule, you can take notes.
“What would your theme song be?”
Get a feel for how they’d capture their personality. One track can tell you a lot about someone—if it’s upbeat and inspiring, then they might see themselves as super energized. If it’s more moody, they may enjoy being a mystery. Play their choice and listen for some clues.
“What do you think about astrology?”
This gives you some fun insight on how they see the world. Astrology—some live by it while others laugh it off. Wherever either of you stand, you can have a fun discussion about horoscopes, destiny, and the stories you tell about yourselves. You’ll either spark a deep discussion or a playful debate.
“If your house were on fire, what’s the one item you’d save?”
Throw out a wild scenario to see what they cherish. Tell them to make a quick decision based on gut instinct. Once the one possession they can’t go without pops into their head, ask them to explain themselves. You’ll figure out what they’re truly attached to.
“If you were on the cover of a magazine, what would it be?”
You’ll get a taste of their ideal self and their favorite platform. If they can’t imagine even getting that much attention, they’re probably super humble. Still, see if they’ll at least chat about any glossy pages they like the most! If they’re totally fine in the spotlight, you’ll get to learn what they’d like to be famous for.
“Can you describe a dream vacation?”
Dive into the thrill of adventure and daydream together. Make a vision board or just describe the ideal getaway. You can also learn about who’d be the planner and who’d just “wing” everything. By the end of your plans, you’ll see you’re meant to see more of the world.
“Would you rather save your money or enjoy an experience?”
See if they’re very practical or really luxurious. This is a great way to explore your values about money and long-term plans. It’s okay if you both have a different perspective—all that really counts is that you can make a compromise here and there.
“If you had children, what’s one lesson you’d teach them?”
Even if you’re not ready to start a family, you’ll chat about your principles. You can either start off the convo saying it’s just theoretical, or you can admit you’re curious about their parenting style. Then, talk about what wisdom is important and would benefit the next generation.
“Do you respond better to criticism or praise?”
When you learn how they rise to the occasion, you can support them. You’ll also get a “snapshot” of the type of environment they grew up in. Once you’ve chatted about whether they’re more comfortable with constructive or flattering comments, ask what they think is healthiest in the long run.
“When you picture your wedding, is it big or small?”
Chat about an ideal ceremony to hint at getting hitched. This question sounds innocent enough and can even pass as small talk. While your S.O. takes the bait and describes the type of celebration they’d be down for, you can hold onto all that info for the future.
“Where do you see yourself in 5 years?”
Check if you’re a main attraction in that long-term plan. If they bring up a lot of milestones that involve you, you can be sure that you factor into their future. They might just focus on their own personal goals, too—if that’s the case, just be patient and make sure your relationship’s pace works for you.
“Anything you’ve left off your bucket list?”
This is a great opportunity to see how you can pitch in. Either you can help them turn their dream into a reality, or you can offer some fun possibilities if they’re not sure what they should look forward to. They’ll know they can always turn to you for inspiration.
“What’s your ‘happily ever after’?”
Get really sweet and swap fairy tale endings. Let down all your walls and just confess what a perfect love story would look like for the both of you. If you find plenty of common themes, you might just be made for each other.
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