Most people think they know someone after a handful of dates: favorite color, middle name, whether they prefer dogs or cats. But real understanding? That takes work. And honestly, small talk about the weather or what you did last weekend won’t cut it.
Getting to know someone on a deeper level means you’ve got to take some risks. You need to ask the weird questions, create situations that reveal who they really are, and pay attention to the moments when their guard drops. So yeah, skip the surface stuff and try these instead.
1. Talk About Where This Whole Thing Is Going
You can dance around it for weeks, but eventually someone’s gotta bring it up. What are we doing here? Where do you see yourself in a year? Do you want kids, marriage, or are you happy keeping things casual? These conversations feel awkward because they are awkward, but they’re necessary.
The beauty (and terror) of this conversation is that you’ll know pretty quickly if you’re on the same page. Maybe they want to travel the world for the next five years while you’re ready to settle down. Or maybe you both want the same timeline but different destinations. Either way, you’ll save yourself months of wondering “what if” by having this talk sooner rather than later. Plus, someone who can handle a real conversation about the future without freaking out? That’s already a good sign.
2. Show Them Things They’ve Never Heard Of
Take them to that Ethiopian restaurant you love, play them that obscure band from the ’70s, or introduce them to your favorite podcast about deep-sea creatures. The point here is to share something you actually care about, not something you think will impress them.
When you show someone a piece of your world, you’re basically saying “this matters to me, and I want to know if it could matter to you too.” Their reaction tells you everything. Do they lean in and ask questions? Do they try even if it’s weird or unfamiliar? Or do they check their phone and wait for it to be over? You’ll learn whether they’re curious about your interests or whether they’ll only engage with what they already know.
3. Swap Stories About the Times You Had It Completely Backwards
Remember when you were so sure you were right about something, and then… you were embarrassingly wrong? Those stories are gold. Maybe you misjudged someone, or you had a terrible first impression that turned out to be completely off base.
Sharing these moments does two things: it shows you’re willing to admit when you mess up (huge), and it gives them permission to be imperfect too. Someone who can laugh at themselves and own their mistakes? That’s the kind of person you can actually grow with. Plus, these stories are way more entertaining than the highlight reel everyone else is showing off.
4. Ask Them How Their Upbringing Was Like
Family dynamics shape everything: how you handle conflict, what you expect from relationships, even how you deal with money. So ask about it. What was dinner like at their house growing up? Were their parents affectionate or distant? Did they have siblings they fought with or confided in?
You’ll start to see patterns. Maybe they learned to avoid confrontation because their parents screamed at each other every night. Or maybe they’re fiercely independent because they had to be. Understanding where someone comes from helps you understand why they do what they do. And if they’re willing to go deep on this topic (instead of giving you the sanitized version), you know they’re ready for a real relationship.
5. Let Your Weirdness Fly a Little and See If They’re Into It
Everyone’s got quirks: weird collections, unusual hobbies, strange fears, whatever. Stop hiding them. Tell them about your obsession with true crime podcasts or your extensive knowledge of Lord of the Rings lore. Show them your terrible drawings or your weirdly specific Spotify playlists.
The right person won’t judge you for being yourself. In fact, they’ll probably think it’s endearing (or at least interesting). And if they react with confusion or mockery? Well, better to find out now than six months in when you’ve already caught feelings. Authenticity is scary, but it’s the only way to find someone who actually gets you.
6. Pick Something That’ll Push You Both (Not One Person)
Go rock climbing, take a cooking class, try an escape room: whatever gets you both out of your comfort zones together. The key word here is “both.” If only one person is struggling while the other breezes through, you’re not learning much.
When you’re both in unfamiliar territory, you get to see how they handle challenges. Do they encourage you when you’re frustrated? Can they laugh when things go wrong? Or do they get competitive and weird? You also get to see if you can work together toward a goal, which (spoiler) is basically what a relationship is. Success or failure doesn’t matter as much as how you handle it together.
7. Watch Their Face When They’re Deep in a Story They Love
Pay attention to what lights them up. When do their eyes get wider? When do they talk faster? What makes them animated and excited? Maybe it’s a story about their nephew, or a trip they took five years ago, or a project they’re working on.
People reveal who they truly are when they talk about what they love. You’ll see their values, their passions, and what they care about most. And honestly, watching someone get genuinely excited about something (even if you don’t totally understand it) is one of the best parts of getting to know them. If they never light up about anything, though? That might be worth noting.
8. Talk About Stuff That Means Something to Both of You
Having shared values are the foundation of any real relationship. You don’t have to agree on everything (boring), but you need to align on the big stuff. Politics, religion, how you view money, whether you believe in therapy, how you treat service workers: these things matter.
The easiest way to figure this out? Bring it up naturally. Talk about current events, discuss something you saw on the news, or ask about their volunteer work. You’ll get a sense of their worldview pretty quickly. And if your core values clash in a major way, at least you’ll know before you’re in too deep. Compatibility’s not about liking the same movies. It’s about respecting how each of you moves through the world.
9. Hang Out Where They Live and See How It Feels
You can learn a lot about someone from their space. Are they organized or chaotic? Do they have plants (alive ones)? What’s on their bookshelf? How do they decorate? All of these details tell a story.
Beyond the physical space, notice how you feel when you’re there. Can you relax, or do you feel like a guest who has to be on their best behavior? Do they make you coffee without asking, or do they treat hosting like a chore? Someone’s home reveals their priorities and their lifestyle. If you can’t picture yourself being comfortable there (or if they never invite you over: red flag), that tells you something important.
10. Ask About Their Favorite Movies or Books
Yeah, yeah, this seems basic. But the way someone talks about their favorite movie or book tells you way more than the title itself. Do they remember specific scenes or quotes? Can they explain why it resonated with them? Or do they shrug and say “it was good”?
Someone who can articulate what moves them emotionally or intellectually is someone who’s done some self-reflection. And when they share their favorites, they’re giving you a window into their inner world. Pay attention to the themes: do they love stories about redemption, adventure, family, revenge? Those themes probably matter to them in real life too.
11. Show Them Something You Made By Yourself
Whether it’s a bookshelf, a playlist, a recipe, a piece of art, or a side project you’ve been working on: show them something you made. It doesn’t have to be perfect (in fact, the imperfections make it better). The point is to share something that required effort and care.
When you create something and share it with someone, you’re being vulnerable. You’re saying “I made this, and I’m proud of it, even if it’s not professional-grade.” Their reaction will tell you if they appreciate effort and creativity, or if they only value polished, Instagram-worthy results. Someone who can celebrate your handmade thing (even if it’s a little wonky) is someone who’ll celebrate you.
12. Watch How They React in Times of Chaos
Plans fall through, restaurants lose reservations, traffic gets bad, phones die: life happens. And when it does, you get to see who someone really is. Do they roll with it, or do they spiral? Do they blame you, blame themselves, or laugh it off?
Stressful moments strip away the polished version people present on dates. You’ll see their coping mechanisms, their patience levels, and their problem-solving skills. Someone who can handle a minor disaster with grace (or at least humor) is someone who’ll be able to handle the bigger challenges life throws at you. And if they melt down over something small? Well… imagine how they’ll handle something major.
13. Plan Something You Both Agree to Doing
Collaboration is underrated. Pick an activity and plan it together: not one person taking charge while the other nods along. Maybe you’re planning a day trip, a dinner party, or even a weekend getaway. The actual event matters less than the process of planning it.
You’ll quickly discover if you can make decisions together. Does one person dominate? Do you both compromise? Can you navigate disagreements without someone shutting down or getting defensive? Planning reveals communication styles, decision-making patterns, and whether you can actually function as a team. If planning a single day trip feels like pulling teeth, imagine planning a life together. (Yeah, exactly.)
14. Find Out What They’re Really Up to When No One’s Around
What do they do on a Tuesday night when they’re alone? Do they read, cook, game, scroll endlessly, work on a hobby, call their mom? Their solo time reveals their true interests: the things they do because they want to, not because anyone’s watching.
Someone who has a rich inner life and knows how to be alone is someone who won’t need you to entertain them 24/7. They’ll bring their whole self to the relationship instead of expecting you to fill all the gaps. Ask them what a perfect solo evening looks like, and really listen. You’ll learn what recharges them, what they value, and whether they’re comfortable in their own company. (If they say “I hate being alone,” proceed with caution.)
15. See How They Handle Money in Real Situations
Forget asking about their savings account or retirement plan (way too formal for early dating). Instead, watch how they actually deal with money when you’re together. Do they stress about splitting the bill down to the penny, or are they relaxed about taking turns? Do they tip well? Do they complain about prices constantly, or do they spend thoughtfully?
Money reveals so much about someone’s values and anxieties. Maybe they’re generous but terrible at budgeting. Or maybe they’re frugal in a way that feels controlling. Neither is necessarily bad, but you need to know if your approaches will clash down the road. Pay attention to whether they talk about money with shame, pride, anxiety, or ease. Those patterns will show up in every financial decision you might make together later.
Ask Me Anything