Congratulations, you’re on a first date! Whether it’s a coffee shop, a cozy wine bar, or a delicious ramen spot, one thing is clear: you’re not here to waste time. You’re tired of the first dates that go nowhere; you’re looking for a partner whose values align with yours, someone you can grow with. But how do you figure that out without making this feel like a job interview and sucking out all the fun? Let’s talk through all the ways you can cut through the BS and get to the real stuff without it going (too) awry.
Break the ice without TOO much small talk
You sit down, and understandably, you’re a bit nervous. Your go-to is to ask what they do for work, but you stop yourself. It feels like too basic of an icebreaker, but what should you ask instead? Try something like:
- If you didn’t have money, what would you do every day?
- What’s your dream weekend look like?
- If you could live anywhere for a year, where would it be?
Focusing on questions like this gets your date talking about their passions instead of just reciting their resume. Plus, it gives you a peek into their personality and whether it matches yours. Do they light up when they talk about travel? Do they dream of a quiet life with an army of pets?
Why this matters: You’re not just looking for someone with a paycheck (although financial stability can still be a value); you’re looking for someone whose values, lifestyle, and dreams align with yours.
Lean into vulnerability
The apps (appetizers, that is) have arrived, and the conversation is starting to flow. You share a funny story about getting lost on your last road trip. Your date laughs and shares a similar story. From there, you take the risk and lean into some deeper topics:
- Sounds like getting lost doesn’t phase you, so what does make you scared?
- What’s something you’ve learned about yourself recently?
- What’s a memory that always makes you smile?
- When was the last time you cried?
- What’s the last white lie you told?
This signals to your date that you’re interested in more than just chit-chat and want to start diving deeper. You’ll also get a good read on how open they are to being vulnerable with you and if that feels like a good fit for what you’re looking for. Don’t be afraid to answer the question yourself—you gotta walk the walk!
Why this matters: Vulnerability leads to healthy emotional connection, which is crucial in a relationship. You want to find someone who can lean into the uncomfortability of that with you, someone who is comfortable sharing the real them with you and who wants to learn more about you as well.
Gauge their values (Without sounding like a job interviewer)
The ice has been broken, and you’re both still on the date (no one has had an “emergency” pop up…). You can dig into what matters! You casually ask one or two of these questions:
- What’s something you’re passionate about?
- What’s a cause or issue you find yourself really connecting to?
- Which is more important to you [add two values here]?
- What do you want to accomplish in the next 1/5/10 years of your life?
Listen closely to how they answer. There are no wrong answers; their values are their values. What is important is how authentic their answer is and how their values mesh with yours. Are their values complementary to yours? Does their answer seem more for the show?
Why this matters: Our values strongly impact how we show up in the world, act, respond to events, and plan goals. For a healthy relationship, aligned values (or at least not opposing values) are crucial. Not only that, but the practice of being able to identify and discuss values with each other is a good practice to begin early.
Future lens
As a bonus section, feel free to throw in one of these questions any time during the date if you’re feeling a connection.
- If you could design your ideal life, what would it look like?
- What are you looking for in a partner?
You’re not asking them to sign a commitment contract, but you’re also looking for someone whose future could possibly line up with yours. If they’re looking to have 3 kids in the next 5 years, and you’re dreaming of traveling the world with a partner in that same time period, it is something to consider.
Why this matters: Your goals don’t need to align perfectly, but you should at least be walking in the same general direction. And while all these are open to change, its also important to now assume things will change, for either of you, if you truly hold these goals as aligned with your values.
Measure compatibility through fun topics
It’s dessert time, so let’s end the date on a lighter note (but still get some good information). You use a more playful question like:
- What’s the most wild thing you’ve ever eaten?
- If you could watch one movie for the rest of your life, what would it be?
- Would you rather…
- Best present you’ve ever gotten?
- Go to karaoke song?
These lighthearted questions help end the date on a playful note, leaving you both with a smile on your face. It also gives you a sense of their sense of humor and interests. Do they laugh easily? Are they quirky? Can you imagine having fun with them?
Why this matters: Compatibility isn’t just about values—it’s also about enjoying each other’s company. Being able to be silly with a partner makes life enjoyable.
Don’t push for an answer
As much as you’re vibing, remember this is still a first date. Ask questions, but don’t push for your date to answer. If they don’t feel comfortable or only feel comfortable answering to a certain degree, that is their choice. You can then decide if you want to spend more time building a space they feel more comfortable sharing or if it isn’t the right fit.
Final Thoughts
First dates can be nerve-wracking, but remember, the goal isn’t to impress them with perfection. It’s to determine if you enjoy their company if your values align, and if there’s potential for a deeper connection. So, ask the quirky questions, be vulnerable with each other, and don’t forget to laugh. After all, the right person will appreciate your authenticity—and maybe even end up with you doing your best karaoke rendition of “Don’t Stop Believin’.”
Dr. Vivian Oberling is a licensed clinical psychologist with degrees from UCLA, Harvard, and Stanford. In her private telehealth practice, she works with adults navigating anxiety, identity shifts, and relationship dynamics—whether they’re dating, partnered, or parenting. She also provides executive coaching and behavioral health advisory support to tech startups and legal tools reshaping how we think about love, marriage, and psychological safety. Dr. Oberling combines 10+ years of clinical expertise with modern, real-world insight to help people move through uncertainty with clarity and connection.
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