Have you ever wondered why some people are great conversationalists while others struggle with it? Do you notice that those gifted with this particular skill tend to have an easier time making friends and growing closer to other people?
Well, contrary to what most people might believe, being good at conversations doesn’t actually have much to do with extraversion or confidence, says clinical psychologist Dr. Steven Melendy. Because just like every other kind of social skill, it’s one that can be learned and perfected with practice. And if you’ve seen the viral “36 Questions to Fall in Love” psychology experiment on YouTube, then you’d know it works to deepen just about any kind of relationship, too – even with complete strangers!
With that said, if you’ve been wanting to impress a special someone with your great conversation skills but don’t quite know how to go about it, look no further. Here are some topics to spark great conversations with your crush, according to psychology experts:
Light and playful conversation starters
Childhood and memories
Questions about childhood experiences are universally relatable and often spark nostalgic stories. Ask about their favorite childhood memory, what they wanted to be when they grew up, their favorite toy, or their most embarrassing moment from school. These topics feel safe yet personal, allowing you to learn about their background while sharing your own experiences.
Passions and hobbies
Rachel Moheban Wachtel, licensed marriage therapist, says that picking up on a person’s specific interests is key to getting them to open up to us. Because in a way, we’re all our best and truest selves when we talk about the things that really interest us and spark our passion.
So you can ask: “What’s your favorite way to spend your time?”, “What would you do with an extra 10 hours a week?”, “What would be the topic of your New York Times bestselling book?”, and “What do you love learning about and why?” Just be sure to show curiosity and encourage them to talk more about it to really deepen the conversation.
Lifestyle and preferences
Fun lifestyle questions reveal personality without being too intense. Try asking whether they’re a morning person or night owl, their ideal weekend, favorite comfort food, or if they prefer spontaneous adventures or planned activities. These topics help you understand their daily rhythms and preferences.
Work or studies
Now, if you don’t know the person that well yet, try asking them about their work or studies. Although most people might feel that questions like these are boring and generic, according to psychotherapist Dr. Joe Sanok, these topics can be great conversation starters, too. Because if you’re still getting to know your crush, it’s better to start with small and simple to gradually build comfort, trust, and depth in your relationship.
And make it more interesting by asking things like, “Have you been working on any cool projects lately?”, “Did anything interesting happen at work/school today?”, and “What’s it like working in this certain company/going to this certain school? What do you like about it?”
Travel and adventure topics
Dream destinations
Travel conversations often reveal someone’s sense of adventure and values. Ask where they’d go if money wasn’t an issue, their best vacation memory, or the most unusual place they’ve visited. These questions can lead to sharing travel stories and future aspirations.
Hypothetical adventures
Engage their imagination with questions like “If you could live anywhere for a year, where would it be?” or “What’s the most adventurous thing on your bucket list?” These topics allow for creative responses and can reveal their risk tolerance and dreams.
Pop culture
If you’re still testing the waters and keeping things casual with your crush, talking about pop culture can be a great way to get them to warm up to you and get to know them better. Just skip the usual cliches and phrase your questions in a more interesting way.
An article for PsychCentral, written by health and wellness journalist Hilary Lebow and reviewed by therapist Dr. Jennifer Litner, has a few good examples you can borrow like: “If you could be best friends with any famous person, who would it be?”, “What books/movies/albums have had the biggest influence on you?”, and “Which fictional character do you like/relate to the most?”
Values and personality deep-dives
Life philosophy
Once you’ve established rapport, transition to questions that reveal deeper values. Ask about their definition of success, what makes them feel most grateful, or the best advice they’ve ever received. These conversations help determine compatibility beyond surface attraction.
Themselves
Another great strategy you can try your luck with is getting your crush to talk more about themselves by asking thought-provoking, open-ended questions. For example: “What’s your favorite thing about yourself?”, “How would your closest friends describe you?”, “What does the perfect day look like to you?”, “What would be the title of your memoir?”, “What’s your dream vacation?”, and “What are the experiences that shaped you the most as a person?”
Questions like these work because, according to professional marriage and family therapist Kimberly Panganiban, the goal of every good conversation is to learn new things about one another and personal questions such as these can help bring about the deepest connection.
Personal growth
Similar to our earlier point, you can ask the other person about their personal growth to make the conversation more engaging. Just be sure that you’re both at a place where you’re really ready to be vulnerable with one another. “Sharing from a pace of vulnerability is how to truly get to know someone,” says Dr. Megan Fleming, clinical psychologist and sex therapist. “Connecting with others is all about our willingness to be truly seen, which comes from sharing our most embarrassing, challenging, and often most difficult moments.”
So try your best to keep it positive and show empathy when you ask your crush things like: “What’s your biggest achievement so far?”, “What personal accomplishment are you proudest of?”, “What’s the best way life has surprised you?”, and “What are you most thankful for right now that you didn’t have before?”
Flirty and connection-building topics
Romantic preferences
When the conversation naturally progresses, you can explore romantic topics. Ask about their love language, ideal date, what they find attractive in a person, or their thoughts on relationships. These questions signal romantic interest while gathering important compatibility information.
Playful hypotheticals
Light flirting can happen through fun scenarios like “If you could have any superpower, what would it be and why?” or “If we were watching a movie together, what would you choose?” These questions maintain playfulness while creating shared imaginary experiences.
Creative and imaginative topics
Entertainment preferences
Discussing books, movies, music, and shows reveals shared interests and different perspectives. Ask about the last book that impacted them, their go-to karaoke song, or what show they’re currently binge-watching. These topics often lead to recommendations and future conversation material.
Hypothetical scenarios
Creative questions like “If you could have dinner with any three people, who would they be?” or “What would your theme song be if you had one?” encourage imaginative responses and reveal their interests and values.
Building deeper connection
Family and relationships
Once you’re comfortable with each other, ask about family dynamics, how they met their best friend, or what they learned from past relationships. These topics provide insight into their relationship patterns and emotional intelligence.
Future aspirations
Discussing goals and dreams helps assess long-term compatibility. Ask about their career aspirations, where they see themselves in five years, or what legacy they want to leave. These conversations can reveal shared values and life directions.
Conversation flow tips
Whatever topic you choose to go with, just keep in mind these important tips from Kendra Cherry, psychology writer and educational consultant for VeryWell Mind, in mastering the art of conversations: ask interesting, open-ended questions; get a good feel for what’s appropriate to the context/situation (e.g., if they’re ready to get deeper or if it’s better to keep the tone light for now); strike a balance (e.g., making small talk before getting heavy, or sharing your own answers, too); and always convey interest, engagement, openness, and friendliness as best as you can.
The most important aspect isn’t the specific question you ask, but how you engage with their response. Show genuine interest by asking follow-up questions, sharing your own related experiences, and maintaining active listening. Remember that great conversations are built on mutual curiosity and authentic interest in getting to know each other.
Start with lighter topics and gradually progress to deeper subjects as comfort builds. The goal isn’t to interview your crush but to create a natural flow where both of you feel heard, understood, and excited to continue the conversation. Focus on finding common ground while appreciating your differences, and let your genuine enthusiasm for learning about them guide the discussion.
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