The secret to making someone like you isn’t about impressing them with stories or bragging about yourself—it’s about asking the right questions. People naturally enjoy conversations where they feel heard, valued, and emotionally engaged. When you ask thoughtful questions, you show genuine interest, spark meaningful discussions, and create a sense of connection. The key is to avoid generic small talk and instead ask open-ended questions that encourage deeper conversation. By steering away from yes-or-no questions and diving into topics that reveal personality, humor, and shared experiences, you create a lasting impression. Whether you’re on a first date, networking, or simply trying to build rapport, these questions will make you instantly more likable. Here are the best questions to ask during a conversation to make someone feel good—and make them like you more.
1. “What’s something you’re really passionate about?”
People love talking about their passions, yet many conversations never touch on what truly excites them. When you ask someone what they’re passionate about, it allows them to share something meaningful. It shifts the conversation from small talk to personal interests, creating a more engaging and memorable exchange. Passionate topics also reveal a person’s values, dreams, and what truly makes them happy. According to countryliving.com, a solid icebreaker can get the conversation going right away.
Instead of just asking about their job or routine, this question opens the door to deeper discussions. Pay attention to how their face lights up when they talk about something they love—it’s an instant way to build a connection. When you show genuine curiosity about their interests, they’ll naturally associate positive feelings with you.
2. “What’s the most unexpected or crazy thing you’ve ever done?”
People love sharing exciting stories, and this question encourages them to recall fun, adventurous, or even embarrassing experiences. It helps break the ice and brings energy into the conversation. Whether it’s a spontaneous trip, an unusual encounter, or an impulsive decision, this question invites storytelling and laughter. Sharing wild or unexpected moments also reveals personality and a sense of humor. According to wondermind.com, asking about the most adventurous thing someone has ever done is a good way to get to know someone better.
This type of question also creates an opportunity for you to share a fun story of your own. By exchanging experiences, you establish a sense of familiarity and camaraderie. When a conversation feels playful and spontaneous, it naturally makes both people feel more connected.
3. “What’s a small thing that always makes your day better?”
This question shifts the focus toward positive emotions and personal joys. It encourages the other person to reflect on the little things that bring them happiness, which instantly puts them in a good mood. Whether it’s a favorite coffee order, a morning routine, or a funny meme, small joys give insight into what makes them tick. According to parade.com, asking someone “What made you smile today?” is a good conversation starter.
Understanding someone’s simple pleasures also makes it easier to form a bond. If you learn what makes their day better, you can use that knowledge later to strengthen your connection. People remember those who make them feel good, and asking about their daily happiness builds warmth and comfort in a conversation.
4. “If you could instantly master one skill, what would it be and why?”
This question taps into someone’s aspirations and hidden interests, making the conversation more engaging. It allows them to dream a little, share a personal goal, or even reveal a quirky talent they’ve always wanted to have. Whether they wish they could play an instrument, speak a new language, or be a pro athlete, their answer gives you a glimpse into their personality. According to today.com, asking someone about the one person, living or dead, who they would want to get coffee with is a good conversation starter.
It also creates an opportunity for a playful discussion about self-improvement and what fascinates them. If you both share a similar desire to learn something, it can spark deeper conversations about growth and experiences. People enjoy discussing their ambitions, and this question makes you more memorable by showing that you’re genuinely interested in their dreams.
5. “What’s one thing you wish more people knew about you?”
This question invites someone to open up in a way that feels safe and intriguing. It gives them a chance to share a side of themselves that others might not usually see. Some people may talk about an underrated skill, a hidden talent, or a part of their personality they feel goes unnoticed.
By asking this, you show that you want to understand them beyond surface-level impressions. It can lead to meaningful discussions and help build trust in a short amount of time. When people feel truly seen and appreciated, they naturally form a stronger connection with the person who took the time to ask.
6. “What’s the funniest or most embarrassing thing that’s ever happened to you?”
Humor is a powerful way to build attraction and make conversations enjoyable. This question allows someone to share a funny or awkward moment, which makes the interaction more relaxed and entertaining. Laughing together creates an instant bond, helping both of you feel more comfortable.
Additionally, sharing embarrassing stories shows confidence and self-awareness. If you’re willing to laugh at yourself, the other person is more likely to feel at ease around you. A lighthearted, funny conversation makes you more likable and keeps the energy fun and positive.
7. “What’s a childhood memory that still makes you smile?”
Nostalgia brings out deep emotions, and this question invites someone to share a meaningful or joyful experience from their past. Recalling happy memories often triggers positive emotions, making them feel good during the conversation. It also gives insight into their upbringing, values, and what shaped them into the person they are today.
This type of question creates an opportunity for storytelling and mutual connection. If you find similarities in your childhood experiences, it instantly strengthens your bond. The more positive emotions you create in a conversation, the more the person will associate those feelings with you.
8. “If you could relive any day in your life, which one would it be?”
Asking this question allows the other person to reflect on their most cherished moments. Whether it’s a special trip, a major accomplishment, or a perfect day with loved ones, their answer gives you insight into what truly matters to them. It also deepens the conversation, as people enjoy reliving their happiest experiences.
It’s an emotional and thoughtful question that makes people feel seen and understood. When someone talks about a moment that holds meaning for them, they form a stronger connection with the person who listens. Asking about past happiness makes future conversations feel even more meaningful.
9. “If money or time weren’t an issue, what would your dream life look like?”
This question encourages someone to open up about their biggest aspirations without limitations. It gives them permission to dream big and share their ultimate vision for their life. Whether it’s traveling the world, starting a business, or pursuing a creative passion, their answer reveals what truly excites them.
It also provides a natural transition into discussing future goals, ambitions, and shared dreams. If your visions align, it creates a sense of connection and possibility. Even if your goals are different, this question leads to engaging discussions about adventure, success, and what makes life fulfilling.
The best conversations don’t just exchange information—they create emotional connections. Asking thoughtful, engaging questions makes people feel valued and understood, instantly making you more likable. When you make someone feel good in a conversation, they will naturally be drawn to you. Whether you’re on a date, meeting new friends, or networking, these questions will help you build deeper relationships effortlessly. Keep the conversation flowing, be genuinely curious, and watch as people naturally gravitate toward you.
