- Ask about their ideal weekend and favorite shows and music to see if your interests and lifestyles are compatible.
- Find out if your values align by asking about their goals, passions, and role models.
- See if your physical connection is a match by asking about their ideal date and turn-ons.
- Spark a funny conversation with a game of “Would you rather.”
“What’s your favorite movie, TV show, or book?”
Get your conversation started by asking about their favorite things. They might prefer fantasy shows while you’re a die-hard sci-fi fan, which can lead to a really fun and engaging conversation! Plus, this can give you insight into what they’re interested in. Asking questions back-to-back can often come across like an interview. To have a more natural, free-flowing conversation, dive deeper into a single topic. Asking why it's their favorite movie can lead to a conversation about their passions, childhood experiences, and personal beliefs.
“Why’d you swipe on my profile?”
Ask why they swiped to see if they want a serious or casual relationship. This is a flirty way to ask why they’re on Hinge or Bumble and can help you weed out incompatible matches. If you’re looking for a thoughtful, serious relationship and your match just compliments your looks, this might hint that you’re not looking for the same things. If they ask you this question back, be thoughtful about why you matched with them. People can usually tell if you’re giving a copy-paste answer. Look at their profile answers and pictures to pick out things that drew you to them and that you are curious to learn more about.
“What do you usually get up to on the weekend?”
Their ideal weekend can reveal if your lifestyles are compatible. If you’re looking for someone who wants to grab brunch then go thrifting, this will help you find them. Plus, it’s a more fun question to ask than the standard, “What do you like to do to have fun?”
“What songs do you like to blast with the windows down?”
See if their music taste vibes with yours. This is another easy conversation opener that can tell you about your match’s likes, dislikes, and personality. Are they down in the mosh pit at every music festival? Or maybe you’re more likely to catch them at your local music hall jamming to Beethoven. For less open-ended questions like these, it’s a great idea to ask “Why?” This helps the conversation flow and can give you a better idea of who they are.
“What’s your favorite restaurant in town?”
The foods and flavors they like can tell you more about who they are. Maybe they prefer the comforts of home and simply enjoy a great slice of pizza. They might like the nightlife scene and trying the hottest new restaurants in your city. Or, they could be an adventurous eater who knows all the best hole-in-the-wall spots. If you’re looking to date, use the app to meet your matches in person! Once you’ve established that you’re interested, you can easily ask your match on a date by following up their answer with “So, can I take you there sometime then?”
“Do you have any hidden talents?”
Asking about their quirks or talents can help draw you closer. As you’re asking about a hidden talent, it’s likely that they’re trusting you with information that most people don’t know. This question can then lead to a funny conversation about embarrassing stories and childhood hobbies that will tell you more about them.
“What’s a typical day in your life like?”
Get an idea of their daily routine and what’s important to them. This can tell you more about who they are and what they value outside of work. They might be big on exercise and wake up at the crack of dawn to go to the gym. Or, they might be a foodie who relaxes after a long day at work by cooking an elaborate meal.
“Do you have any pets?”
How they feel about pets can be a clear deal breaker. For lots of people, their furry friend is like their family. If you have a pet and your match isn’t into animals, this can be a sign that things won’t work out. On the other hand, if you’re both obsessed with your pets, you can start a fun conversation about their cute quirks.
“What’s something you love but other people hate?”
Find out if your match holds any controversial opinions. While this can be a funny icebreaker, their opinions can reveal a lot about what they believe in. Whether that’s something you can laugh about, like pineapple on pizza, or something that’s important to you that they disagree on, will tell you if your match is worth pursuing.
“How would your friends describe you?"
Get an objective description of what your match is really like. “Tell me about yourself” can get overused and tired, while this question allows your match to reflect on their key traits. Plus, you can get some insight about their friends with this question, or easily segue to asking about them! A fun follow-up question is asking if they think their friend’s description is accurate. If it isn’t, ask them why not.
“What do you hope to accomplish in the next 5 years?”
See how your personal and professional goals align. Whether you’re a career-driven go-getter or taking life one day at a time, you’re probably looking for someone who shares similar attitudes and values to you. This question will also tell you more about who they are. They might be a creative who is planning to take off their photography business in the next 5 years. If they’re family-oriented, they might be hoping to start a family soon.
“Are you close with your family?"
Family dynamics and values have a huge impact on who they are. Who they were raised by, whether they have siblings, and how often they see their family can tell you a lot about their background and why they are the person they are today. While it’s okay if you don’t have the same type of relationship with your families, it’s a good idea to figure out if your beliefs and values match. Ask this question after you’ve gotten to know your match better. Families can be sensitive and complicated, so you want to save this once you are comfortable and more vulnerable with each other.
“What was your favorite movie, book, or toy as a kid?”
Their childhood favorites can tell you what they were like as a kid. This simple question can open up a conversation about their childhood hobbies, what it was like growing up, and who their friends were. It’s natural to be curious about what your match was like as a kid, because their childhood can tell you more about who they are today and what’s important to them.
“What do you like most about your job?”
Find out what drives and motivates them in their career. Do they love their job because it gives them financial security to pursue their hobbies? Or, are they proud that they help a lot of people with their work? This can give you a better idea of what’s important to them and what they’re passionate about. Keep the conversation going by asking how they got into their line of work. If you want to get deeper, ask if it’s their dream job or if they see something else in their future.
“Who is your role model?”
Who they admire can show you the values that are important to them. To make a potential relationship work, you and your match need to share compatible beliefs about life and work. If you're a tech-savvy business person and your match is inspired by Steve Jobs, that might tell you that they’re also hardworking and dedicated to their job. This can also be a great question to highlight any relationship deal breakers or potential red flags. If your match is influenced by someone who goes against your beliefs or values, they probably aren’t compatible with you.
“What’s something you’re really passionate about?”
See what causes and topics make them light up. It’s no secret that people love talking about their passions, so this is a great question to ask as you’re getting to know your match. Their passions can reveal what’s important to them and tell you more about their hobbies. They might be a runner and complete charity marathons, or love reading and volunteer at their local library.
“What’s something you’re really proud of?”
Find out what accomplishments and moments in their life are important. This question lets your match show off to you and can spark a deeper conversation about their background and beliefs. As this can lead to a more meaningful conversation, wait to ask this once you’ve gotten to know them better.
“What are your relationship deal-breakers?”
See if there are any qualities that make you incompatible. After getting to know your match, ask them about what they want and need in a relationship. It’s best that you’re upfront about a potential relationship working between you two before you invest time in something that isn’t likely to go anywhere long-term.
“What are you looking for in a relationship?”
Be direct and ask what your match is looking for in a partner. This is a great question to ask them in the beginning to see if you want the same things out of a relationship. Are they on OKCupid just to chat or to find a friends-with-benefits situation? Or maybe they’re moving soon and looking for a serious partner who is open to long-distance.
“When was your last relationship?”
Their dating history can tell you more about what they’re looking for. Past relationships can be a sensitive topic, so don’t talk about your dating history right off the bat. Wait until you and your match are more vulnerable with each other and talking about deeper topics. Sharing your histories can bring you closer and help solidify your connection.
“What does the perfect date look like to you?”
Ask them to plan a date to see what they’re like in a relationship. This can be a flirty question to ask that also gives you great information on how they show their love. If you like their idea of romance and are sure that you and your match have chemistry, this question can easily segue into asking them on a date. When you ask a match out on a date, keep it simple and direct. Say something like, “Hey, I think we have a lot in common and I’d like to meet you in person. Are you free for dinner next week?”
“What’s the worst date you’ve been on?”
Start a funny conversation and find out what not to do on a date. This is a more light-hearted way to ask about their past relationships that can lead to a funny conversation about their experiences on Hinge, Bumble, or Tinder. If you’re ready to get deeper with each other, it can also spark a conversation about their relationship history.
“What do you like better: kisses or cuddles?”
Physical chemistry is just as important as your emotional connection. Asking flirty questions about how they like to be intimate can tell you if your ideas of romance are compatible. Then, you can naturally deepen the conversation by asking about their turn-ons and offs. You don’t want to ask this question right off the bat as it can come off too strong. Unless you and your match are upfront about only wanting a physical connection, wait until you have a solid conversation going before getting into more intimate topics.
“What makes you laugh?”
Laughter and a sense of humor are important in a relationship. See if your chemistry extends to what you each find funny and whether you can make each other laugh. Send along your favorite joke, meme, or video and see if the sparks fly!
“What’s your most embarrassing moment?”
Get comfortable with each other by asking about an embarrassing story. This will more than likely lead to a lively, funny conversation where you get to learn more about their experiences. Plus, it's a great way for them to show off their sense of humor and see if they can laugh at themselves.
“If you won the lottery, what’s the first thing you’d buy?”
How they’d spend a fortune can tell you about their interests. Get to know you questions definitely don’t have to be serious! Asking fun, open-ended questions like this can start a really engaging conversation that organically leads to other topics that tell you more about your match.
“You wake up with a superpower. What is it?”
Start an engaging conversation about their superhero fantasies. This is a fun icebreaker conversation to have because most people have dreamt about having powers at least once in their life. As a bonus, the superpower they choose might tell you more about their personality.
“If you could travel anywhere in the world, where would you go?”
Find out where they want to travel and vacation to. This is another great question to ask your match as you’re getting to know them. It can reveal where they’ve been before and open up a conversation about their experiences. Plus, it can tell you if they have an adventurous spirit or prefer cozying up on the couch and staying in.
“How would you describe yourself with 3 emojis?”
Be playful when you ask them to describe themselves. This is a less serious and way more fun way to get your match to explain who they are. Once they’ve sent their emojis, ask them to explain their choices. You’ll likely laugh about the emojis you each chose and what they mean to you.
“Would you rather jump or skip instead of walking?”
Get to know them better with a funny game of “Would you rather.” There’s nothing better than sending them a random question and seeing how they react. It’s a great way to see how they think and spark a funny conversation about why they think one option is better than the other. Get them laughing with other questions like: “Would you rather live on the moon or under water?” “Would you rather travel to the past or the future?” “Would you rather have to whisper or shout when you talk?” “Would you rather be 20% smarter or 20% more attractive?” “Would you rather only be able to listen to music or watch TV?”
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