My last boyfriend was a solid conversationalist. He noticed details, remembered names, and never seemed at a loss for words. Once he asked me, “What do you like best about me?” And I thought for a moment before answering, “You ask good questions.”
He thought I was joking, but I was completely sincere. Asking an original or thoughtful question is an attractive quality to daters, especially online daters who quickly tire of vague questions like “How are you?” and “How was your day?” On a dating site, a more targeted inquiry like “What are your pet peeves?” or “What’s your favorite place in the whole world?” stands out and invites a reply.
When you meet someone online, you have to create a spark through that initial conversation. Good questions are like kindling. If you pile enough on, things really start to heat up. To help you gather tinder to use on Tinder (or any dating site or app), we’ve come up with 18 brilliant questions to ask when online dating. These interesting questions for girls and guys can help you ignite a lively conversation and woo a date.
Questions to Ask Girls | Questions to Ask Guys
Not all guys know what questions to ask a girl when online dating. Some online daters go for something cheesy and playful like “Do you believe in love at first site?” Others try something more probing like “How long was your last relationship?”
And some very misguided guys blunder into inappropriate dating questions. I once got an opening message reading, “Do you like sex?” Hint: That’s not a good question to ask a woman online (or ever, really). It’s presumptuous and creepy. Stay away from sex talk until you’ve built up a rapport with a girl.
Our top nine questions to ask girls focus on personality traits, not sexual positions. Keep it clean, fellas, if you want to keep her interest.
1. What Are Your Life Goals? What Motivates You to Get Up in the Morning?
This is a good opening question for online dating because it’s open-ended and personal. A woman’s goals and motivations are important to who she is, and she’ll probably have a lot to say on the subject. You can learn more about her career, her values, her family, or her dreams in one straightforward question.
Figure out where someone is headed to decide if you want to join them.
“My boyfriend asked me about my ambitions,” said Viv. C in an article on Men’s Health. “That turned into a full-blown conversation about what we’re both looking for, not just in relationships, but in life.”
2. What’s Your Favorite Movie/Book/TV Show/Band?
Asking about favorite things is a pretty standard icebreaker question on dating websites. It’s not exactly original, but it’s a good starting point for a conversation. Just be sure to ask a decent follow-up like, “What do you like about it/them?” or “Who’s your favorite character/band member?” People enjoy talking about their favorite things (just ask Julie Andrews), and you can score bonus points if you’ve watched, read, or enjoyed your date’s favorite stuff.
2. Who’s Your Biggest Role Model in Life?
Everyone has someone they admire, so this is a good general question to ask online daters. Whether it’s Bobby Kennedy, Beyoncé, or a family member, these influential figures are important to your date for a reason. You can find out a lot about a person’s ideals and aspirations by getting them to describe someone they hope to emulate.
4. What’s Your Most Bizarre Talent?
This is a fun question for online daters looking to go outside the standard routine and engage in a more playful line of questioning. You could find out some weird things about your date by asking this, and it’s sure to give you both a laugh. Plus, after she tells you she can juggle beer bottles or walk on her hands, you have a natural opening for a date by replying, “I’ve got to see this in person!”
5. Do You Like Beer, Wine, or Cocktails?
Questions about drinks (or food) are a good way to share likes or dislikes with a date prospect. You can gain her favor by mirroring her drink preferences. It’s simple, but it works. My dad had never tasted Southern Comfort in his life but claimed to love it to please my mom on their first date. It wasn’t a lie, he says, because he was determined to like anything she liked.
By asking good questions, online daters can go from sharing interests to sharing drinks.
Once you know what your crush likes to drink, you can make a personalized date suggestion to them. Like, hey, I heard about a wine tasting down the road, do you want to go? Also, according to OkCupid, online daters who like the taste of beer are more likely to have sex on the first date. Which is just good to know.
6. Who’s Your Best Friend & What’s He/She Like?
If you’re hoping to date a girl, you need to get in the good graces of her best friend. Asking about a bff is a solid strategy for guys. It’s good to learn about that relationship and get some insights into your date by finding out what type of people she gravitates toward. Plus, when she inevitably tells her best friend you asked about him/her, you’ll flatter that all-important person’s ego.
7. What Were You Like As a Kid, or Where Did You Grow Up?
For anyone in search of a good online dating question, this is a reliable choice. We were all kids once, and asking about a girl’s childhood leads to a nostalgic discussion about teachers, toys, and games. The memories she shares with you are likely dear to her heart and can tell you a lot about her personality as an adult.
8. What Accomplishments Are You Most Proud of?
There’s a lot of grandstanding and showboating on dating websites. A lot of guys make all kinds of claims about themselves in an attempt to impress the ladies. Really, though, a great question is more impressive than self-congratulation. Giving a girl a chance to brag on herself is a quick way to make her smile.
If you want to get to know someone, ask about their proudest achievements. Who knows? You could be talking to a world-class chess champion or a viral YouTuber or a proud mother.
9. Do You Like Your Job/Classes/Major?
Another good online dating question for her is, “Do you like what you’re doing right now?” Whatever that may be. If she’s in school, ask her if she likes her school. If she’s working, ask her if she likes her work. Her attitude toward her everyday life is an important consideration for daters, particularly for men who are significantly more likely to rate happiness in women as an attractive quality.
You can ask guys pretty much anything. They don’t tend to be too squeamish about chatting with girls online. Women on dating websites and apps don’t face the same discouragingly low response rates as men do — on average, men have to send 25 messages to get one response, while women only have to send five.
The challenge for female online daters isn’t so much attracting a guy but attracting the right guy. You can do that by asking pointed questions to reveal compatibility. If you want to find out who someone is, ask a few good questions about their past experiences, present interests, and future ambitions.
Online daters can get to know a guy faster by asking the right personal questions.
Just remember, anything you ask is probably going to be asked right back to you. Be sure to have your own answers ready for when they say, “What about you?”
10. What’s Your Ideal Saturday Activity?
This is a good question for practical purposes. If you’re looking to date this guy, chances are his ideal Saturday is going to influence what type of date activities come into play. It’s important to make sure you sync up on your ideas of fun.
For example, my ideal Saturday is lounging around with my dog and marathoning Netflix shows. If a guy tells me he loves to play with his cat and run marathons (not on Netflix), I know we’re going to have some philosophical differences going forward.
11. Do You Have Any Siblings? What’s Your Family Like?
Personally, I’m a fan of the siblings question because it gives you insight into someone’s family life and values. Is he the oldest? Youngest? Middle child? Only child? His birth order and the way he talks about his siblings can give you clues to his personality. For example, I’m always drawn to guys who feel protective of their little sisters because they’re often more gentlemanly on dates.
You can tell a lot about a guy by how he treats his older or younger siblings.
“If they are talking about their family,” matchmaker and dating expert Sarah Patt said, “it shows they have great relationships with their parents and siblings.”
12. Do You Know What Your Calling in Life Is?
This is a bit deeper than asking about someone’s day or hobbies. With one question, you get to the core of a person. Whether or not he’s found his life’s calling, he’s sure to have an introspective response for you to unpack. His inner drive and career ambitions might just line up with your own!
13. What’s Something You Could Talk About for Hours?
With this question, you’re basically inviting a person to pick their favorite topic of conversation and let loose. You never know what someone will come up with in answer. It could be a complete history of trains or a discussion of what’s wrong with the US political system. Once you find what your crush is passionate about, keeping him talking becomes easy.
14. What Sort of Vacations Do You Enjoy Most?
It’s fun to fantasize about exotic destinations and tell stories about past trips. A question about vacations may not seem like a hard-hitting question, but it’s important for long-term relationship seekers. Couples often go on vacations together, so it’s best if their vacation styles match up.
If your date says he enjoys relaxing by the beach, you can start brainstorming sunny vacation ideas.
If you like road trips and your date likes cruises, it’s best to settle those differences from the get-go. To quote Psychology Today, “Vacation preferences or amounts of vacation time can be a major source of ongoing compatibility.”
15. Would You Prefer to Swim With Sharks or Go Sky Diving?
This is an interesting online dating question to ask a guy because it’s so random and fun. It opens the door to telling stories, sharing fears, or making jokes (e.g., “How about sky diving with sharks?”). If you’re an adrenaline junkie, you can highlight your adventurous nature with this type of question.
16. What’s the Last Movie You Saw in Theaters?
This is a must for movie buffs like me. It tells you what type of movies your date prospect likes and how often he goes to the theater. If you enjoy sharing popcorn at the theater with your date, asking this question is a great way to nudge the conversation in that direction. And, of course, you should always follow up with “Did you like it?” or “Who did you go with?”
17. Do You Have Any Tattoos/Scars?
Is the question forward? Yes. Is it a good conversation starter? Absolutely. Guys are typically more than willing to talk about a favorite tattoo or a grisly scar. If you see a picture of a tattoo or scar on your crush’s profile, asking about it will undoubtedly lead to a good story.
Flirtatious daters can ask about tattoos or scars to prod conversations toward physical attributes.
Keep in mind, this online dating question needs the right audience to work best. Straight-laced daters probably won’t appreciate such a racy line of inquiry.
18. Do You Prefer the People in Your Life to be Simple or Complex?
It may seem random, but this question has a purpose. If you agree on this issue, you’ll probably find common ground on political issues as well. According to OkCupid, the answer to this question correlates closely with political ideology. Those who prefer complex people are 65% to 70% more likely to give liberal answers to politically charged questions, including “Should burning your country’s flag be illegal?” and “Should the death penalty be abolished?”
Many daters think it’s impolite to discuss politics too early on, but there’s no rule against asking about simple versus complex people. Using this subtle question, daters can deal with the elephant in the room without invoking controversial topics.
On dating websites and apps, it isn’t hard to find someone to talk to — the trick is figuring out what to say to keep the conversation going. My last boyfriend excelled in that regard, but not everyone has a talent for striking up a conversation with a perfect stranger. If you’re not a natural-born conversationalist, a few good online dating questions can point you in the right direction.
We’ve highlighted the 18 best questions for online dating to help you find the words to attract someone and make a genuine connection online. You can pick your favorites from our list and try them out the next time a profile catches your eye. The right questions can provoke a thoughtful dialogue, give you good insights, and show your date that you care. Any questions?