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18 GOOD ONLINE DATING QUESTIONS TO ASK GIRLS & GUYS

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. The most important part of keeping conversation going on online dating, is by asking your match a good question. 

Some people are just good at that as they are good conversationalists. They just notice certain details, remember names, and never seem to have a loss for words. Well, at least that is what my friend was like. He was someone I could have a six hour chat with without the topics getting boring and dry. Once he asked me, “What do you like best about me?” And I thought for a moment before answering, “You ask good questions.” And yes, I was completely sincere. 

Asking a well thought out or original question is an attractive quality to online daters. Getting new original questions is always exciting, as online daters quickly grow tired of vague questions like “How are you?” and “How was your day?” On a dating site. 

When you meet someone online, your questions and conversations are what’s creating the spark. To help you connect on the online dating world and to keep the conversation following with a possible match, we’ve highlighted 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. Use this to find the words to attract someone and make a genuine connection online. 

Good Online Dating Questions to Ask Girls (#1-9)

We don’t always know what type of question to ask our match 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?”

You know how they say that no question is a wrong question. Well, in this case there are certain types of wrong questions or inappropriate questions to ask your online dating match. 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). 

Our top nine questions to ask girls focus on personality traits, not sexual positions. If you want to keep her interest, keep it clean fellas. 

1. What Are Your Life Goals? What Motivates You to Get Up in the Morning?

This is a really good opening question to ask a girl on online dating because it’s open-ended and personal. For a woman, her goals and motivations are very important to who she is. You can not go wrong to ask a woman this question, and she’ll probably have a lot to say on the subject.

This was in fact the question which led me to realise that I want a future with my now current boyfriend. That question sparked a full-blown conversation about what we’re both looking for, not just in relationships, but in life.

2. What’s Your Favourite Movie/Book/TV Show/Band?

To ask someone about their favourite things is a pretty standard question to break the ice between you and your match online. Although it is not exactly original and personal, it is still a good starting point for a conversation. And who knows, maybe she likes the same things as you. But to ensure that you keep that conversation flowing without getting boring, you need to ask a decent follow up question like, “What do you like about it/them?” or “Who’s your favourite character/band member?” 

Believe it or not, but people actually always like talking about their favourite things.

3. Who’s Your Biggest Role Model in Life?

This is a good general question to ask a girl online. Everyone has someone they admire. Whether it is Beyoncé, or their mother, these influential figures are important to your date for a reason. If you really want to connect with your date, that the type of questions to start with. It shows that you care about knowing who she is and what makes her. 

4. What’s Your Most Bizarre Talent?

For those looking to go outside the standard routine and go for the more playful routine of questioning and getting to know the goofy side of the other person, this question is for you. 

You might just find out some weird stuff about your online date by just asking this question, but it’s sure to give you and your date a good laugh.

5. Do You Like Beer, Wine, or Cocktails?

This is a good start-up question to get to know what your date likes or dislikes. A girl will always be impressed if you remembered her type of drink while on a date. It’s simple, but it works. Once you know what your crush likes to drink, you can make a personalised date suggestion to them. If they like wine, you can ask them out on a wine tasting tour. And for interests sake, according to OkCupid, online daters who like the taste of beer are more likely to have sex on the first date. Good to know.

6. Who’s Your Best Friend & What’s He/She Like?

If you guy’s haven’t figured it out by now, if you’re hoping to date the girl, you need to win over her best friend. This is a solid strategy for guys to get to know the girl online. You can learn a lot about your date through knowing who her friends are and what type of relationships and people she attracts to. Plus, you will score some brownie points from the best friend when your online date inevitably tells her you asked about him/her.

7. What Were You Like As a Kid, or Where Did You Grow Up?

For anyone in search of the perfect online dating question that will really show you care and ready for something more deeper to connect to, 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, princesses and fairytales. Those memories that she will be sharing with you are likely some of the most dearest to her heart. That is the type of memories that can tell you a lot about her personality as an adult.

8. What Accomplishments Are You Most Proud of?

All online daters have seen all the grandstanding and showboating on dating websites. Yes males have always displayed their accomplishments and achievements as an attempt to impress woman. Have you ever asked a woman to brag about her accomplishments as she should?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. You will get to know the ambitious side of a person. Who knows? You could be talking to 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 at the moment in life?” You will get to know a lot about a person in the career he or she chose. If she’s studying, ask her what her major is, why she chose that major, and what she would like to leave behind in that career path? 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. These questions will also spark some interesting conversations as it will get both you and your partner thinking.

Good Online Dating Questions to Ask Guys 

Men are pretty much open to any question and don’t tend to be too squeamish about chatting with girls online. Where women on dating websites and apps response rate differ. According to Business Insider, on average, men have to send 25 messages to get one response, while women only have to send five.

The focus for female online daters isn’t so much about attracting a guy but rather attracting the right guy. And to try and narrow that part down and find our compatible match woman ask pointed questions. If you want to find out who someone is, ask a few good questions about their past experiences, present interests, and future ambitions.

Always be sure that its a question that you are willing to answer as well, as it’s probably going to be asked right back to you. Be sure to have your own answers ready.

10. What’s Your Ideal Saturday Activity?

For practical purposes, this is a good question to ask your online date. It is good to know what his idea of a Saturday is because chances are its is going to influence what type of date activities come into play. This is an important type of question to ask when getting to know a guy online because it is important to make sure you sync up on your ideas of fun.

My ideal Saturday is relaxing around with my cat while being a little artsy craftsy and maybe watching Netflix. If a guy tells me he loves to play with his parrot and run marathons (not on Netflix), I sure we’re going to have  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. I am personally a very huge family person and it is always fun talking to someone who can relate. The way a person talks about his siblings and family can give you clues to his personality and just what type of man he is. For example, I’m always drawn to guys who feel protective of their little sisters because they’re often more gentlemanly on dates, but also because I have an older brother who has always been protective over me.

According to matchmaker and dating expert Sarah Patt, “If they are talking about their family, it shows they have great relationships with their parents and siblings.”

12. Do You Know What Your Calling in Life Is?

This is a slight deeper question to ask your online date than asking him about his 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. 

13. What’s Something You Could Talk About for Hours?

I would say this is the easier question to ask your online date. With this question, you’re basically inviting a person to pick their favourite topic of conversation which you could then elaborate on. And as we said, everyone love talking about their favourite things. You never know what the topic might be. You might be surprised on how interesting it is or exactly the same as yours. Once you find what your crush are interested in, topics of discussion becomes easier. 

14. What Sort of Vacations Do You Enjoy Most?

It’s always fun to fantasise about exotic destinations and memories of past trips you had. A question about vacations may not seem like a hard-hitting question, but it’s important for long-term relationship seekers. It’s always interesting to hear the fun trips your online crush had. And even talking about what your trip would look like, this way you will get to know more about each other’s interests and likings. 

As Psychology Today has even stated, “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?

A random a fun question like this is an interesting online dating question to ask a guy. It opens the doors to so many stories such as fears, adventures, or making jokes (e.g., “How about sky diving with sharks?”). And if you’re an adrenaline junkie, what better question to put it out there and to highlight your adventurous nature.

16. What’s the Last Movie You Saw in Theaters?

I personally do enjoy the theater, but I really don’t go a lot. Maybe once in a blue moon when a really good movie has been released and I am with the right people. This question is still a must, because who doesn’t enjoy a good movie. Asking this question also tells you what type of movies your date likes and how often he goes to the theater. Maybe you can nudge your date into asking you on a movie date. 

17. Do You Have Any Tattoos/Scars?

Yes, this question might be a bit foward, but it is a good conversation starter. Guys are typically more than willing to talk about a favourite tattoo or a grisly scar. If you have noticed a tattoo or a scar on a picture on your crush’s profile, then go ahead and ask him. It will undoubtedly lead to a good story.

18. Do You Prefer the People in Your Life to be Simple or Complex?

Yes this may seem like a random question, but as everything it has a purpose. 

If you agree that this question has a purpose, 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?”

Although many online daters think it’s impolite to discuss politics too early on, there’s no rule against asking about simple versus complex people. 


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