101 Online Dating Questions to Ask

|Whether it’s your first phone call or first date

Online dating questions are best when they’re open-ended, so you can get to know this brand-new person who might (if all goes well) become a huge part of your life.

But timing is everything. (So is tact.)

There’s an art to when to ask different types of questions, based on where you are in the relationship and how the conversation is flowing. You don’t want to come across as creepily eager by immediately asking “Soooo, do you want kids someday?”

Since it’s 2022, you’re probably going to start chatting via dating app messaging, then texting, and then your first online date will likely take place over the phone (to see if you like each other enough to meet in person).

(Pssssst! We’re big safety sticklers, here at Hushed, so please consider using a temporary phone number when you’re initially texting and calling with someone you met online dating. Using a temporary, anonymous phone number helps protect your privacy, and makes it much easier to cut ties if the person turns out to be hella awful.)

It’s natural to be nervous when you’re first chatting with someone you’re online dating, so whether it’s your very first phone call (eeek!) or your first in-person date (!!!), we’ve put together a massive list of online dating questions so you can choose your favorites and ask what feels most comfortable.

Ready to play 20 Questions? (Okay, more like a zillion questions.)

Here are 101 questions you might want to ask when online dating …

The Basic Online Dating Questions

When the first date begins, you’ll want to start off with nice, light questions. Unless you’re at a speed-dating event, there will be plenty of time to dive into deeper topics later on. For now, stick with these safe openers …

  • “How was your day?”
  • “How did you choose this place?” (or “Where would we be right now if we were meeting up in person?”)
  • “What’s your favorite thing to order here?” (“What are you wearing right now?”)
  • “What made you want to set up this date?”
  • “What were you thinking, leading up to this date?”
  • “What stood out about my online dating profile?”
  • “Have you been online dating long?”
  • “Which dating apps do you use?”

The ‘Everyday Life’ Online Dating Questions

When you’re getting to know someone, it’s helpful to know how they actually spend their time. (After all, their online dating profile might have made it sound like they do nothing but go fly-fishing and walk on the beach.) So here are a few questions will help you get to know what their everyday life is like …

  • “What did you do last night/last weekend?”
  • “What does an ideal weekend look like?”
  • “What are your friends like?”
  • “What do you do for fun?”
  • “Tell me about your hobbies? …”
  • “Do you have a passion project?”
  • “Are you outdoorsy or indoorsy?”
  • “How do you unwind after a hard day?”

The ‘Favorites’ Online Dating Questions

You’re doing great! Now you can move on to another set of easy questions. Everyone loves to talk about their favorite stuff, and you might be sitting in a bar or restaurant right now for this date. It’s the perfect chance to chat about what they like (and don’t like) …

  • “What’s your favorite sports team?”
  • “Where was your last vacation?”
  • “What’s been your favorite vacation?”
  • “What’s your dream destination?”
  • “What’s your favorite food?”
  • “What’s your favorite drink?”
  • “Favorite take-out order?”
  • “What’s a food you hate/won’t eat?”
  • “Favorite ice cream flavor?”
  • “What’s your current obsession?”
  • “Favorite event to watch in the Olympics?”

‘Multimedia’ Online Dating Questions

This category is easy. You’ve probably watching enough movies about online dating to know that people on dates love bantering back and forth about nice, safe topics like their favorite TV shows, books, movies, etc.

  • “What’s your all-time favorite movie?”
  • “What are you watching right now on Netflix?”
  • “What’s your go-to TV show to rewatch?”
  • “Who is your favorite actor/actress?”
  • “What’s your favorite band?/Who’s your favorite musical artist?”
  • “Best concert you’ve ever been to?”
  • “Who would you love to see in concert?”
  • “Do you have a favorite book/author?”
  • “Most-used app on your phone?”
  • “Most-visited website?”

‘Backgrounder’ Online Dating Questions

As you get to know your date, the conversation will naturally want to go backwards. Backwards in time, that is. People are always curious about where other people come from, and what their family deal is …

  • “Are you from here originally?”
  • “Where did you grow up?”
  • “What made you decide to move here?”
  • “What were you like as a kid?”
  • “Tell me about your family …”
  • “Are you a big family person?”
  • “Do you have any siblings?”
  • “Are you close with your sibling(s)?”
  • “Where does your family live?”
  • “Where did you go to school?”
  • “What were you like in school?”
  • “What did you major in?”
  • “Do you have any pets?”
  • “Can I see a picture of your pet(s)?”

Career-Focused Online Dating Questions

Don’t hover too long on the career category, even if their job happens to be super interesting (although it probably isn’t). You don’t want your date to feel like a job interview, but it’s a good idea to ask a question or two about how this person makes a living …

  • “Tell me about your job …”
  • “How long have you been in this role?”
  • “What does a typical day look like?”
  • “Do you like what you do?”
  • “Do you work with nice people?”
  • “What’s next for you at work?”

Introspective Online Dating Questions

Yup, we think you’re ready. By this point in the conversation, you can start asking something a little more intimate. Some of these questions might open up fascinating new topics, sprinkled with nostalgia and maybe the odd emotional tear.

  • “What are you looking forward to, right now?”
  • “Who’s the most special person in your life?”
  • “What’s something most people don’t know about you?”
  • “What’s one of your favorite childhood memories?”
  • “What’s on your bucket list?”
  • “Are you an extrovert or an introvert?”
  • “What was the happiest moment of your life so far?”
  • “What’s your favorite place in the world?”
  • “Would you want to be really, really famous?”
  • “What’s your favorite holiday?”
  • “Best advice you’ve ever gotten?”
  • “What would you try if you knew you couldn’t fail?”
  • “What are your long-term goals?”
  • “What’s the best present you’ve ever given?”
  • “What’s the best present you’ve ever received?”
  • “If you could give someone one piece of advice, it would be …?”
  • “What’s the most spontaneous thing you’ve ever done?”
  • “If you could have dinner with anyone in the world, who would it be?”
  • “What’s an expensive splurge, but totally worth it?”
  • “What would you do if you won the lottery?”
  • “What would you do if you didn’t need to have a job?”

Romantic Online Dating Questions

You don’t want to come across as a stalker, but you do want to casually ask a few things to figure out what you’re getting yourself into, right? Don’t ask all of these (they might go running for the nearest exit), but here a few suggestions to drop in the conversation …

  • “What’s the worst date you’ve ever been on?”
  • “Who’s your celebrity crush?”
  • “What was your longest relationship?”
  • “Have you ever had your heart broken?”
  • “Tell me about your ideal partner …”
  • “Would you say you’re a romantic?”
  • “What’s the best dating/love advice you’ve ever received?”
  • “What do you like about being in a relationship?”
  • “What do you dislike about being in a relationship?”
  • “What’s your biggest pet peeve when you’re dating someone?”

‘Big Picture’ Online Dating Questions

Warning! Do not approach the following potentially-loaded questions unless you’re (A) determined not to waste your time with someone who’s values don’t align with yours, or (B) delighted by asking questions that might make a near-stranger really uncomfortable.

  • “Are you looking for a relationship?”
  • “What are you looking for in a serious relationship?”
  • “Do you want kids?/Do you ever think about having kids?”
  • “How many kids would you want?”
  • “What kind of parent would you want to be?”
  • “What’s your opinion on marriage?”
  • “What would stop you from pursuing marriage?”
  • “How do you plan to vote in the next election?”
  • “How religious are you?”

The ‘Next Steps’ Online Dating Questions

Best not to end the night with “What’s your favorite food? … Okay, bye.” So here are a few tantalizing questions you can ask at the end of your date if you’d like to have another date (and you hope they do, too) …

  • “Should we have a second date?”
  • “Can I kiss you?” (or “If we were in the same room right now, would you want to kiss me?”)
  • “How do you think this date went?”
  • “Is there anything you want to ask me?”

Good luck with your date, whether it’s taking place over the phone or in person.

And please remember to protect your privacy with a temporary phone number, so you don’t expose too much personal information until you’re confident you’ve met The One.