How to Get to Know Someone Through Online Dating

“Have you done anything fun lately?”

Spice up “How are you?” to be extra playful. This is a great question to ask when you first start talking to someone online because it can start a lively discussion about their hobbies, interests, and friends. Their answer can also help you know if you have similar lifestyles. “Have you gone on any exciting trips lately?” “What’s the best thing you’ve done this week?” “Tell me what you like to do for fun.”

“What’s your favorite thing to do over the weekend?”

Stay clear of “yes” or “no” questions to get to know them better. When first starting to date someone online, it’s best to ask open-ended questions. This way they have to answer with more than one word! Learn more about their favorite activities and hobbies by letting them tell you about them. “What do you like to do in your free time?” “Is there something you can’t not do when you have a day off?” “I noticed your picture of you at the lake with that giant fish. Tell me about that.” Be on the lookout for raunchy pick-up lines. If they sexualize an answer to your question and it makes you feel comfortable, try talking to someone else as their idea of online dating might be different from yours.

“Do you have a favorite movie?”

This common question is a sure way to get to know them. Ask them open-ended questions about their favorite things like movies, food, music, and books. These types of questions are a great way to see if you have common interests. “What’s the best book you’ve ever read?” “Who is your favorite musician?” “What’s one food you couldn’t live without?” Lots of online dating platforms have these questions on their profiles. If an online profile has left these questions blank but says their favorite things are what you’ve filled out in yours, they may be fake or trying to scam you. If you find out that you have some interests in common, talk about that! Reader Poll: We asked 179 wikiHow readers, and 59% agreed that they must have a common interest with someone they’re messaging with online. [Take Poll]

“What was the last show you binged?”

Learn a bit about their interests and home life with this question. Surprisingly, you can tell a lot about a person by what and how they’re watching TV. If they have a 9 to 5 job, chances are they don’t have time to binge watch a whole season of Modern Family. Is their go-to show full of action-packed adventure or reality drama? This is a great way to see if you have common interests and lifestyles. “What’s the last movie you saw in theaters?” “What’s the last book you stayed up late to finish?”

“Are you an early bird or night owl?”

See if you’re compatible with this random question. When you’re online dating, it can be hard to track someone’s schedule when you can message each other whenever you want. This question can help you find out if you’ll vibe with each other’s schedules IRL. “Do you like to stay up late or go to bed early?” “Are you a breakfast for dinner or dinner for breakfast person?” “How many alarms do you have to set each morning?”

“Tell me a little about your family.”

How they talk about their loved ones can tell you a lot about them. This is a question often reserved for the first date, but why wait when you’re online dating? The beauty of online dating is you can go at your own pace, getting comfortable with someone before meeting IRL. So, inquire about their family, pets, friends, and life in general to see if you have the same values. “What do you and your family like to do for fun?” “I saw the cutest dog on your profile! Are they yours?” “How do you and your friends spend the weekend?” There can be a lot of mystery when it comes to online dating. But if they're hesitant to tell you anything about their life, that’s a red flag—they may be hiding something behind their profile.

“Cutest animal? Ugliest animal?”

Get to know them by instigating some fun banter. Propose two questions to your online date and see how they respond. Maybe you both agree that puppies are the cutest animal, but you can’t fathom why they think elephants are ugly! This is a great way to get an idea of their opinions. “Best food? Worst food?” “Favorite plant? Least favorite plant?” “Best fashion choice? Worst fashion choice?”

“What’s the best present you’ve ever received?”

This question can tell you a lot about their personality. Not only will you get some insight on what to possibly get them in the future—fingers crossed things go well—but you’ll learn about their interests. If they cherish a pair of running sneakers their mom got them, chances are they love running. “What’s the best thing anyone’s ever said to you?” “What’s the best purchase you’ve ever made?” “What’s one present you’ve always hoped to receive?”

“Take me on a typical day in your life.”

Get creative with “What do you do?” with this question. It can be difficult getting a feel of someone’s lifestyle when you’re online dating, so make sure to inquire about their daily routine! This will help you learn if you’d be compatible IRL. “What does a typical day look like for you?” “Tell me about your daily routine.” “What’s something you look forward to everyday?”

“How long was your longest relationship?”

Get to know a little about their past romances before meeting IRL. This type of question might come up on an in-person date, so why wait to ask? By asking now, before things get too serious, you can get an honest response without having to worry about your reaction. Plus, you can be honest in return without worrying about “ruining” anything. “What do you want in a relationship?” “How many partners have you had?” “Do you use dating apps often?”

“Do you have a bucket list?”

You can tell a lot about a person by their hopes and dreams. Chances are, they’ve put subtle hints in their dating profile about what they want in life, so play off of that! Keep them engaged in the conversation by asking them questions about them, all while giving you the chance to get to know them. Ask them about their biggest dreams and what's important to them! “What’s your wildest dream?” “I noticed you want to start a family someday. Tell me about that.” “If it was your last day on earth, what dream would you want to come true?”

“Would you rather…?”

Get a little flirtatious with this texting game. A game of “this or that” can be a great way to take a break from ordinary get-to-know-you questions while still learning something about them. All you have to do is message them two choices and see how they respond. Keep the choices relatively tame, or go for some spicier options to keep things interesting. “Would you rather eat bananas for the rest of your life, or eat apples for the rest of your life?” “Would you rather kiss someone you’ve never met, or make out with an ex?” “Would you rather go skinning dipping with a colleague, or go skinning dipping with a stranger?”

"Kiss, marry, or kill?"

Play this messaging game to learn more about how they make decisions. When given the chance to kiss, marry, or kill off three of their favorite celebrities, what would they do? This game will have you both laughing, and can give you a chance to learn why they make the choices they do. Simply message your online date the names of three famous people and give them the choice to kiss, marry, or kill them. “If you had to kiss, marry, or kill Jim Carrey, Adam Sandler, and Seth Rogan, what would you do?” “Kiss, marry, or kill Harry Potter, Professor Dumbledore, and Lord Voldemort.” “Taylor Swift, Selena Gomez, Billie Eilish…Kiss, Marry, Kill?”

"Never have I ever..."

Get to know their darkest secrets with this elementary school game. The game is simple: text them a statement starting with “Never have I ever” and wait to see if they have done the deed or not. If they have, give them a point and totally ask questions about it! Take turns asking “Never have I ever,” and the person with the most points at the end loses. Here are some statements to get you started: “Never have I ever cheated on a partner.” “Never have I ever read someone else’s text messages.” “Never have I ever sung in public.”

"What's your unpopular opinion?"

Give them a chance to tell you about themselves with this game. Even if you’ve asked them a million questions, chances are there’s still so much more to learn about them! To play this game, simply take turns sharing your most unpopular opinions. This is an excellent way to make your mouth drop and have a good laugh. “Unpopular opinion: I like pineapple on pizza.” “Friends isn’t funny. I know. Unpopular opinion.” “Onion rings are better than french fries. Prove me wrong.”