Dating Tips for Chatting Online: How to Start a Great Conversation and Keep It Going

Co-authored by Lisa Shield and Hannah Madden

Last Updated: November 30, 2022 References

When you first enter the dating pool, online dating can seem like a pretty intimidating beast: how do you know what to talk about? How quickly should you reply? And how long do you need to chat online before taking things to the next level? If you feel like a fish out of water, don’t worry—you’re not alone! We’ve compiled some of the most helpful tips for chatting online so you can get to know your potential date before asking them out.

1

Talk about a common interest in your opening message.

Check out their profile to see what they like to do. Once you learn a little more about them, you can craft a message that talks about something you two have in common. Maybe you graduated from the same college, or maybe you both participate in the same hobby. It doesn’t even have to be anything specific — if you both like being outdoors, that’s great, too! Try something like:^{[1]
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- “Hey! I saw your hiking pics, they look so pretty. I love hiking, too!”
- “I’ve never met another person who does roller derby! How often do you hit the rink?”

2

Ask them questions about themselves.

Online dating is all about getting to know the other person. Since the only things you know about them are from their profile, try expanding on those to get a little more insight into who they are. You don’t have to treat it like an interrogation (since that can feel a little intense), but some casual questions near the beginning of your convo can really get the ball rolling, especially if they have some pets or traveling pictures in their profile. Try things like:^{[2]
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- “That pic of your pup is so cute! How old are they?”
- “Have you ever been to the rose garden?”

3

See if they like living in the area.

This is an easy way to start a fun conversation. If you two live nearby (and most dating sites will connect you with people around you), see how they like the place you’re in. You could also ask them how long they’ve been here or if they plan on staying a while, just for a few fun things to talk about. Try something like:^{[3]
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- “How long have you been in San Francisco?”
- “Do you like living here in Minnesota?”
- “What’s your favorite thing about living here?”

4

Chat about pop culture.

There’s always a new TV show or movie to talk about. See if they caught the newest binge-worthy Netflix special, or ask them if they plan on seeing the next big box office in theaters. Plus, if they haven’t seen one of your favorite things yet, this is a great way to segue into a date! Try something like:^{[4]
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- “You’ve got to watch that new Netflix documentary about mushrooms. It’s insane!”
- “Are you gonna go see the new Batman movie? I’m pretty curious about it, honestly.”

5

Give them a few compliments.

You can flatter your potential date by telling them something you like. Since you don’t know this person well yet, stay away from anything physical, and compliment them on something you noticed in their profile. Stick to 1 or 2 compliments per conversation, just so it doesn’t go overboard. You could say something like:^{[5]
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- “You have such a nice smile! It really shines through in all your pics.”
- “You look like you have such a good fashion sense. I love your outfit in that first pic!”
- “You have such a good sense of humor. I can tell you’d be fun to hang out with.”

6

Send a few flirtatious messages.

You can send a few cheeky messages if you get that kind of vibe. Some people appreciate a little harmless banter, especially if you’ve had a fun conversation so far. Try a little bit of teasing (in a flirty way!) to let your potential date know that you’re interested. You might say something like:^{[6]
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- “Red Sox fan, huh? You must be pretty bummed out this season!”
- “You’ve never seen Twilight?! Wow, idk if this will work out.😉”

7

Throw out a few hypotheticals.

These fun, fake scenarios can get a goofy conversation flowing. Come up with a “Would you rather” or “What would you do if…” question that your potential date can answer. If you disagree, don’t be afraid to hold a (non-serious) debate! Try something like:^{[7]
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- “What would you do if a zombie apocalypse started right now?”
- “Would you rather fight 10 duck-sized horses or 1 horse-sized duck?”

8

Try to reply quickly.

Conversations tend to fizzle out if you leave them for too long. Try to check your online dating account at least once a day, or even more if you’re actively having a conversation with someone. If you can’t keep up with their messages, consider giving out your phone number instead (if you feel comfortable with that).^{[8]
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- If you do decide to give out your digits, say something like, “I’m not on this app a ton. Here’s my number if you want to keep chatting.”
Expert Answer

Q

How do you make a conversation less boring on Tinder?

Kristina Mirgorodskaya
Dating Expert
Kristina Mirgorodskaya is a Dating Coach and the Marketing Director of Amiccio, a New York City social app that helps singles make new connections. Amiccio connects singles by hosting parties, socials, beginners salsa, bachata, and tango classes, and speed dating events. With over four years of experience, Kristina specializes in leveraging people skills, cultivating welcoming environments, and intercultural communication. Her expertise allows her to easily bring people together. Kristina earned a degree in business from Baruch College.

EXPERT ADVICE

Answer from Kristina Mirgorodskaya:

Try to be creative with your questions and responses! You can comment on specific things, like their profile descriptions or image. Just try to keep it at 5-6 exchanges before suggesting to meet—longer, drawn-out conversations tend to lose momentum, especially when you are busy with other parts of life.

9

See if they want to meet IRL.

The goal of talking to someone online is to meet up in-person. After you’ve chatted back and forth for five to six times, suggest meeting up somewhere casual, like a cafe or a bar. If they agree, you can set a time and a place to have a fun IRL date with someone you met online.^{[9]
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- Say something like, “I’ve really enjoyed our convo so far. Are you free this weekend to grab coffee or a drink?”
- Sometimes, people are a little wary about meeting up in-person too soon. If the person you’re chatting with wants to talk online a little more before meeting up, don’t be offended! They’re probably just trying to be safe.

10

Try a video date to take things slow.

If you don’t want to meet IRL yet, try this instead. A lot of dating apps have a video chat feature, but you can also use FaceTime or Zoom to talk to your date on a computer or your phone. This can be a nice way to take things slow and keep yourself safe if you’re wary about meeting a stranger in-person.^{[10]
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- You could suggest it by saying something like, “I really like chatting with you! Do you have time for a video call this evening? I’d love to hear your voice.”

11

Don’t give out any personal info.

Keep your safety in mind as you chat with people online. Never give out your address or any personal information, like where you work. If you’re ever wary about someone you’re talking to online, try looking them up on social media to make sure they’re real. It’s okay to give people the benefit of the doubt, but online safety is just as important as real life safety!^{[11]
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- If anyone ever sends you creepy messages, feel free to block and report their profile.
- Try to be reasonably sure that they are real and not a scammer. Make sure that the person is following a nice conversation and not asking you about your money.

Expert Q&A

Question

What should I write in my dating profile?

Lisa Shield
Dating Coach
Lisa Shield is a love and relationship expert based in Los Angeles. She has a Master's degree in Spiritual Psychology and is a certified life and relationship coach with over 17 years of experience. Lisa has been featured in The Huffington Post, Buzzfeed, LA Times, and Cosmopolitan.

Lisa Shield

Dating Coach

Expert Answer

You should list your basic information and some adjectives that truly represent yourself. Remember, though, that men and women think differently, and there are things that you might say that are inadvertently a blatant turnoff to the opposite sex. My greatest tip then is to have someone from the opposite sex read your profile to give you some insights so you can filter information.