Method 1 of 10: Say hello in a super friendly way.
- “Hey! This is Jason from algebra class. How are you?”
- If you know them in real life, feel free to be a bit more personal. You could try, “Hi Suzie! What have you been up to? We haven’t talked in a while!”
- For a flirtier intro, say something like, “Hey there stranger! What’s going on?”
Method 2 of 10: Ask a few open-ended questions.
- “What’s the most exciting thing you did today?”
- If you got to school together, you might ask, “How are you enjoying Ms. David’s English class? Do you like the book we’re reading?”
- For a flirtier approach, you could ask, “What’s your favorite quality in a boyfriend/girlfriend?”
Method 3 of 10: Spark a fun convo with a “Would you rather?”
- “Would you rather be able to see 10 minutes into the future, or go back 10 minutes into the past?”
- “Would you rather be able to fly, or turn invisible?”
- For a flirtier option, you might ask “Would you rather spend a romantic vacation snowed in at a cabin, or laid out on a private beach?”
Method 4 of 10: Send a funny or flirty meme or gif.
- You could always add something like, “This reminded me of you!” if you really want to add some flirty context or make them feel like you’re trying to get closer to them.
Method 5 of 10: Ask for a suggestion.
- “Have you seen anything good on Netflix recently? I need a new TV show to binge.”
- “Read any good books lately? I enjoy reading, but nothing has piqued my interest lately. You seem like you’re well-read!”
- “Do you have any tips for dealing with Mr. Spitz’s biology class? I know you’re good at science, but I just can’t seem to pass any of his tests.”
Method 6 of 10: See if they’ll help you with something.
- If they’re into video games, you might ask, “Hey, I can’t beat this boss in this new game I got. Can you help me out?”
- If the person is really good at a school subject, you could ask, “Is there any way we could study for this next history exam? I really need to pass this one to get my grades up!”
- For something fun, you might ask, “Hey, you’re stylish. Any way you’d be interested in helping me do some shopping? I’ve got to update my wardrobe.”
Method 7 of 10: Compliment them.
- If you go to school or work together, you might say, “Hey, I really liked your outfit today. That’s a cool shirt!”
- If you don’t know them super well, drop a compliment while you two are talking. Even something as little as, “That’s a really clever way of thinking about it!” can make someone’s day.
Method 8 of 10: Lean into whatever makes them open up.
If something sparks a big response, guide the conversation to focus on that. Shy people occasionally play it close to the vest when it comes to their interests or beliefs. If they open up a bit on something or they seem particularly interested in a certain subject, focus on that. Ask follow-up questions, share your opinion on the subject, and bring it back up in the future!
- For example, if you sent a gif of a smiling gorilla acting silly and they say, “I used to love going to the zoo as a kid,” talk about that! Ask them which animals they like, or talk about your favorite exhibits at the zoo.
- If you ask them about what they’re doing and they say they’re playing a video game, you might ask, “Oh, fun! What game is it?” After they tell you, ask, “Is it fun?” or, “Would I like it?” The more you can get them talking about something they enjoy, the more open they’ll be with you.
Method 9 of 10: Carry your text conversations over into real life.
If you want to connect more with this person, reference your texts IRL. If the two of you had a great conversation over text about a sports team, bring it up the next time you see them. The more you can carry your text message momentum over to real life, the easier it will be for them to build a relationship with you. Shy people often lock up in real-life interactions, which is why they prefer texting so much. By carrying that text conversation over into real life, it will be easier for them to relax.
- If the two of you were laughing over text messages, turn it into an inside joke the next time you see them.
- You might just bring something up to remind them of your chats. You could say something like, “What was that movie you told me about last night? I keep forgetting to write it down!”
Method 10 of 10: Don’t get frustrated.
It can feel like you’re carrying the conversation with a shy person. After a while, that can get kind of irritating. The good news is that once you’ve established a rapport with this person, things will get much easier. In the meantime, stay positive, be empathetic, and don’t be super self-conscious that you’re doing a lot of the talking.
- Don’t read too much into it if they aren’t super talkative. It may feel like they have no interest in hanging out or talking, but it’s much more likely that they’re just a little nervous about opening up. Give it time!