How to Text a Shy Person

Say hello in a super friendly way.

If you don’t know them very well, start small with an upbeat greeting. Unless you already have an established relationship where you know one another fairly well, start slow with a basic greeting. If this is the first time you’ve chatted, explain who you are as well. Be kind and pleasant to disarm any fears they might have. Throw out a simple follow-up question to give them something to respond to. You might try: “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?” Keep in mind, this works best if you already know them so it comes off as a little ironic and friendly.

Ask a few open-ended questions.

To connect on a deeper level, ask them about themselves. Shy people will rarely volunteer information about themselves out of nowhere, but connecting over personal info is one of the best ways to bond with someone. Try asking some low-stakes but slightly-personal questions to get them to open up. You can either throw these out randomly as you text on and off over time, or ask questions organically as the conversation develops. You might try: “What’s the most exciting thing you did today?” If you go 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?”

Spark a fun convo with a “Would you rather?”

To keep a casual conversation going, try a playful “Would you rather?” If your conversation ever feels like it’s losing momentum or you aren’t sure how to breach a wall of one-word answers, pick a playful party game “would you rather” question and ask them to answer. If they only give you another one-word answer, follow up with, “Why?” If they’re interested in chatting, they’ll give you something to respond to. You could ask: “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?”

Send a funny or flirty meme or gif.

Nobody said you need to write anything to keep a text convo going! If you want to spark an interaction out of nowhere or the chat turns a little cold, get visual. The more you two text back and forth, the easier it will be to build a relationship in the future. If it’s hard to connect using language right now, pick a fun or captivating meme or gif and just send it their way. This is a good idea if you already have a sense for their kind of humor. If you have no idea what they find funny, try testing the waters with something uncontroversial. If you know they love physical humor, send them a gif of someone falling over. If they prefer more random humor, send them a strange and goofy meme. 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. Expert Answer Q How do I ask a shy girl out over text? Elvina Lui, MFT Elvina Lui, MFT Marriage & Family Therapist Elvina Lui is a Licensed Marriage and Family Therapist specializing in relationship counseling based in the San Francisco Bay Area. Elvina received her Masters in Counseling from Western Seminary in 2007 and trained under the Asian Family Institute in San Francisco and the New Life Community Services in Santa Cruz. She has over 13 years of counseling experience and is trained in the harm reduction model. Elvina Lui, MFT EXPERT ADVICE Answer from Elvina Lui, MFT: Invite her out on a low-stakes outing, like a trip to a coffeeshop. If that goes well, progress to something more official, like a movie or dinner date.

Ask for a suggestion.

This is a great way to find an “excuse” to text a shy person. Not only is this a good reason to text someone out of nowhere, but it’s also a good way to get to know one another. By asking for a suggestion, they’ll share something they enjoy or find interesting. This will give you something to ask follow up questions about, and the two of you might develop a deeper conversation as a result. You might ask: “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.”

See if they'll help you with something.

To move from chatting to something more involved, ask for a favor. This is a really good option if you’re looking to build a romantic relationship or friendship. By asking for help, you’ll create an excuse for the two of you to do something together. Engaging in an activity together will give you a space to get to know one another better and create a foundation for future conversations. 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.”

Compliment them.

Shy people are occasionally insecure, and a compliment may put them at ease. Everyone likes to feel good about themselves, but this is especially important with shy people. When you’re shy, you often over-analyze things and get self-conscious. Hearing a compliment can deflate a lot of that anxiety and fear they may have. This is a great way to really build a relationship, whether it’s platonic or romantic. 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.

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.

Continue your conversation IRL.

Use the topics from your text convos to connect more in person. If the two of you had a great conversation over text about a sports team, bring tonight’s big game up the next time you see them. This makes it much easier for them to open up around you. Shy people often lock up in IRL interactions, which is why they prefer texting so much. By bringing the texture of that 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. For example, if you were laughing over a bad sweater one of your teachers wore and another student shows up next week dressed in something goofy, you might whisper, “James is really looking like a regular Mr. Davis today.” You might just bring something up to remind them of your chats. You could say something like, “I wanted to watch that movie you told me about last week but I couldn’t find it online. Do you know if it’s on Netflix or something?”

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! If it feels like they never reach out first even after a few conversations and they don’t try to hang out in person whenever you see them, it’s possible that they just don’t want to hang out with you. It should be pretty obvious after those first few text chats.