Ask him about his day.
Find out what he’s up to so you can catch up every day. Keep it casual by asking how he’s doing if you’re not sure what else you should talk about. Ask if he has plans for the day or if he had anything exciting happen to him recently. Once he replies, keep digging for more details to carry on the rest of the conversation. For example, you might text, “Hey! How’s your day been going so far?” or “What’s the most exciting thing that happened today?” Even if he doesn’t ask you, respond with what you’re up to as well since he might want to ask you more about it.
Pose a few fun, open-ended questions.
Your guy is more likely to respond to questions. Open-ended questions usually start with words like “what,” “how,” or “why” so he can’t just reply with one word. Learn more about the things he likes to do, ask him for a recommendation, or try out a silly icebreaker so you can get the conversation going. Once he answers, ask some follow-up questions so you can keep chatting. You could ask him, “What do you like to do in your free time?” If you want to get his advice, try something like, “What movie do you think I should watch tonight?” or, “What games do you think I’d like to play?” Fun icebreakers include, “What 3 things would you bring to a desert island?” or “What would you do if you had a million dollars?”
Bring up your common interests.
He’ll love gushing about his favorite things. If you’re already friends on social media, look through his profile to find a few things that he likes to do. Casually mention what you find in one of your messages and let him know that you’re into it too! Ask him more to talk about it more so you can dig deeper and build up your connection. If he’s really into football, you could say something like, “The Ravens are my favorite team too! Who’s your favorite player?” or “OMG I love football! What did you think of the game last night?” If he’s into art, you might say, “That’s so cool you’re into painting! Is there an artist that you really look up to?” or “I wish I knew more about art. Are there any museums you think I should check out?”
Flatter him with a compliment.
Hearing nice things might encourage him to reply. If you’re feeling flirty, mention something that you really appreciate about the guy you’re chatting with. You could talk about his looks, personality, or anything else you admire about him. He’ll either thank you, or he may compliment you back if he’s interested in you too! Just be careful not to come on too strong if you started talking recently since it may make him a little uncomfortable. Say something like, “I saw your Insta pic! You’re so handsome in a suit! ????” or “I love seeing your smile!” You might say, “You always know just how to make me feel so special,” or, “You have such a way with words, you could be a poet!”
Be a little mysterious.
Keep a few details hidden so he has to ask for more. Rather than telling the guy everything right away, end your message on an intriguing cliffhanger. He’ll be so curious about what you’re up to, he’ll reach out again to ask you for more. Give him a little more to work with in each reply so you can keep texting back and forth. Message him something like, “You would not believe what happened at work today…” or, “That reminds me of a funny story from when I was younger! You’re going to laugh so hard at this.” If you want to be a little flirty, you might try, “I had a crazy dream about you ????.”
Send him a few pics.
Show him what you’re up to so he has a small view of your life. Your guy will love seeing you having a good time, so snap a pic or record a video to give him a quick glimpse of what you’re doing. Ask him a question or add a fun, flirty caption to show him that he’s really missing out. You could send him a selfie and say, “Just got a new outfit! What do you think?” You could send him a picture of where you are and say, “This would be so much fun if you were here! Wish you could come too!” Avoid sending any explicit pictures since they might make him feel a bit uncomfortable.
Make plans to meet up in person.
You’ll build a better connection when you’re face-to-face. Even though texting is a great way to stay in touch, ask if he wants to meet up and do something together if you want a deeper relationship. Suggest a fun date or a casual hangout so you can get to know each other better and test out your physical chemistry. If you live far away or can’t easily get together, you can always try talking on the phone or hopping on a video call. You might ask, “OMG my favorite band is playing here this weekend! Do you want to come with me?” You could say, “Do you want to grab a coffee and chat sometime soon?” or “Are you free for dinner on Friday? I’d love to see you ????.”
Have a reason for texting him.
Messaging him without a purpose might lead to dead-end conversations. Conversations can get pretty stale if you’re just texting without any reason. Whenever you send a text, work towards getting to know him better or planning a date. That way, you aren’t interrupting what he’s doing or making him bored.
Keep your messages lighthearted.
Focus on having fun while you’re texting to keep him hooked. Texting isn’t a great way to have serious conversations since the guy may misread the tone of the message. Stick to fun topics and learning more about him with every message. If you ever need to have a deeper discussion, save it for chatting on the phone or when you meet up face-to-face. Reader Poll: We asked 328 wikiHow readers about the best ways to build a connection with someone they like over text, and only 7% of people recommended bringing up super deep, philosophical topics. [Take Poll] Instead, keep it light, fun, friendly, and sweet—save the serious topics for in-person conversation!
Let him reach out first a few times.
Keep him waiting to show him you have a life. If you’re always texting a guy, he might think that you’re always available. Rather than always being the first one to message him, put your phone away and wait for him to text you first. If he’s really interested and wants to continue the conversation, he’ll eventually reach out to talk to you. When he messages you, you can sometimes tell him that you’re busy to keep him on his toes. You might say, “Hey! So good to hear from you but I’m with friends right now. I can talk later though ????.”
Wait until he responds to message him again.
Give your guy time to reply so you aren’t double-texting him. If your guy opens up his messages and sees a wall of text, he might not know what to respond to. If he doesn’t reply right away, he might just be busy or doing something else. Once he finally does respond, give it the same amount of time before you reply to him so it doesn’t seem like you were waiting by your phone. If he only sends one-word responses or takes a few days in between replies, it may be a sign that he’s not interested. Move on and put your energy into someone else who wants to build a deeper connection with you.
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