This article was written by Julianne Cantarella and by wikiHow staff writer, Hunter Rising. Julianne Cantarella is a Dating Coach, Certified Life Coach, Licensed Social Worker, and the CEO and President of New Jersey's Matchmaker. With over a decade of experience, she specializes in helping women heal from a heartbreak and create healthy long-term relationships. Julianne created a comprehensive transformational date coaching program From First Date to Soulmate™ that has helped hundreds of women find love. She holds a Bachelor of Social Work (BSW) from Ramapo College of New Jersey and a Master of Social Work (MSW) from Fordham University. Julianne has contributed to numerous media such as Your Tango Online Magazine, 24Seven Wellness Magazine, and Talk of The Town Magazine. She has also been featured as a relationship expert on CBS, iHeartRadio, and PBS “This Emotional Life Project.”
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If you just got a text from the guy you’re chatting with, the ball is in your court to make the next move. We know that you want to show off how fun and exciting it is to talk to you whether you’re flirting or keeping it casual. Luckily, it’s super easy to continue the conversation no matter what he says. Keep reading for a ton of tips and example responses you can copy and paste so he stays interested!
This article is based off an interview with our professional dating coach and licensed social worker, Julianne Cantarella. Check out the full interview here.
Steps
Ask him about his day.
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See what he’s up to for an easy icebreaker. If you just want to have a casual conversation and he doesn’t give you a lot to work with, just ask your guy how he’s doing. See if he has any plans, ask him how his day has gone so far, and check if he has any exciting news. From there, you can go on to talk about almost anything and keep the conversation going.
- For example, you could say something like, “Hey 🙂 how are you doing today?”
- If he asks you what you’re up to, you might say, “I’m just chilling at home tonight. Do you have any big plans?”
Send back a sassy and silly response.
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Show off your sense of humor to keep your conversation light-hearted. Guys will love when you text them back with something witty since it shows that you aren’t too serious. Keep your message short and sweet, and include an emoji or laugh at the end of the message so he knows that you’re joking around.[1] X Expert Source Imad Jbara
Dating Coach Expert Interview. 22 September 2021.- For example, if he says something like, “Did you have a good day” you may say, “Absolutely not!” followed by, “I had a GREAT day haha.”
- When he says, “What are you doing today?” you could be flirty and reply, “Why, do you want to go out or something? 😏” or keep it casual by saying, “Well I was relaxing until you massaged me 😂”
- If he texts you, “I wish I could see you,” you could say something like, “Then go check out my Instagram 😉”
Give a flirty compliment if you’re into him.
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Guys love hearing what you like about them. If a guy flirts with you and you’re crushing on him, don’t be afraid to say something sweet and genuine back. Mention something that you love about his personality or how he looks to let him know you’re interested too. Just be careful not to come on too strong since it could make him feel a bit uncomfortable.[2] X Expert Source Julianne Cantarella
Dating & Relationship Coach Expert Interview. 6 August 2021.- If he makes a joke, you could say something like, “LOL you’re the funniest person I’ve ever talked to!”
- When he sends a selfie, you might say, “Has anyone ever told you that you have the cutest smile? 🥰” or, “Wow, I love that outfit on you!”
- If he calls you cute, you could reply with, “But you’re ten times cuter than I’ll ever be!”
Let him know you’re not interested if you’re not feeling flirty.
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Be honest so he doesn’t get the wrong idea. Setting boundaries is an important part of any friendship or relationship. Even if you like the guy, it’s okay if you aren’t in the mood to flirt during your conversation. Let him know that you want to keep it casual and that you’re not ready for that sort of conversation so you don’t feel uncomfortable chatting with him.[3] X Expert Source Julianne Cantarella
Dating & Relationship Coach Expert Interview. 6 August 2021.- If he comes on a little too strong, soften the blow with an emoji. You could say, “We should probably get to know each other better before we start talking about that. Tell me more about yourself 🙂”
- If you aren’t interested in a relationship at all, you might reply, “You’re really nice, but I just want to stay friends.”
- If you’re really uncomfortable, be honest and say something like, “I’m not really comfortable talking like this. Do you mind if we change the subject?”
Ask him some open-ended questions.
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Open-ended questions make him type out longer responses. Start your questions with “why,” “what,” or “how” since he won’t be able to answer with a one-word response. When he brings up an interesting topic, dig a little deeper and ask him to tell you more about it. That way, you can build a better friendship or see if you’re a good match for each other.[4] X Research source
- If he mentions that he has work later that day, you might ask “Oh nice! What do you do?”
- When he says that he’s really into a band, you could ask, “I haven’t heard of them! What’s your favorite song?”
- If he brings up his favorite hobby, try saying, “That’s so cool, how did you get into that?”
Tease him to keep him on his toes.
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Poke a little fun at the guy so your convo doesn’t get too serious. Texting a guy should be fun whether you’re just friends or looking for something more romantic. Since sarcasm or jokes might be a little tough to read over text, laugh or add an emoji to your message so he doesn’t take it the wrong way. If you’re into the guy, teasing can be a great way to turn him on too![5] X Expert Source Imad Jbara
Dating Coach Expert Interview. 22 September 2021.- For example, if he accidentally makes a typo, you could say, “Well I’m glad you had so much ‘fum’ last night haha.”
- If he’s bragging about being good at sports, you might try saying, “Is that a challenge? Because I bet I could beat you!”
- If he mentions that he wants to get together, you could get flirty and reply, “I bet we’d have a lot of fun together 😉.”
Share a pic of what you’re doing.
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You build a better connection when you show him a glimpse of your life. If there’s not a lot to work with in his message, snap a quick picture or video of whatever you’re doing to show him what he’s missing. Just be cautious sending any explicit pictures, even if you’re into him, since they might make him uncomfortable or get shared around.[6] X Research source
- For example, if he asks what you’re up to, show him the activity you’re doing and say something like, “Have you ever tried this?”
- If he mentions that he wants to hang out, you could send a selfie of you on a couch saying, “There’s a spot right here for you!”
End on a cliffhanger to build up anticipation.
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The guy will have to respond again if he wants to learn more. Rather than telling the guy everything about yourself right away, keep things a little mysterious at first. Briefly mention what you want to talk about, but leave out all of the juicy details to make him even more curious. He’ll definitely ask you more about it if he’s still interested in the conversation.[7] X Expert Source Imad Jbara
Dating Coach Expert Interview. 22 September 2021.- If he mentions a memory from his childhood, you might say “OMG I’ve done something like that too! It’s kind of a funny story.”
- If he mentions his favorite musician, you could say, “Oh I saw them in concert! You wouldn’t believe what happened during the show!”
- If he says he wants to hang out, turn up the heat by saying something like, “I have an idea of what we could do when we’re together 😉.”
Keep it lighthearted with emojis.
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Emojis clearly set the tone of your conversation to avoid confusion. When you talk to a guy in person, it’s easier for him to judge how you’re feeling from your voice and body language. Over text, it’s a bit tougher for him to know how you’re feeling, so find an emoji that matches your mood and put it somewhere in your message.
- If you want to keep it casual, try using 🙂, 😋, or 😀.
- When he says something funny, send 😂, 🤣, or 😆.
- If you want to get a little flirty, include 😉, 😘, or 😏.
Make plans to get together if you want to know him more.
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Bonding in person lets you check if you have good chemistry. Texting is a great way to stay in touch, but it’s not the best way to chat if you want to build a relationship. If you want to be better friends or test the waters to see if he’s someone you like romantically, suggest seeing each other to chat instead. If you aren’t able to meet up in person, you can always recommend a phone call or video chat so you can still hear each other’s voices.
- If you want to have a casual hangout, you might say, “We should def hang out! How’s this Friday?”
- If he mentions that he likes you, you could say something like, “Why don’t we go out to dinner this weekend then? 😊”
Use exclamation points to show your excitement.
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A guy’s more likely to keep talking if you seem eager to chat. When you send a message with a period, he might think you’re angry or being short with him. Let him know that you really enjoy texting him by ending a few sentences with exclamation points, but be careful not to double-up on punctuation or use too many since it could seem insincere.[8] X Research source
- For example, when he starts a conversation, you can eagerly say, “Oh hey! So glad to hear from you! What’s up?”
- If he talks about one of his hobbies and you’re into it too, you might say, “OMG that’s so cool! I’m a huge fan too!”
Have a purpose when you’re texting.
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Work towards a goal so you don’t have pointless conversations. Even though texting is an easy way to stay in touch, your messages might get stale if you aren’t having a real conversation. Make sure each text you send is working towards something, like getting to know him better or setting up a time where you can get together in person. That way, you’re not interrupting one another just to stay in touch.
- Keep your texting convos positive and lighthearted so you have fun messaging back and forth. If you have to discuss a more serious topic, try to do it face-to-face instead.
Be wary responding to one-word texts.
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Short responses are usually a sign he doesn’t care or put in a lot of effort. If a guy really cares about building a relationship, he’ll take his time to type out a longer message. When he texts you “hey” or “WYD,” he’s probably not interested in building a deep bond with you and might only want a hookup. If you still want to keep his attention and continue the conversation, try sending back longer messages to encourage him to talk more.
- For example, you might reply, “Hey! So good to hear from you! How have you been lately?”
- If you keep getting one-word responses, leave his messages unanswered and save your energy for people that want to build something more with you.[9]
X
Expert Source
Julianne Cantarella
Dating & Relationship Coach Expert Interview. 6 August 2021.
Wait until he replies before texting again.
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Double-texting might make you seem desperate. Once you send your reply, resist the urge to check up on him again if he doesn’t respond right away. There’s a chance that he might be busy with something and he’ll reply back when he has the time. When he finally does respond to you, try to wait the same amount of time between messages so it doesn’t seem like you’re always available or waiting around for him.
- If he doesn’t respond after 2 or 3 days or if he ghosts you completely, he probably wasn't interested in chatting with you to begin with. Move on. He's not worth your time and you deserve better![10] X Research source
Expert Q&A
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QuestionHow can I keep a guy interested over text? I'm worried he's bored by me.Imad JbaraImad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
Dating CoachStay a little illogical and fun. You don't always have to reply with super reasonable or "normal" texts. Throw in a joke, insight, or little unrelated quip. That keeps the conversation from getting stale and boring. -
QuestionHow can I compliment a guy over text without it being weird?Imad JbaraImad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
Dating CoachI really like complimenting guys for their traits. I think it plays to their masculinity and sense of self. So saying something like, "I really like how you take initiative," or, "I really appreciate how kind you are," is really effective in my opinion.
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References
- ↑ Imad Jbara. Dating Coach. Expert Interview. 22 September 2021.
- ↑ Julianne Cantarella. Dating & Relationship Coach. Expert Interview. 6 August 2021.
- ↑ Julianne Cantarella. Dating & Relationship Coach. Expert Interview. 6 August 2021.
- ↑ https://www.regain.us/advice/how-to/how-to-keep-a-conversation-going-with-a-boy-to-get-to-know-him-better/
- ↑ Imad Jbara. Dating Coach. Expert Interview. 22 September 2021.
- ↑ https://www.regain.us/advice/chat/guy-texting-advice-9-ways-to-keep-him-engaged-in-conversation/
- ↑ Imad Jbara. Dating Coach. Expert Interview. 22 September 2021.
- ↑ https://youtu.be/9UgZS2fA8MQ?t=121
- ↑ Julianne Cantarella. Dating & Relationship Coach. Expert Interview. 6 August 2021.