Kick a playful convo off with a quirky opener.
To really grab his attention, skip ordinary lines like “Hey.” A creative opener shows you want to give him the extra effort. If you’ve just met, cheerfully bring up how you ran into each other. Sending a playful message can help you start a convo with a guy who’s already your friend and jumpstart a connection that’s a little less platonic. "Hey, it’s Abby from the produce section. It was nice running into you at the grocery store! ???? Sorry about grabbing the last good plum. I’ll make it up to you.” "I saw that League of Legends was on your Steam wishlist. You still don’t own it after all these years?! I guess I’ll have to fix that.” "Accidentally bought an extra succulent. Do you have a green thumb? I need someone I like to hand this off to.”
Butter him up with compliments.
Give him tons of praise. Sending him admiring comments can be a quick way to break the ice. Compliment any special talents or personality traits of his that you’ve noticed. When you embrace him for who he is and how he acts, you also show him that you like him. "I really dig that you always speak your mind. You really don’t hold anything back!” "I saw you refill the water bowl of that dog during your break when its owners were inside the cafe. I love people who care about animals.” "I saw you at the show last night! Your bass riff was incredible!”
Be his go-to for gifs and memes.
Make him laugh on the regular. It will show you’ve been paying attention to his sense of humor. Try to learn about his favorite tone and subjects when it comes to jokes. If you find memes that match his taste in jokes or focus on topics he talks a lot about, he may feel even more special. "Sorry to hear work was so rough! Here’s a pic of sandpaper to show I feel your pain.” "Found this meme that made me think of you! ???? Total horror movie cliché, right?!” "Thought this motivational poster was right up your alley! ”
Chat about what you’re both looking forward to.
Swap calendars and talk about what you’re doing next weekend. Not only will you learn more about each other’s hobbies and interests, but you also open up the chance to share them together. For example, you can tell him about an event you’re going to. You can also express excitement about one of his activities, which might make him invite you along. Either way, you give him a hint that you’d like to spend more time around him. "Hey, I have an extra ticket to this concert tomorrow night. Want it?” "No way?! You found a hiking spot in this town? I’d love to see it.” "I’m new to this area and need a spotter at the gym. Would you be interested?”
Keep it chill and relaxed.
If you’re feeling more shy, casual texts keep it low-pressure. This allows you to buy more time and reveal your feelings when the time is right. Reach out when you have free time or answer his texts in an easygoing tone to let him know you’re interested without coming on too strong. Staying laidback also lets him know you can unwind around him. "TGIF. Super tired and just kicking back with some hot chocolate. What’re you getting into?” "Yeah, I’m down for a hike. I need to get some new shoes though, tbh. What brand do you think I should get?” "Just got back from a family reunion. Do I have some stories for you…”
Play hard to get.
You don’t always have to be available to prove you like him. Texting too much can sometimes feel more like a chore and less like a fun, cute game. Making him wait can also push him to try and pursue you. Put a pause on getting back to him right away—just don’t keep him guessing too long or he may think you’re not interested. Letting one or two days pass can be enough to keep your dynamic fresh. "Sorry, just saw this.” "Can I get back to you?”
Send open-ended texts to keep him on his toes.
Shoot him a quick text to show your playful, mysterious side. The right one-liner can highlight how laidback and fun-loving you are. A clever curveball can also shake up the energy. If you don’t sound too formal or serious, he might pick up that you want a light conversation. Sending a short message can also encourage him to chime in and be in on the game. "Guess what?” "The joke’s on you!” "Let’s skip the small talk.” "You know what I’m in the mood for?”
Ask deep questions to connect with him.
Steer the conversation somewhere less casual to make him open up. By picking his brain about matters that take time to think about, he might stay on the phone and open up. You can ask about his value system, life philosophies, family life, hopes, or even fears. Tell him you’ve been dying to learn more about him with a fun, flirty, deep question. "If you had all the money in the world, how would you spend it?” What do you think you’ll be doing in ten years?” "Do you think it’s better to be hopeful or realistic?”
Hit him with a flirty text.
Turning up the heat can spell out that you’re attracted to him. Start off slow by complimenting his outfit or haircut. Directly talk about his looks or how you’d like to be physically near him to drop more obvious hints and really spice things up. "Did anyone tell you that you have the best jawline?” "Okay, I don’t know if we can still be friends if you keep wearing that leather jacket! You’re kind of giving me bad boy vibes.” "Gotta love the winter season. I just want to jump into your arms when you wear that sweater.”
Invite him to a local spot to hint you want a date.
Asking to hang out lets him know you think he’s good company. If you’re usually around each other in a certain setting, suggest a new hangout spot. If you’re clear and specific about the logistics of your plans, it might let him know that spending time with him is a priority. Choosing a place where you both can have fun can help sparks fly. "I think we both need to let off some steam! Paintball on Saturday?” "You said you like Thai and I know the absolute perfect place. Are you free Thursday?” "I feel like I only see you in the morning. Why don’t we catch a movie tonight?”
Heap on the affection.
Cute and sincere messages are the hardest to miss. Sometimes, you don’t want to play it cool. If you want to show how warm he makes you feel, talk about how you’d like to cuddle up to him. You can also thank him for going the extra mile for you or say that he makes you feel super special. Try these sweet texts to give him a more obvious signal that you like him. "Thank you for listening to me today. I wish I could give you a hug right now.” "You’re cramming for finals? Can’t I come over and cook you a nice dinner? You deserve it.” "No one else can make me feel as giddy as you do.”
Point out signs that he likes you.
Encourage him to admit his feelings first. If he confesses his feelings for you, then you might not need to drop a lot of hints. Casually asking why he’s been awkward around you or why he wants to spend time with you could lead to him explaining that he has a crush on you. That way, you can reveal you have one on him, too. "Hey, thanks for coming to my open mic for the third time in a row. Is there something you’re trying to tell me?” "Wow, have we really been texting every day? Do you talk with all your friends this much?” "You ‘love’ react to all my jokes! Am I really that funny?”
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