Whether you consider yourself a “bad” texter, or you have texting anxiety, or you struggle to break the ice with a guy, no matter. Regardless of who you’re pursuing, there are myriad ways to make yourself just as alluring over text as you are in real life.
Moreover, there are also bound to be inevitable situations you’ll run into over text during a courtship, like initiating plans, trying to get to know him better, or flirting. Below, I’ve compiled a list of examples that’ll allow you to take on each conversation confidently. You learn what to say to a guy over text in various scenarios.
What to say to him over text for the first time
Let’s say you recently exchanged numbers with a guy. The first impression is out of the way and it’s time to set the wheels in motion. So, what do you say to a guy you like? Find out below.
You: Hiya, how’s your day going?
WHY IT WORKS: Well, you gotta start somewhere, right? This is typically a promising (and neutral) place to start. Plus, he probably doesn’t have too many inquiries about how he’s doing or how his day is going, so he’ll appreciate that you asked.
You: Hey, it was great to meet you earlier/yesterday. [Recall a funny/interesting thing that happened.]
WHY IT WORKS: You’ll want to emphasize that you did, indeed, enjoy meeting him. Then, if you recall what happened when you met, it’ll show him that he left you with a great first impression.
You: Hope I run into you again soon!
WHY IT WORKS: This is ideal if you met him in real life the first time. Moreover, it’s simple, cute, and conveys interest.
You: Now that I know we both like [mutual interest], maybe we could try [place for mutual interest] 😊
WHY IT WORKS: Finding common ground from the jump gives you both a good reason to make plans and see where things go.
You: Did you hear about [event in your area] this weekend? I’ll be there for a bit—you should drop by 😌
WHY IT WORKS: You’re not rushing into an intimate setting just yet, so the pressure is off to go all out as you might for a first date. This passive sort of invite will set a casual tone, and if he can’t make it, you can at least discuss how the said event went afterwards.
What to say to a good-looking guy over text
While flattery is part of any courtship, you won’t want to come on too strong or resort to generic compliments. Get creative.
You: (Color, item of clothing, etc.) looks sooo good on you
WHY IT WORKS: Compliments are best when they’re specific, sincere, and thoughtful. Do you know how often men hear flattery of this nature? Probably not as often as they’d like to. Remarks like this are sure to elicit appreciation.
You: Your [specific feature] was/were the first thing I noticed about you
WHY IT WORKS: Once again, be specific with your flattery. If you were to just say “you’re so hot!” it wouldn’t hold as much weight as to highlight a specific trait.
You: Your passion for [something he loves] is super inspiring
WHY IT WORKS: Chances are, if a guy is handsome, he knows he is. So, why not focus on a non-physical attribute? It’ll convey that you care about not just his beauty, but his character and interests, too.
You: I have to ask—what cologne were you wearing when I saw you? It smelled so good, lol
WHY IT WORKS: Men who wear fragrances want to be noticed for it. When the intentional effort to smell good is recognized, they’ll relish in your acknowledgement.
You: You have great [arms, legs, hair, pecs, etc.]—what’s your secret 👀
WHY IT WORKS: Not only will he be flattered, but you’ll also get him talking about how he maintains certain aspects of himself. Much to be learned, here.
What to say to a guy over text to keep the conversation going
It’s normal to experience lulls in communication from time to time. But reigniting conversations is simple.
You: Whoa, did you see [thing that he would be interested in]?
WHY IT WORKS: Maybe it’s news about his favourite sports team, a funny tweet, or something you have a mutual interest in. Nonetheless, this approach is a great way to get him excited and encourage him to discuss something he likes.
You: Saw this, thought of you [insert screenshot or link of something he would be interested in]
WHY IT WORKS: A similar iteration of the former suggestion, this is a sweet way to show that you listen intently when it comes to his interests.
You: So, what are you up to this evening, [playful, tease-y nickname]?
WHY IT WORKS: My favorite way to establish playful banter is by teasing one another (but not going too below the belt). Maybe you can call him “coach” if he’s a fantasy football fanatic, or “giggles” if he has a distinct laugh. (Just remember, you need to be able to take what you’re dishing out.)
You: Send me your favorite playlist, please 😊
WHY IT WORKS: Music is a very dense topic to break the ice. Additionally, since most men don’t wear their hearts on their sleeves, their taste in tunes will shed light on what lyrically and sonically resonates with them.
You: What show are you currently binging?
WHY IT WORKS: Like music, the topic of television is bound to spark an in-depth conversation about content you love, hate, and everything in between.
What to text to a guy to make him want you
Time to turn up the flirtation in a way that’ll leave him wanting more and more of you.
You: If you’re interested in getting beat at [Nintendo, cards, Twister, etc.], that can be arranged 😌
WHY IT WORKS: A text like this is oozing confidence—even if you’re not good at any of those things. Even better? You can throw in a wager that’ll make the stakes higher (and hotter).
You: I’m looking for an excuse to wear [flattering garment of clothing]—let’s grab dinner this weekend
WHY IT WORKS: Dangle the carrot, girl! Frame this idea as a sort of privilege. You get a chance to step out in a sexy outfit, and he gets to be seen with you. Everybody wins.
You: You, me, and a bottle of red this Friday?
WHY IT WORKS: There are plenty of implications and undertones to a simple text like this. The biggest takeaway? Something intimate is probably going to happen, so I’d say it’s an irresistible offer for him.
You: Wanna play hooky and do [activity you’d both like]?
WHY IT WORKS: Spontaneity is sexy, and the rebellious feeling of ditching work together to do whatever will add some excitement to your courtship.
You: I’m leaving for vacation on Friday, but would love to hang before I take off
WHY IT WORKS: This will spark a sense of unspoken urgency for him to prioritize seeing you before you run off for an extended period. (Also, it’ll leave you both with the craving to revisit where you left off upon your return.)
What to talk about with a guy over text when you are bored
It could be a slow day at work, or you might be waiting in a serpentine line for restaurant reservations. If you’re going to text him to keep yourself busy, you’ll need some not-so-boring openers.
You: What are you getting into this weekend
WHY IT WORKS: This will toe the line of potentially making plans but also getting a glimpse into what he does in his spare time.
You: Tell me more about [something he’s good at or passionate about]—how’d you get involved in that?
WHY IT WORKS: A great way to make the dialogue interesting? Ask him thoughtful questions about his passions, hobbies, etc.
You: What’s the worst job you’ve ever had?
WHY IT WORKS: We can all commiserate about horrible jobs. This query is sure to open a hilarious, thrilling can of worms.
You: Down for a little friendly competition? 😉
WHY IT WORKS: There are various games you can play together from afar, like Words with Friends, Trivia Crack, or Cup Pong. Low-stakes competition can further cultivate fun banter between you.
You: How would your [mom, dad, best friend, brother, sister, pet, etc.] describe you?
WHY IT WORKS: We can assume he’ll pass this unique question back to you, so this exchange will give a deeper sense of your relationships to your nearest and dearest.
What to say when a guy says he wants to cuddle over text
Approaching a new level of intimacy? Bring on the cutesy stuff.
You: Sounds like we should plan a movie night, eh?
WHY IT WORKS: So long as you’d like to bring this idea to fruition, you may as well pitch an idea to make it happen.
You: Big spoon or little spoon?
WHY IT WORKS: It might seem like a silly question, but it’s a valid one! This could also be a great way to find out what other forms of physical intimacy he likes to give and receive (i.e., forehead kisses, handholding, playing with your hair).
You: Prove it 👀
WHY IT WORKS: This will challenge him to get creative in how he wants to “prove” his desire to cuddle with you. (And… it might even result in something spicy, so proceed with caution!)
How to reply when he says he wants to kiss you over text
Things are heating up! He’s confessed he wants to lock lips. Lean into it, but don’t come off as too eager.
You: Oh, really? I was just thinking the same thing 😇
WHY IT WORKS: He made his move (albeit electronically), so reciprocate cheekily to add even more whimsy to the flirtatious exchange.
You: I dare you to 👀
WHY IT WORKS: A playful challenge met with forthrightness lets him know you’re ready to take that next step.
You: That can be arranged 😌
WHY IT WORKS: It’s. Going. DOWN! Now, let him spearhead when and where.
What to say to a guy over text to get to know him
If you want to know your suitor beyond the surface, it’s important to have some thought-provoking questions prepared—but remember to take it slowly. Prodding with too-personal inquiries early on could backfire.
You: I’m looking for something to read/watch. Do you have any book/movie recommendations?
WHY IT WORKS: You’ll find out which genres he’s into, and then this can snowball into a conversation about each of your favourite books, films, and other cultural mediums.
You: What’s your favourite thing about where you grew up?
WHY IT WORKS: This is a great way to get some insight into where he came from, even if he isn’t crazy about the said place. You’ll be able to learn more about his adolescence, his family, and some fond memories.
You: What do your weekdays/weekends usually look like?
WHY IT WORKS: You’ll get some answers about his work/life balance and how he not only spends but prioritizes his spare time.
What to say to a guy over text examples
Alas, some texting ideas that’ll be sure to yield positive results.
You: Hey, I have a busy week ahead of me but would love to try to meet up after work one night. Let me know what your availability looks like
WHY IT WORKS: This lets him know that you have plans and priorities but can still accommodate him. If you appear too available, it might read as desperate.
You: I got tickets for [an event that he would be interested in], wanna join?
WHY IT WORKS: Present an offer he can’t—or won’t want to—refuse. Your kind gesture will make his day.
You: [New restaurant, bar, museum, gallery, etc.] just opened—we should check it out soon
WHY IT WORKS: This will (hopefully) lead to plans and something you’ll both to look forward to!
You: I’m doing [something you’re passionate about] this weekend. You should join 😄
WHY IT WORKS: While catering to his interests is important, don’t be afraid to invite or introduce him to your world of passions, hobbies, and extracurriculars. (Plus, it’ll give you a chance to show off something you’re good at!)
You: Hey, do you think you could you help me with [task that he’s exceptional at]?
WHY IT WORKS: Everyone loves to feel wanted, but to feel needed is even better. He’ll get to show off his skills/knowledge and enjoy the satisfaction of being useful.
What not to say to a guy over text
Because I’d be remiss to not include some examples of what not to do.
You: When can I see you next?
WHY IT DOESN’T WORK: Circling back to the concept of “appearing too available or desperate,” this question reads as if you want to pencil him in as soon as possible. Not a cute look.
You: What are we?
WHY IT DOESN’T WORK: “What are we?” is a loaded question. Yes, this conversation may eventually need to be had, but it should take place in person to avoid miscommunication(s).
You: Are you seeing other people?
WHY IT DOESN’T WORK: There will be a point where this question is also appropriate to ask (i.e., when you’ve become physically intimate, or you’ve developed feelings), but this discussion, too, should happen face-to-face.
You: Who’s that girl in [picture on his desk, Instagram post/story, etc.]?
WHY IT DOESN’T WORK: Even if you’re just genuinely curious, you run the risk of looking jealous and insecure. You may learn more about said girl sooner or later but try to wait for it to happen organically.
You: How do you feel about me?
WHY IT DOESN’T WORK: It’s fair to want an honest answer to this question, especially if you’ve developed feelings. This inquiry can make him feel backed into a corner, which might make him retreat altogether. Instead, pay closer attention to his actions.
Conclusion/final thoughts
There’s comfort in knowing you have various approaches to handling romantic conversations correctly, right?
Above all, remember that these conversations will serve as a litmus test for you too. Meaning, don’t ever try to act out of character to impress him or put too much effort in where it’s not reciprocated. If you feel compelled to change anything about who you are to fit a certain mould, that’s a good sign you’re simply not compatible with him.
So, just be yourself—and do so confidently.
PERSONAL INTRO:
Hey there! I’m Hanna, a New York City-based writer and one of many, many bachelorettes navigating the dating scene. In the 8.5 years that I’ve resided here, I’ve gone on dozens of dates, so I’ve had plenty of time for trial and error.
Given that phone calls have been all but phased out as a communication norm, we’ve collectively had to adapt to texting (and DMs) as primary communication with family, friends, and suitors. Thus, I’ve since applied my writing expertise to hone my texting skills. Think of effective communication, clever humour, and playful flirting.