So you’ve been dating or talking to this guy for a bit. Maybe you’ve had your first date, maybe you’ve been dating for some time, or maybe you’re working up to a first date.
Maybe you’re not even looking for a date at all, and you just want a little fun. There’s no shame in that.
Late night conversations are perfect for any of those situations. But depending on where you are in the relationship, you need to be careful of what you say or you risk overwhelming him.
What kinds of things should you text a guy a night?
We’re glad you asked. We’ll share a bunch of things to say to make sure he’s thinking about you (and only you) late into the night.
Let’s start by answering a couple quick questions, though.
Should you text a guy at night?
In short: Yes!
There’s no reason you shouldn’t. One thing to remember, though, is that late night texts, depending on where you are in your relationship, can portray a certain message.
They’re commonly associated with sexiness or loneliness. In many situations, both of those things can be fine to show, especially when you know him pretty well.
But if you’re not in an established relationship or you don’t know him well, nothing can make him grow colder than you looking needy.
So the more nuanced answer here is: yes, but exercise a little care and caution in just what and how much you text him at night.
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How late should you text him?
When it comes to talking at night, another common question is just how late can you text him?
There isn’t one clear-cut answer here that applies to everyone and every relationship. It varies.
To start with, though, establish some boundaries with a measure of logic. Don’t text him too late, especially if it’s a work night or if he’s seeming tired.
However, if you’re already talking and the conversation is just flowing naturally, there’s no reason you should stop, either.
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Things to Text a Guy at Night
The basic checkup text.
When someone asks you about your day or how you’re feeling, you feel cared about, right?
You can do the same thing for your guy. In fact, this works in both casual and more serious relationships, because it’s a classic conversation starter.
He’ll likely ask you how you’re doing in return. Otherwise, he’ll probably say something that gives you an opening to respond to.
Example: Hey, how did your day go?
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Make him laugh one more time for the day with a quick meme.
Just like you appreciate a man who can make you laugh, men like women who can crack them up.
So end the day on a high note and show him your bright sense of humor with a choice meme or picture. This demonstrates to him that you’ve got that humor so many people are looking for and has the added bonus of putting a smile on his face before bed.
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Request a pick-me-up from him by asking for one of his favorite memes.
Had a bit of a rough day?
While we recommend keeping the conversation as positive as you can in the early stages of a relationship, you can still ask him for a mood boost. Ask him to send you one of his favorite pictures or memes.
It indicates your interest in him, and it gives you another chance to see what he’s into. There are memes for all kinds of things, from games to books to movies to politics.
What he chooses to send you back will say a lot about him.
Example: “I could use a laugh. Send me one of your best memes?”
Get him on the edge of his seat with a Hollywood-worthy cliffhanger.
There’s a reason the biggest movies often end on cliffhangers. It keeps you excited for the next installment and talking with your friends and family about what might happen.
You can take this same psychological strategy and use it in your texts. If something really interesting happened to you that day, send him a brief text that doesn’t give the surprise away.
Not only will it get him opening up, but it’ll be your time to shine. Take the opportunity to demonstrate some storytelling skills worthy of the red carpet here.
Example: “You won’t believe what happened to me today...”
Get deep with it.
You’ve probably had late night conversations with your friends that kept you up almost until the sun rose. There’s something about late hours that make conversations that would be silly during the day seem extra powerful.
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Take advantage of this time. Get a deep, intriguing conversation started with your man that leads you both into crazy possibilities.
Exercise some caution here, though. Unless you’ve been together for some time and know where he stands on many things, you might want to avoid subjects that could start a debate, like politics.
While you want to be your own person and you don’t need to agree with him on everything, it will be easier for the conversation if you stick to something a little less controversial. You’ll still be able to show off your deep side while giving him the chance to show off his.
Example: “I’ve been laying here thinking about outer space a bit. Do you think we’re alone, or that there’s something else out there?”
Let him lead.
In many traditional dances, the man leads. Sometimes, a conversation is a little bit like a dance – it shows how flexible you can be and how interesting you are.
So if he’s texted you first that night, go with it. Let him lead you in this textual dance and follow his conversational cues.
He might just take you somewhere you’d have never thought to go before.
Example: Ask question to follow the conversational flow like, “And then what?” or “What did you think?”
Follow up after a successful date.
This is perfect if you’ve just seen him that day. You can show him that you’re excited to see him again.
By sending him a follow-up text after your date, you’ve also got an opportunity to be a bit flirty and cute.
Example: “I had an amazing time with you today/tonight. I’m ready for part two whenever you are.”
Turn up the heat with some sultry descriptions and selfies.
Ready to turn the heat from low to high?
You can leave your guy wondering if something’s wrong with his thermostat by sending him a hot selfie or a tantalizing description of what you’re wearing and doing.
This opens the door for a steamy late night conversation. He’ll be begging for more afterward.
It works really well for casual and long-distance relationships. In the case of a long-distance connection, it helps you soften the lack of physical contact with some delicious visuals that will make him absolutely pine for you.
Example: “Just getting ready for bed. What do you think of my pajamas?” – Then send him a picture of your sexiest PJ’s.
Dial his curiosity up to eleven.
Send him a text that’s purposefully a little vague to snare his attention. By leaving out some details, you’ll give yourself some wiggle room to decide how you want to the conversation to go.
Want to leave him salivating over you? Use this method to lead him into some sexy fantasies.
Looking to leave a cute smile on his face? Then you can turn it into a romantic conversation centered on your sweet dreams of him.
He’ll be dying to know more. His curiosity will have him begging you for answers – and you can have a bit of fun here giving him what he’s looking for.
Example: “I had some interesting thoughts/daydreams about you today at work.”
Ask him a fun question.
Have you been in the dating game for some time now? Then you’ve probably heard the same tired, overused things over and over again.
Talking to people can get agonizingly boring. And when you talk to enough of them, they can start to blend into each other so you forget who’s who.
The last thing you want to be is forgettable. Asking a unique and fun question could lead to a conversation that will set you apart from any other woman he’s spent time with before.
If you’re not entirely sure what to say, try looking the subject online. There are all kinds of lists of unique questions to ask people you’re getting to know.
Example: “So if you woke up tomorrow with one super power, what would you pick?”
Get his recommendation.
Guys like feeling as if they’re the expert in something and love being treated accordingly. By going to him for his suggestion in something, you’re deferring to him as a sort of expert, and it’s a real ego boost.
Plus, it shows him you’re paying attention to his interests and that you value his opinion. Who doesn’t like that feeling?
Get his suggestion for the next show to watch, the next band to listen to, the next book to read, or the next restaurant to try. Then make sure you try out his suggestion and let him know what you thought of it – that way, he knows you’re taking his recommendations seriously.
Example: “I just finished this show, and I’m not sure what to watch next. Got any recommendations for me?”
Make a recommendation to him.
Hey, making recommendations is a two-way street. If you hear or see something you know he’d be into, there’s no reason why you shouldn’t let him know.
It would be boring if you were only expressing interest in everything he’s into, and it would make you look like you’re clinging to everything he does. That’s a huge turn-off.
You can broaden his horizons a bit.
Remember, this doesn’t mean to bombard him with suggestions constantly. But here and there, it’s a great way to show him some of your own interests as well as display your interest in him.
Example: “I heard this song today that I really think you’d like.” –Then send him a link to the song.
Share your (spoiler-free) thoughts about the latest developments in current events or media.
Maybe you took his suggestion for a show or music, maybe he took yours. Either way, now that you’re in together, you have the perfect chance to open up countless exchanges about what’s going on with it.
Say you’re watching a new series together. Night is the perfect time to sit back and unwind while you watch, so it’s also the perfect time to throw him a text about your latest thoughts.
Get his thoughts on the matter, too. Nothing brings people together like a good series, after all.
If he’s behind, though, keep your thoughts spoiler-free, of course.
Example: “I just watched the last episode of *show.* I can’t believe the ending! Have you seen it yet?”
Start planning out your next date.
Feeling a little bold? Why not take the time to start planning out your next date?
Taking the initiative can help set you apart from any competition. It makes you look confident, like you know exactly what you want…and you’re not afraid to go get it.
There’s a lot of pressure on guys to do all the chasing – and don’t get us wrong, being chased is fun. But sometimes doing a little of the chasing yourself relieves some of the pressure on his shoulders and makes him feel wanted.
Example: “Hey, wanna grab a coffee with me tomorrow?”
Test the waters by asking what his plans are.
Maybe you’re not feeling bold. You could be really unsure of where his head at and want to proceed with caution.
That’s okay, too. You can send a text to feel him out and determine how soon he wants to see you again.
Casually drop him a text asking what his plans are maybe a week or so in the future. If he’s really interested, he’ll get the hint and come back with an invitation for you.
Example: “What are you up to this weekend?”
Send him a cute selfie.
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Selfies don’t have to be sexy. You may even be trying to avoid that route because you don’t yet want your relationship to focus on that factor, which is perfectly fine.
Cute selfies are great, too. Snap a picture of you curled up with a pet or bundled up for the night.
A great picture has the potential to melt his heart. It may just end up saved on his phone to look at again later.
Further Reading: What to Text a Guy Before the First Date (That Will Make You Irresistible)
Ask him to send you a selfie.
Asking him for a selfie is a fun option, too. It opens up a world of possibilities and directions for you to go in.
Along with the right emoji, your request can go anywhere you want it to.
Looking for a sexy picture to make you drool? Try asking him for a picture to get you through the night with a winking face.
Want something adorable to gush over? Ask him for a picture of his handsome face with a smiling emoji.
Men like feeling attractive, too. This is a great way to show him just how attractive you find him.
If you haven’t already sent him a picture, it’s the perfect time for you to return the favor once you get his.
Example: “Mind sending me a picture? I missed seeing your handsome face today.”
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A basic (and classic) good night text.
There’s nothing wrong with going back to basics. Actually, sending a standard good night message makes you seem level-headed.
Keep it simple, but try to avoid sounding too cold. Sending just “good night,” for example, can seem really distant – which might work if you’re looking to play hard to get.
But adding some well wishes along with a good night gives your message a touch of warmth without being too clingy. If you’re not being overly flirty here, he’ll start wondering what he needs to do win you over.
Example: “I hope you had a great day. Good night!”
A sweet good night text.
Is your relationship with him starting to bloom into something beautiful?
A sweet and flirty good night message will be exactly what you need, then. You can occupy part of his mind without coming off as needy.
And if you’re lucky, sending it right before bed will help ensure you end up starring in his dreams, too.
Example: “You were on my mind all day. Maybe you’ll be in my dreams, too. Good night! :)”
A spicy good night text.
If you’re feeling a little frisky, then what you want to do is send him a late night text that ups the spice factor.
The right message will turn him on. He won’t be able to sleep, because he’ll spend his time tossing and turning all night thinking about you and imagining you.
Go all in, or just give him a little bit to tantalize him. It’s entirely up to you.
We suggest just hinting at it a bit. It’s enticing and intriguing, and it will leave him craving you like nothing else.
Example: “If you were here with me, I bet we wouldn’t be trying to sleep. Have a good night…”
To wrap things up:
If you want to build a long term relationship with a guy, it's important to understand the one thing that all men are thirsty for.
My name is Jenny and I love helping people with their relationships. I believe a few simple tips can help people massively improve their communication skills with their partners and really express themselves. Thanks for visiting!