180+ Good Night Pick Up Lines to End the Night on a High Note

A plain “goodnight” gets the job done, but it doesn’t do much else. A good night pick up line, on the other hand, turns the last message of the day into something the other person actually thinks about as they fall asleep.

There’s a reason these lines have become such a big part of texting culture. Late-night conversations tend to feel more open and honest than daytime ones, and a well-timed message right before bed can land differently than the same line sent at noon. It’s the last thing someone reads before they close their eyes, which makes the timing part of the charm.

This kind of message has become especially common on dating apps and in the early stages of getting to know someone, where a thoughtful goodnight can do more to build interest than an entire day of small talk. It works just as well in long-term relationships, where a consistent, genuine goodnight routine becomes something both people quietly look forward to.

This guide collects 180+ good-night pick-up lines for 2026 — funny, cheesy, romantic, bold, and wholesome — along with real advice on how to pick the right one, when to send it, and how to avoid the messages that come across as try-hard instead of sweet.

What Are Good Night Pick Up Lines?

Good night pick up lines are flirty, funny, or heartfelt messages sent before someone goes to sleep, designed to leave a better impression than a simple “goodnight” or “gn.” They can be playful and joke-based, smooth and romantic, or warm and wholesome, depending on the relationship and the mood you’re going for.

Unlike daytime pick-up lines, which usually work as conversation openers, goodnight lines typically work as a closer. They’re the last message in a conversation, meant to leave someone smiling, thinking about you, or looking forward to the next time you talk.

People send goodnight pickup lines to:

• End a text conversation on a warmer, more memorable note
• Flirt with someone new without the pressure of starting a whole new topic
• Keep a long-distance relationship feeling close, even at the end of the day
• Add a little romance to an established relationship’s nightly routine
• Make a crush smile right before they fall asleep

Why Good Night Pick Up Lines Work So Well

• They land at an emotionally open moment. People tend to feel more relaxed and less guarded right before bed, which makes a genuine or playful message hit a little differently than it would earlier in the day.
• They don’t require a long reply. A good night message is easy to respond to with something short, so there’s no pressure to keep a long conversation going right before sleep.
• They show you’re thinking about them. Taking a moment to send something more thoughtful than “gn” signals that they crossed your mind, which matters more than people admit.
• They create a nightly habit. Regularly sending a sweet or funny goodnight message can become a small ritual that strengthens a connection over time.
• They work at every relationship stage. Whether you just started talking or you’ve been together for years, a good night line adapts to fit the moment.

Timing plays a bigger role in these messages than people usually realize. A goodnight text sent right as the conversation naturally winds down tends to feel far more genuine than one sent out of nowhere in the middle of the day, relabeled as a “goodnight.” The context of actually being close to bedtime is part of what makes the message land.

It also helps to think about good night lines as punctuation on the day’s conversation rather than a fresh opener. A funny joke earlier in the day pairs well with something equally lighthearted at night, while a more emotional conversation might call for a softer, more sincere close instead.

Good Night Emojis and How to Pair Them

 

 

Emojis can add warmth to a good night text without making it feel over the top, as long as they’re not overused. Here’s a quick guide to pairing tone with the right emoji.

Emoji	Best Paired With
	Simple, sincere goodnight messages
	Funny or sleepy-themed lines
	Sweet, cheesy, or romantic lines
	Bold or flirty lines
	Wholesome or caring messages
	Romantic lines referencing dreams or stars

A general rule worth following: stick to one or two emojis per message. Overloading a good night text with emojis can undercut a sincere or bold line by making it feel less genuine.

Types of Good Night Pick Up Lines: Quick Overview

Category	Best Used For	Vibe
Funny	Early-stage texting, keeping things light	Playful, easygoing
Cheesy	Flirty texting, casual crushes	Warm, lighthearted
Romantic / Sweet	Established relationships, deeper connections	Genuine, heartfelt
Bold / Flirty	When there’s already mutual interest	Confident, direct
Wholesome	Any relationship stage, comforting tone	Caring, gentle
Situational	Long distance, new relationships, after a date	Tailored, specific

Funny Good Night Pick Up Lines

Humor is one of the easiest ways to end a conversation on a high note. These lines are perfect for someone you’ve just started talking to, or anytime you want to keep things light before bed.

1. Goodnight. I’d count sheep, but I’d rather just keep thinking about you instead.
2. I’m not tired, I just can’t sleep until you say goodnight back.
3. My pillow is jealous because I keep thinking about you instead of actually sleeping.
4. I’m filing an official complaint; you’re taking up way too much space in my brain tonight.
5. If you show up in my dream tonight, please don’t charge rent.
6. I’m not saying you’re the reason I’m still awake, but it’s suspicious.
7. Goodnight. My phone battery is dying faster than my ability to stop thinking about you.
8. I tried to fall asleep an hour ago, but my brain had other plans involving you.
9. Fair warning, if I dream about you tonight, I’m blaming this conversation entirely.
10. Goodnight. My sleep schedule officially needs your permission before it starts.
11. I was going to sleep early, but then you texted and ruined that whole plan.
12. If dreams had a guest list, you’d already be at the top of mine tonight.
13. I don’t need to count sheep, I’ve got you stuck in my head instead.
14. Goodnight. Somehow, thinking about you is more effective than melatonin.
15. My bed is comfortable, but this conversation is making it very hard to leave.
16. I’m blaming you if I’m tired tomorrow; this conversation was worth losing sleep over.
17. Goodnight. I hope my texts haunt your dreams in the least creepy way possible.
18. I set an alarm for tomorrow, but honestly, I’m mostly looking forward to texting you again.
19. If overthinking burned calories, tonight would count as a full workout thanks to you.
20. Goodnight. My phone light is the only thing standing between me and actual sleep right now.
21. I’m convinced my pillow is judging me for texting instead of sleeping.
22. Goodnight. I’ll be dreaming, but no promises about who’s going to be in it.
23. I was ready for bed twenty minutes ago, then this conversation happened.
24. My eyes are heavy, but apparently my thumbs still have energy to keep texting you.
25. Goodnight. I hope your dreams are at least half as entertaining as this conversation.

Cheesy Good Night Pick Up Lines

Sometimes cheesy is exactly the right call. These lines lean into classic, over-the-top romantic charm, and they work well for flirty texting or an established crush.

1. Goodnight, gorgeous. If I could rearrange the alphabet, I’d put U and I together.
2. I’m not a magician, but every time I close my eyes, I somehow still see you.
3. If kisses were snowflakes, I’d send you a blizzard tonight. Sweet dreams.
4. I’m not a photographer, but I can already picture us together, even in my dreams.
5. Goodnight, beautiful. Even the stars are a little jealous of your smile tonight.
6. I hope your dreams are as sweet and amazing as you’ve been to talk to today.
7. Sleep tight, because tomorrow you might just wake up thinking about me.
8. Close your eyes, I’ll meet you in the dream where we’re already unstoppable together.
9. Goodnight. You’re the sweetest thought currently taking up space in my mind.
10. Sleep well knowing someone out here is smiling because of you right now.
11. Goodnight. I hope your dreams include all your favorite things, and maybe me too.
12. If the moon could talk, it would probably agree that you’re the best part of tonight.
13. Goodnight, sunshine. Somehow that nickname works even at midnight for you.
14. I hope you drift off feeling exactly as good as you made me feel tonight.
15. Sleep tight, I’ll be here tomorrow, still thinking about this conversation.
16. Goodnight. You’ve officially become my favorite way to end a day.
17. I hope your pillow is soft and your dreams are just a little bit about me.
18. Sweet dreams, I promise tomorrow’s conversation is already something I’m looking forward to.
19. Goodnight. If comfort had a face, I think it would look a lot like your smile.
20. I hope you sleep like someone who knows they’re appreciated, because you definitely are.

Romantic and Sweet Good Night Pick Up Lines

These work best in an established relationship or once real chemistry has already built up. They lean sincere rather than jokey, and they hit harder because of that honesty.

1. Goodnight. I fall asleep more easily knowing this conversation happened today.
2. I don’t need a reason to think about you before bed, but tonight I’ve got plenty.
3. Goodnight. You’ve made today better just by being part of it.
4. I hope you know how much easier you make even an ordinary day feel.
5. Sleep well, knowing you’re the last thing on my mind tonight, and I mean that.
6. Goodnight. I like that talking to you has become the best part of my routine.
7. I don’t say this enough, but conversations with you make the whole day feel worth it.
8. Goodnight. I hope tomorrow gives us just as good a reason to talk as today did.
9. I like ending my night knowing you’re somewhere out there doing the same.
10. Goodnight. You’ve got a way of making ordinary moments feel a little more special.
11. I hope you fall asleep feeling as appreciated as you make me feel every day.
12. Goodnight. I’m grateful this conversation happened, even the small parts of it.
13. I don’t need grand gestures, just nights like this where talking to you feels easy.
14. Goodnight. I hope your dreams are peaceful, and I hope I get a small place in them.
15. I like that even a simple goodnight text to you feels like it means something.
16. Goodnight. Thank you for making today feel lighter just by being part of it.
17. I hope you sleep well knowing someone out here genuinely values this connection.
18. Goodnight. I’m already looking forward to whatever tomorrow’s conversation turns into.
19. I don’t take these little moments for granted, so goodnight, and thank you for today.
20. Goodnight. I hope you carry today’s good parts with you straight into your dreams.

Bold and Flirty Good Night Pick Up Lines

These lines work best once there’s already mutual interest or an established connection. They’re more direct, so it’s worth reading the mood of the conversation before sending one.

1. Goodnight. I’ll be dreaming about you, and I’m not even going to pretend otherwise.
2. I don’t usually admit this so directly, but you’re the reason I don’t want tonight to end.
3. Goodnight. If you show up in my dreams, don’t expect me to complain about it.
4. I can’t promise what I’ll dream about, but I can promise it involves you.
5. Goodnight. I’ve been thinking about you way more than I probably should admit.
6. I don’t scare easily, but this conversation has me a little more nervous than usual.
7. Goodnight. Consider this my admitting I don’t want to stop texting you yet.
8. I’ll be honest, falling asleep is going to be harder than usual tonight because of you.
9. Goodnight. I’m not saying I like you, but I’m also not saying I don’t.
10. I don’t send this kind of message to just anyone, so take that as the compliment it is.
11. Goodnight. If confidence were a currency, this text alone would make me rich.
12. I don’t usually text first before bed, but tonight I made an exception for you.
13. Goodnight. I’ve got a feeling you’re going to be the reason I sleep with a smile.
14. I’m not usually this forward, but you’ve got me rethinking that approach entirely.
15. Goodnight. I’d say sweet dreams, but honestly, I hope they’re a little more than sweet.

Good Night Pick Up Lines for Texting and Dating Apps

Texting calls for something short, easy to respond to, and not too intense right before someone falls asleep. These work well for dating apps, new matches, or the early stages of getting to know someone.

Situation	Example Line
End of a good first conversation	This was easily the best part of my day. Goodnight, talk soon?
After a fun back-and-forth	Okay, going to force myself to sleep now before I keep texting you all night.
Early flirty stage	Goodnight. Fair warning, you might be showing up in my dreams tonight.
Reviving a slow conversation before bed	Random thought before I sleep: what’s the last thing that made you laugh today?
Confident closer	Goodnight. I don’t say this to everyone, but talking to you today was genuinely the highlight.

A few more good night lines built specifically for texting and dating apps:

1. “Okay, I have to force myself to put my phone down now. Goodnight, this was fun.”
2. “I wasn’t planning on staying up this late, but I don’t regret it one bit. Goodnight.”
3. “Goodnight. I already know I’m going to be checking my phone way too early tomorrow.”
4. “This conversation made falling asleep a lot harder than usual. Goodnight.”
5. “I don’t usually text this late, but I’m glad I made an exception tonight. Goodnight.”
6. “Goodnight. I’m setting an alarm mostly so I have an excuse to text you again tomorrow.”
7. “I read this back and realized I’ve been smiling at my phone for the last ten minutes. Goodnight.”
8. “Goodnight. If today’s conversation was any indication, tomorrow’s going to be even better.”
9. “I don’t know how you made a random Tuesday feel this good, but goodnight and thank you.”
10. “Goodnight. I’m calling it a night before I say something I can’t take back.”

Good Night Pick Up Lines for Her

These lines lean slightly more romantic and are built to make a girl feel genuinely thought about, not just complimented generically.

1. Goodnight to the girl who somehow made today better without even trying.
2. I hope you sleep as peacefully as you made me feel talking to you tonight.
3. Goodnight. You’ve got a way of making even a simple conversation feel special.
4. I hope your dreams are as good as the conversation we just had.
5. Goodnight, beautiful. I mean that in every sense, not just how you look.
6. I hope you know how much brighter you made today just by being part of it.
7. Goodnight. You’re easily the best conversation I’ve had in a long time.
8. I like that talking to you has quickly become something I look forward to every day.
9. Goodnight. I hope you fall asleep feeling exactly as appreciated as you deserve.
10. I don’t say this to just anyone, so goodnight, and thank you for today.
11. Goodnight. Somehow, even a bad day feels better once I get to talk to you.
12. I hope you sleep well knowing someone out here is genuinely glad you exist.
13. Goodnight. You’ve got a way of making ordinary conversations feel worth remembering.
14. I like ending my night knowing this conversation happened. Sleep well.
15. Goodnight. I’m already looking forward to talking to you again tomorrow.

Good Night Pick Up Lines for Him

These lines lean slightly more confident and playful, which tends to work well for texting a guy without sounding overly formal.

1. Goodnight. You made today way more interesting than it had any right to be.
2. I hope you sleep well knowing you were the best part of my day.
3. Goodnight. I don’t usually admit this, but I’ve been looking forward to this conversation all day.
4. I like that talking to you is this easy. Good night, and thank you for today.
5. Goodnight. You’ve got a way of making conversations feel less like small talk and more like something real.
6. I hope your night is as good as this conversation was.
7. Goodnight. I’m already thinking about what we’re going to talk about tomorrow.
8. I don’t say this often, so take it seriously: today was a good day because of you.
9. Goodnight. You’ve officially made your way into my nightly routine, and I’m okay with that.
10. I hope you sleep well, and I hope tomorrow gives us a reason to talk just as well as today did.
11. Goodnight. I like that even a simple conversation with you doesn’t feel simple at all.
12. I’m calling it a night, but I’m not calling this conversation over anytime soon.
13. Goodnight. You’ve got a way of making me smile at my phone like an idiot.
14. I hope you know how much better you made today, even from a distance.
15. Goodnight. I’m genuinely looking forward to seeing what tomorrow’s conversation turns into.

Wholesome and Caring Good Night Messages

Not every good night message needs to be flirty. These wholesome lines work well for any relationship stage, especially if someone’s had a rough day and needs something gentler.

1. Goodnight. I hope you fall asleep feeling calm and genuinely happy tonight.
2. I hope tomorrow is kinder to you than today was. Sleep well.
3. Goodnight. Take all the good parts of today with you into your dreams.
4. I’m glad we talked today. I hope you drift off feeling appreciated.
5. Rest well tonight; tomorrow’s going to need your energy, and you deserve the rest.
6. Goodnight. Sending you calm thoughts and an easy night’s sleep.
7. I hope your dreams feel as safe and warm as you deserve them to.
8. Sleep peacefully tonight, and please remember to take care of yourself.
9. Goodnight. I hope your mind feels a little more at peace before you sleep.
10. I hope your pillow is comfortable and your thoughts are quiet tonight.
11. Goodnight. Don’t forget that you matter, even on the hard days.
12. I hope you wake up tomorrow feeling lighter than you did today.
13. Goodnight. This conversation felt worth having, and so do you.
14. Sleep easy tonight, and know that someone’s genuinely glad you’re okay.
15. Goodnight. I hope tonight brings you the rest you actually need.

Good Night Pick Up Lines for Specific Situations

Different relationship stages and circumstances call for different tones. Here’s a quick breakdown of good night lines built for specific moments.

Long Distance Relationships

1. Goodnight from my time zone to yours. I hope the distance feels a little smaller tonight.
2. I hate that I can’t say this in person, but goodnight, and I miss you already.
3. Goodnight. Counting down the days until this distance isn’t a factor anymore.
4. I hope you know that even miles away, you’re still the last thing I think about.
5. Goodnight. Wish I could actually say this to your face instead of through a screen.

New Relationships or Early Talking Stage

1. Goodnight. Still figuring this out, but I already know I like where it’s headed.
2. I don’t want to move too fast, but I also don’t want to stop talking to you. Goodnight.
3. Goodnight. It’s early, but this already feels like it’s worth paying attention to.
4. I’m genuinely curious where this goes, and that’s a good feeling. Goodnight.
5. Goodnight. I like that I’m already looking forward to your good morning text.

After a Great Date

1. Goodnight. Today was easily one of the best days I’ve had in a while.
2. I don’t want to overstate it, but that might have been one of my favorite dates ever. Goodnight.
3. Goodnight. I’m already trying to figure out when I get to see you again.
4. I had a genuinely great time today, and I hope it showed. Sleep well.
5. Goodnight. Thank you for today, I mean that more than the text probably shows.

When They Haven’t Replied Yet

1. Goodnight, whenever you see this. Hope your day went well.
2. No pressure to reply tonight, just wanted to say goodnight before I crash.
3. Goodnight. Talk whenever you’re free, no rush at all.
4. Hope you’re having a good night, whatever you’re up to right now.
5. Goodnight. Thinking of you, reply whenever it works for you.

Good Night Pick Up Lines Based on Your Personality

The best good night message is the one that actually sounds like you. Forcing a style that doesn’t match your normal texting voice usually comes across as stiff or scripted. Here’s how to adjust based on your own personality.

If You’re Naturally Quiet or Reserved

Short, sincere lines tend to work better for you than elaborate jokes. A little honesty goes a long way.

1. Goodnight. I don’t say much, but today’s conversation stuck with me.
2. I’m not great with words, but I wanted to say goodnight properly tonight.
3. Goodnight. This isn’t something I usually do, but I wanted you to know I was thinking of you.
4. I don’t send messages like this often, so take it as the compliment it is. Goodnight.
5. Goodnight. Simple, but I mean it more than it probably sounds.

If You’re the Naturally Funny, Outgoing Type

Lean into your usual humor instead of toning it down for a goodnight text. It’ll feel more genuine that way.

1. Goodnight. I’d write something more clever, but my brain already clocked out an hour ago.
2. Fair warning, I’m blaming you for every yawn I have tomorrow morning.
3. Goodnight. My phone is basically begging me to put it down at this point.
4. I promise I’m funnier in person, but this is my best material at midnight.
5. Goodnight. If sleep deprivation had a face, it would look a lot like me right now.

If You’re Confident and Direct

Skip the buildup and say exactly what you mean. Confidence tends to land well in a goodnight text, as long as it still feels genuine.

1. Goodnight. I don’t overthink these messages, and I’m not about to start now.
2. I like talking to you, plain and simple. Goodnight.
3. Goodnight. No clever line here, just an honest one: today was a good day because of you.
4. I don’t do subtle very well, so I’ll just say it: I’m looking forward to tomorrow. Goodnight.
5. Goodnight. I say what I mean, and I meant every part of today’s conversation.

Good Night Pick Up Lines for Social Media Captions and Stories

Sometimes a good night message isn’t sent directly; it’s posted as a story or caption for someone specific to see. These work well for that context.

1. Ending the night grateful for conversations that actually matter.
2. Goodnight to whoever’s been making my days better lately, you know who you are.
3. Some nights just feel better because of who you talked to during the day.
4. Signing off for the night, but this conversation is staying on my mind.
5. Goodnight. Today had one really good part, and it wasn’t even close.
6. Ending the day with a smile I can’t fully explain, and I’m not going to try to.
7. Goodnight to the person who somehow made an average Tuesday feel like something worth remembering.
8. Some conversations are worth losing a little sleep over. Tonight was one of them.
9. Goodnight. Grateful for good timing and even better conversations.
10. Ending the night the same way it started, thinking about the same person.

Matching Your Good Night Line to the Relationship Stage

If you’re ever unsure which category fits best, use this table as a quick reference for matching tone to where things actually stand.

Relationship Stage	Recommended Tone	Example Approach
Just matched or recently met	Light and funny	Keep it playful, avoid anything too intense
A few weeks of talking	Cheesy or lightly flirty	Show interest without overcommitting
Established relationship	Romantic or wholesome	Lean into sincerity and consistency
Long distance	Romantic with reassurance	Acknowledge the distance directly
After a great date	Warm and appreciative	Reference the date specifically
They haven’t replied recently	Low-pressure and casual	Avoid guilt-tripping or over-explaining

Reading the actual stage of the relationship, rather than defaulting to the boldest or cheesiest line available, is usually what separates a message that lands well from one that feels mistimed.

How to Send a Good Night Pick Up Line Like a Pro

A great line only works if the timing and tone match the moment. Follow these steps to make sure your message lands the way it’s meant to.

1. Match the tone to the relationship stage. A funny line works better for someone new, while a sincere one fits an established connection.
2. Don’t overthink the timing. Send it whenever it feels natural in the conversation, rather than forcing it at a specific hour.
3. Keep it short. A good night message doesn’t need to be long to feel meaningful. One or two sentences are usually enough.
4. Read the mood of the conversation. If the day’s texting has been serious, a lighthearted joke might feel out of place.
5. Don’t expect an immediate reply. Good night messages are often the last text of the night, so there’s no need to wait anxiously for a response.
6. Personalize when you can. Referencing something specific from the day’s conversation makes the message feel less generic.
7. Stay consistent, not repetitive. If this becomes a nightly habit, vary the wording so it doesn’t start to feel copy-pasted.

Common Mistakes to Avoid With Good Night Pick Up Lines

Do This	Avoid This
Match the tone to how well you know them	Sending an overly bold line to someone you just met
Keep it short and genuine	Writing a long paragraph right before bed
Personalize based on the day’s conversation	Copy-pasting the same line every night
Send it naturally, without pressure	Demanding a reply or getting upset if they don’t respond
Read the mood of the day	Sending a joke when they’ve had a rough day
Stay authentic to your own tone	Using lines that don’t sound like your normal texting style

Building Real Connections Beyond the Lines

A clever good night message is a nice touch, but it’s not what actually builds a relationship. If you want these messages to mean something long-term, keep these habits in mind:

• Consistency matters more than cleverness. A simple, genuine goodnight sent regularly builds more trust than one elaborate message sent once.
• Read their responses, not just your own message. If they seem distant or don’t respond well to flirty lines, dial it back and keep things simple.
• Don’t rely on texting alone. Good night messages work best as part of a relationship, not as a replacement for real conversation and time spent together.
• Be willing to just say goodnight sometimes. Not every message needs a clever line attached. Sometimes simple is exactly right.
• Pay attention to their day. A goodnight message that acknowledges something specific about their day will always land better than a generic template.
• Notice patterns over time. If certain types of lines consistently get a warmer response, that’s useful information about what actually resonates with this specific person.
• Balance effort on both sides. A healthy dynamic usually involves both people occasionally initiating the goodnight message, not just one person carrying out the routine every night.

Good night pick up lines are a small gesture, but small gestures repeated consistently are often what actually build closeness over time.

Frequently Asked Questions

What are good night pickup lines?

They’re flirty, funny, or heartfelt messages sent before bed, designed to leave a better impression than a plain “goodnight” text.

Do good night ppick-uplines actually work?

They tend to work well because people are more emotionally open at night, making a thoughtful or playful message land more effectively than usual.

What’s the best goodnight pickup line for someone new?

A short, funny line tends to work best in the early stages, since it keeps things light without feeling too intense too soon.

Should I send a goodnight text every night?

It depends on the relationship — a nightly message can build a nice routine, but it should feel natural rather than obligatory.

What if they don’t reply to my good night text?

Don’t read too much into it. People often see these messages the next morning, and a lack of an immediate reply usually isn’t personal.

Are romantic good night lines only for established relationships?

Mostly yes, since sincere lines tend to land better once there’s already some trust and chemistry built up.

Is it okay to reuse the same good night line more than once?

Occasionally reusing a favorite is fine, but varying the wording keeps the gesture from feeling repetitive or copy-pasted.

What’s the best emoji to pair with a good night pick-up line?

It depends on tone — a moon or stars emoji suits sincere messages, while a wink or sleepy-face emoji fits funnier or bolder lines.

Should I send a good night text if we argued earlier?

A short, sincere message can help soften tension, but it’s usually better to address the actual disagreement rather than relying on the text alone to fix it.

Final Thoughts

Good night pick up lines are a small, easy way to end a conversation on a warmer note than a plain “goodnight.” Whether you go funny, cheesy, romantic, or wholesome, the right line shows the other person that they crossed your mind before you fell asleep.

Pick a few lines from this list that actually sound like you, personalize them when you can, and don’t be afraid to keep it simple on the nights that call for it. In the end, consistency and genuine care will always mean more than the perfect wording, but a good line certainly doesn’t hurt either.

Before you hit send, run through this quick checklist:

• Does this match how well you actually know this person?
• Is it short enough to read comfortably right before bed?
• Does it sound like something you’d genuinely say, not a copied script?
• Does it fit the mood of today’s conversation?
• Would you personally smile if someone sent this to you?

If most of those check out, you’re already sending a better goodnight than most people bother to write.