14 Text Messages Girls Always Regret Sending To Their Guy (+ 7 That Are Foolproof)

Texting adds an element of complication to any relationship. While the rules change a little between those fresh three-month-old relationships and those two- or three-year-old relationships, there are some standards that hold no matter how long two partners have been together.

Texting is tricky because no one really tells us how to do it. Sure, we know the slang and the acronyms but, TBH, we still don’t know what the protocol is for text etiquette.

The obvious ones are there: don’t text after 1 AM, don’t send emotionally charged texts while someone is at work, and on and on. It’s a lot of don’t. However, there are some do’s as well!

Texting has huge benefits in a relationship. It can keep the flirtatious spice alive when both partners are stuck doing their boring jobs, and it can also be a way to transcend long distances.

We wanted a few more guidelines, though, which is why we went through and figured out the 14 messages we almost always regret sending to our partners; also known as the texts to delete from our minds! We also decided to throw in the 7 best messages to send, because why not work more positivity into our relationships, right?

21Stop Sending Those Single ‘Heyyy’ Messages

We love those folks who start conversations. As people who never start conversations, we’re always grateful for friends who aren’t nervous to reach out and start a chat, be it through text or instant message. However, anyone sending those “heyyy” text messages? Bolde says that this is one to quit.

The extra letters add an element of childishness. Not to mention how it’s way too easy to get lost in that loop of “hey, what’s up, not much, you?” Send a hey, but also send a little something extra to really get that conversation flowing. And skip the side order of extra letters!

20And If It’s A New Relationship, Keep Conversation Pre-Midnight

No-brainer, right? Unless the two of you have an established conversation going before the clock strikes twelve, it’s a good idea to avoid the late night messaging. Daily Urbanista lists this as one of the things that could be misleading, as well as disrespectful if he’s got an early morning ahead of him.

Respecting his schedule is important, and part of that is making sure that we’re not the reason he’s staying up late; even if he really, really wants to. Don’t forget to cap off any nighttime conversation with a good night, if you two are chatting into the wee hours. That’s something he’ll love.

19Foolproof: Compliments Are Always Awesome

Who doesn’t love compliments, right? Here’s one kind of text messaging that everyone can get behind. We personally love getting compliments. Maybe it’s just that attention loving Leo in us, but compliments always make us feel loved, special, and spark us to shine a little brighter throughout our day.

Logic dictates that he’ll feel the same way about receiving a compliment, and we have it straight from our boyfriend’s mouth that he does actually share our love of compliments. So, when in doubt, text a compliment your partner’s way. Whether the relationship is old or new he’ll no doubt appreciate the midday pick-me-up.

18Emoji-Filled Paragraphs Are A Little Awkward To Look Back On

Thought Catalog went ahead and interviewed a series of guys about texting preferences and habits, and the results were a little surprising. For instance, the emoji conundrum. One or two emojis are great. They add emotional quality and can help an ambiguous text message read more clearly.

However, “Nate, 30, says the golden rule is ‘No emojis if you are over the age of 16.’” While that’s just one Thought Catalog guy’s opinion, we do think he has a point. In the same way that extra letters can be a little childish, so can an overabundance of monkey, alien, or peach emojis.

17Sarcasm Is Hit And Miss

Remember when we mentioned that emojis can make the emotional quality of a text message a little more clear? This is especially true for those of us who are sarcastic. We’ve found that sarcasm can be hit and miss, especially if our partner isn’t someone who deals in a lot of sarcastic humor. Be careful with this one.

We’re definitely not saying to squash that sarcastic humor, but we are saying to read the text as he might read it before sending the message. If there’s anything ambiguous, add an emoji or two to clear it up. Might we suggest the cry-laugh emoji? That’s a sarcasm staple in our texts.

16Foolproof: Following Up A Date Night With A Thank You Message

The old adage used to be to wait for the guy to call, likely a day or two after the date night happened. Thankfully, instant communication means that that standard is gone, and there are no gender-specific rules regarding contact. Some people do prefer the gentleman to contact first, but it’s not a requirement anymore.

We suggest taking the lead on post-date contact, especially if it was his treat. Even in an established relationship, it’s always a good idea to reach out after a date to say thank you. Psychology Today says thanking a partner shows gratitude towards them, which will make them feel loved and acknowledged.

15All The Nitty Gritty Details About Our Life

We get it: the day was busy, the bus passed you by, and you forgot that healthy lunch you packed, forcing you to grab yet another Chipotle burrito bowl. Believe it or not, our partner doesn’t necessarily want to know all that.

Bolde backs us up on this one by saying, “he doesn’t need to know every detail about your day in a single message. If you need to tell him a lot of stuff, just call him or wait until you get together.” Besides, it’s more fun to bond over burrito bowls in person rather than through a maybe-kind-of-angry text message.

14Multiple Messages Can Be Annoying

Now, here’s one that we’re going to add a caveat to. Multiple messages can be annoying, but sending two shorter text messages is, in our opinion, much better than just sending one long one. It breaks up the ideas and makes it seem less like a tidal wave or wall of text.

Daily Urbanista explains by saying, “texts should be back and forth – a message, a reply, and so on. If you are sending double the amount of texts they are sending you then you’re trying way too hard,” which isn’t a bad thing once in a while, especially when new relationship nerves are in the mix. Just take a deep breath!

13Anything Passive Aggressive Breeds Negativity

This is one that typically comes up in longer relationships, though we’ve also seen it happen in new, blossoming relationships too. Passive aggressive text messages aren’t flattering as a general rule. Bolde reminds us that these can often be misconstrued to be meaner than they actually are, which can ultimately lead to a bigger argument at the end of the day.

It’s better to save up any negative thoughts and energies and let them out in person. It doesn’t need to be confrontational either. Sitting down and having a face to face conversation with a person is all we need to clear the air sometimes.

12Foolproof: Something Good That Happened Today

Everyone loves positivity! Believe it or not, finding something good to send a partner in the middle of the day will get a great response. Psychology Today says, “consistently initiating positive interactions makes it more likely that your relationship will survive and even thrive amidst stress, conflict, and challenges.”

This basically means that the more positive we can make our communication, the stronger our relationship will be. So go ahead: send that snap of a cute dog you got to pet, or mention getting 96% on your end of term paper; he’ll love hearing the good news, even if it doesn’t affect him at all.

11For Those That Are In The Dating Phase, Not Sending Messages Is The Biggest Regret

This isn’t technically a message that we regret sending, but it is a kind of text messaging that tends to breed regret. Thought Catalog’s interviews gave us this piece of wisdom, from a 27-year-old man called Ben, “after 2 – 3 dates, I usually stop worrying about the time or frequency of my texts as strategic, because I feel that I have a read on them and whether or not we like each other.”

So, if you’ve made it past the first couple dates, stop worrying about whether or not to hit send. Just go for it, and trust that the connection is strong.

10Anything That Stops The Conversation

When we’re talking to the (current) love of our life, it makes sense that we want to keep the conversation going. Texts that stop the conversation might feel like a mystery, but they’re actually surprisingly easy to pinpoint. Think of any of the foolproof messages we found, and then think about the opposite. Negativity, one-word responses, “LOL”… all of these are the things that are going to stop a conversation.

We personally almost always regret sending these and find that there’s a whole lot of scrambling to try and find a new conversation topic. Don’t play that stressful game, and avoid sending those one-word responses.

9Close-Ended Questions (And Answers)

Another way to stop the conversation is to send and receive close-ended messages and answers. If someone asks how your day was, don’t just say “good.” Give a little context, detail, and/or a follow-up question. Bolde mentions that those who stick to the yes or no questions and answers don’t always end up having the best conversations.

After a while, our partner tends to read one-word answers and yes or no questions as obligatory texting rather than overjoyed texting. This can negatively impact the relationship, as they might think that you’re not so incredibly excited every time their name pops up on your phone. Which, of course, you are, right?

8Poor Grammar And Unintelligible Spelling Is A No-Go

Here’s one that the gentlemen of Thought Catalog mentioned, and we’re very glad they did. “According to Cameron, 23, the golden rules are to mind your grammar and… Always use complete sentences,” which is kind of common sense, if we think about it. There’s no harm in re-reading a message for any obvious mistakes before sending it.

While we’re not saying that there needs to be perfect grammar and spelling, make sure it’s understandable between the two of you. And remember: there’s always time to proofread something. It takes 30 seconds, and you might just catch an autocorrect that changes the meaning of your whole message!

7Unresponded To Photos (Yes, It Does Happen)

Bolde mentions this in a slightly more graphic way, but generally, we’re talking about those saucy photos that are sent late at night, be they adorable under-the-sheets smile selfies or artfully angled photos. Believe it or not, him leaving those photos unresponded to does happen, especially if he’s tired or in the middle of late night studying.

It’s a little painful and is definitely something we regret sending. Not to mention how the photos are then in his hands. Basically, keep things in the heat of the moment. They’ll be better received and will ensure that we’ll get a response rather than an ignored super cute selfie.

6Foolproof: A Nice Memory You Two Share

Psychology Today reminds us that positivity is the key to a happy and successful long-term relationship. We all know that, right? The benefits of positivity are huge. But how do we achieve positivity day to day outside of smiley faces and sunshine emojis? The answer is easier than we think.

Psychology Today says that a spontaneous memory you two share is a great way to incite some happy feelings in our partner. A nice memory makes us happy, and might even plunge our partner back into that beautiful Saturday (or whenever the memory took place). That’s a great thing for stressful midweek meetings, right?

5Foolproof: Good Mornings And Goodnights

Everyone loves these messages, and for good reason! Good mornings and good nights are some of the best messages to receive across the board. Daily Urbanista points out that there’s a simple reason for this. Daily Urbanista says, “when you send a good morning text message you are basically telling the other person ‘I woke up today and you were the first thing on my mind’. Ditto for good night text messages, which say ‘I’m going to sleep and I still can’t stop thinking of you’.”

Sign us up for those kinds of texts, please! We promise we’ll always return the favor.

4Messages That Are All About Us

In an ideal world, we would be the chosen topic of conversation all the time. It’s not that we’re self-obsessed, we just find ourselves very, very interesting. Not everyone feels that way, though, and it’s been a learning curve figuring out that our partners don’t always find us as riveting a topic to talk about as we do.

Bolde reminds us to always keep the conversation balanced and to ask about his world as well as commenting on the world as a whole. There are tons of things to talk about. Music, world events, memories, upcoming dates. Anything that he has going on, of course, is also a great topic to talk about. It shows interest!

3Foolproof: ‘I’m In The Middle Of Something, But I’ll Text You Soon!’

“But wait,” you’re probably thinking, “that sounds like we’re stopping a conversation, not continuing it!” You’re absolutely right! However, this text message is always okay to send because it shows a level of respect for the communication you two have. Elite Daily inspires this one, as they’re all about clear communication.

Life gets busy. If you two were previously chatting over text message and all of a sudden you need to run off to a meeting, send this little text to let him off the hook. Believe it or not, our partners often wait with bated breath for our messages back (just like we do). Send him this so he can breathe!

2 The Dreaded Break-Up Text

This is a rough one, but we have to say it just so it’s been said. Breaking up with someone over text message isn’t the best way to go about it. Ideally, we’d do it in person. Less ideally, over the phone. The least ideal is a text message unless your safety might be at risk. In that case, we definitely do suggest keeping your distance.

If you’re thinking of breaking up with your partner, though, Bolde reminds us that breakup texts aren’t great because it’s such a casual form of communication. And for something as big and impactful as a breakup, it’s good to allow for the opportunity to talk in person.

1Foolproof: Responding To Something He’s Said

Ultimately, a response is a message we’ll never regret sending. The days of playing hard to get are over. Daily Urbanista explains, “it’s fine to wait a few hours to respond to a text if you’re busy and [we] wouldn’t recommend that you constantly drop everything to respond to a text message within minutes,” but, “don’t go out of your way to play games.”

This includes waiting days on end to respond or even sending texts at times when he’s probably not going to be looking at his phone. Just respond, and welcome the conversation that flows. That’s what a relationship is all about.


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