​The Right Way And The Wrong Way To Text Your Crush

So, you finally plucked up the courage to slide into your crush's DMs. Those butterflies in your stomach are doing a silly dance that's leaving you feeling slightly queasy but also stupidly excited — you are so ready to get the conversation going. You pick up your phone and start texting away, only to delete your message and rewrite it. After doing this a few times, you're wondering whether social media has killed your ability to communicate like a normal human being. Even asking your friends to write your messages for you is starting to look like a plausible option. But you can't rely on your squad to always be there to craft the perfect message for you. Let us help by offering you the tools to be a confident communicator all on your own.

Texting your crush can be a daunting undertaking. You want to put your best foot forward while still being authentic. You want to appear interested but not desperate, and you definitely want to flirt in a way that's not cringe. It can be so hard not to overthink these conversations, so that's why we asked some of our top dating and relationship experts for advice. Get ready to text away with confidence and land that first date in style. You can thank us later.

The first rule of texting your crush is simple, but can also be the hardest to do: Don't overthink it. "When you text 'a book,' that shows that you're definitely overthinking and can come off as acting too serious," matchmaker and CEO of Exclusive Matchmaking, Susan Trombetti, tells the List exclusively. Trombetti also warns against inundating your crush with several texts. "Just text once, and if they respond right away, it's okay to text back. If they don't, wait to see if they answer at all and when," Trombetti advises. Once you've sent that text, take a deep breath and ... wait. Your best bet is to be patient and see what happens. "It's important to give the conversation room to breathe. If they haven't responded yet, resist the urge to double-text right away," dating and relationship coach Nicole Haley tells The List.

If you've managed to avoid double-texting and they've responded, Trombetti says that the ball is in your court to keep the conversation going. "Make sure to keep up some texting momentum; after all, texting can be a building block in a relationship and if you do it correctly, you can pique someone's interest. It can prime you for a great first date," Trombetti notes. While you might be tempted to respond to your crush's text the second you receive it, it's usually wise to not always answer immediately — it might come across as if you have nothing better to do or are a little desperate, which is never a good look. So text back in a timely manner but resist the urge to be a quick responder. An easy way to not overthink this (because we know you already are) is to simply treat their texts the way you would anyone else's.

You might be tempted to know who your crush voted for in the 2024 election or what their stance is on some very controversial topics, but this is definitely not something you want to get into over the phone, Exclusive Matchmaking CEO Susan Trombetti warns. "There should be nothing sad, political, or religious. You just want to be light, happy, and/or flirty along with short texts unless they start engaging, in which case, answer back," Trombetti advises. Relationship therapist Rachel Sussman agrees, telling The List that sticking to simple topics is your best bet in the beginning stages of your texting relationship with your crush. That doesn't mean you need to try and hide who you are — Sussman says to simply be your glorious self and show off your best qualities.

Of course, there might be days where putting your best self out there will feel like a sham, especially if you had a really bad day. Do you get to tell your crush about it? Well, it really depends on how long you've been texting, and you shouldn't expect them to have the answers to your problems, given that they don't know you that well yet. Clinical psychologist Beverly Palmer, Ph.D., told Women's Health that venting to your crush could be a beneficial move — it will show you how well they listen and whether they are a sympathetic person, and if they aren't, you at least know you can stop wasting your time texting them.

When texting with your crush, you might be tempted to play a little hard to get, just to make them work for it a little, but that's a rookie dating mistake you want to avoid at all costs. "Playing games on text by not answering them back is the wrong way," matchmaker Susan Trombetti cautions. Evolutionary biologist Dr. Mairi Macleod told Cosmopolitan that, mostly, playing hard to get is a big old waste of time. "If you pretend that you are happy to be casual and unattainable, then you'll most likely attract an avoidant person, and then when you decide you do want to reveal that you'd like a committed relationship, they'll be running fast in the other direction," Dr. Macleod warns. Playing games might make you feel in control of things, but it most likely won't lead to a meaningful relationship, so if you really want to get to know your crush better, just be honest and upfront.

It's easy to make it look as if you're playing games when you take forever to reply to your crush's text messages. Of course, you can't be expected to be glued to your phone all day. Trombetti suggests you be upfront with your possible future bae about why your response times might be lengthy. "If you can't continuously text because you are working, just say so after you exchange a few and promise to flirt back with them later," Trombetti advises. Relationship therapist Rachel Sussman adds that constantly texting with your crush isn't a good thing anyway. You're just getting to know each other — no need to be joined at the hip this early in your acquaintance.

If you and your crush were getting along like a house on fire over the phone and they suddenly stop texting you, it might feel like you're getting ghosted. A dating mistake we all tend to make in these situations is asking them point blank what the heck is up. But our experts say this shouldn't be your go-to move. "Don't act offended," matchmaker Susan Trombetti urges. "Don't say: 'I haven't heard back and it's rude' or 'You haven't texted me back, so I take it you aren't interested.'" 

Instead, Trombetti says to take it in stride and be in control of the situation, but don't make your crush feel like you're pressuring them into anything. Trombetti suggests sending a fun flirty text like, "There's a Bolo out on you, and I thought I would text you and give you a heads up. You can hide out at my place if you'd like" or "Thought I would say hi. Let me know if you want to meet for a drink!"

Dating and relationship coach Nicole Haley notes that, if you're always the one sending check-in texts when your crush seems to disappear off the face of the earth, it might be a sign that you need to take a step back and see if they restart the conversation for a change. This will give you an idea of how invested they really are. Relationship therapist Rachel Sussman insists on a more aggressive approach and suggests refraining from texting them if you haven't heard back in a while. "If you've made it apparent that you're interested — sit back and see who they really are. If your crush isn't being communicative, maybe you need to pay attention to what that means," Sussman says.

A big texting no-no is reaching for your phone with plans to hit up your crush when you've had one martini too many. You've seen this in the movies, and it never ends well. "Oftentimes when people are inebriated or they're under the influence of a substance, they may make decisions that they would not make otherwise," licensed marriage and family therapist, Saba Harouni Lurie, LMFT, told Women's Health. 

So, no matter how tempting it might be to flirt with your crush while you're high on alcohol-fueled courage, stay out of your messaging app and call a friend instead. "It just becomes so much more difficult to really trust your gut and to know what your intentions are when you're not able to think as clearly as you would when you're sober," Luri explained, adding that, if you're still feeling like sending that bold message to your crush the following morning, you're good to go, but you'll save yourself a lot of embarrassment by sobering up first.

We all know that infuriating feeling when someone texts us asking something mind numbingly boring, like "what are you doing?" or a simple, "Hey, what's up?" This phenomenon is known as dry texting, and dating and relationship coach Nicole Haley says these kinds of texts are a surefire way to end what could have become a meaningful conversation. "It can come across as low effort. Instead, make your texts specific or tied to something they can engage with," Haley suggests.

A good way to keep the conversation interesting is to ask your crush fun questions about themselves without being too intrusive. You can start with something simple, like enquiring about their favorite celebrity or role model, their star sign, their go-to methods for relieving stress, and their pet peeves. This not only keeps them talking and shows you're really interested in them, but it also gives you an opportunity to get to know them better. The main thing to keep in mind is to ask questions that warrant a decent answer — try to avoid yes or no questions since they tend to be instant conversation killers.

It can sometimes be difficult to completely gauge someone's personality over text, especially if they're lazy texters. Don't let this be you — texting is an excellent opportunity to showcase your personality to your crush if you do it right. CEO of Exclusive Matchmaking, Susan Trombetti, suggests you show off your witty and flirty side with texts like, "I saw 'The Notebook' last night and Ryan Gosling has nothing on you." While flirting is fun, you don't want to go too heavy on these types of texts either because it might come across as a little overbearing, especially early in your texting relationship. Follow your gut, keep it light, and (reasonably) flirty.

When it comes to emojis, use them sparingly, relationship therapist Rachel Sussman says. Matchmaker Susan Trombetti agrees, adding, "Use emojis but not too many since you are an adult, but a smiley face at the end of 'Have a great day' or blowing a kiss emoji at the end always works."

"Playful banter, light humor, or sharing a funny meme can be great ways to build rapport," dating and relationship coach Nicole Haley says. Haley suggests texting your crush something fun, like "I just saw a dog wearing sunglasses, and I immediately thought, 'This guy knows how to live.' What's the most ridiculous thing you've seen today?" Haley says these kinds of texts are great to show someone your fun side without being too serious or flirty, and it takes the pressure off them to respond in a specific way. Another way to build a deeper and more personal connection with your crush is by sending them voice messages. "It lets them get a deeper sense of who you are through your tone and expression," Haley says.

Communication is key in a relationship, and listening is a huge part of that. You and your crush might not be officially dating yet, but showing them you're a good listener can give you plenty of brownie points. There are certain questions you should be asking your crush to get to know them better, and if you take care to remember the answers, it'll show them that you don't just care about them on a superficial level — not to mention that their answers can often be great conversation starters. "Research shows asking personal and thoughtful questions is the best way to get to know someone, so don't be afraid to ask follow-up questions to get past the small talk and into a more personal conversation, Hinge Director of Relationship Science, Logan Ury, told Women's Health.

One way to show your crush that you're listening to them is by checking in about things they previously told you, dating and relationship coach Nicole Haley says. "If they told you they love hiking, you might text, 'I remember you said you love hiking — any favorite spots I should know about?' It shows you're listening and genuinely interested, which builds a stronger connection," Haley explains.

It can be confusing to decode messages from your crush, but relationship therapist Rachel Sussman says that sexual messages early in the texting relationship is a major red flag. "It's okay to be flirty but not okay to be sexual," Sussman notes. Online dating expert Carmelia Ray agrees. "You want to absolutely avoid statements that are sexually explicit in nature unless that is your only goal," Ray told Brides. 

Sexting your crush early on is risky for a myriad of reasons — you likely don't know them well enough to gauge whether or not they might share your flirty messages or even nudes you sent them with friends (or the entire internet, for that matter). Save sexting for when you and your crush have been texting a while and are comfortable with each other — the last thing you want to do is send them a nude photo when they're not ready for it.

Faulty grammar might not be one of your pet peeves, but it might very well be considered a red flag by your crush, especially if they're a grammar nerd. Give text messages to your crush a good once-over before hitting send. "Pay attention to cadence, language, even grammar. You can learn a lot about someone even in basic communication," relationship therapist Rachel Sussman says.

Even if you consider yourself a sound speller, it won't do any harm to reread your messages before sending them. Oftentimes, spell check simply wants you to fail and will end up turning your message into a rather embarrassing one (if you know, you know). Something else to avoid is adding "haha," "hehe," or "LOL" at the beginning and/or end of every single message. This gets annoying fast and might make you seem, er, a little childish.

While flirting with your crush over text is certainly fun, you'll want to move the relationship off screen eventually, such as talking on the phone or doing a video call. It's a foolproof way to prevent texting from destroying your relationship and to see whether you and your crush are compatible in a verbal interaction. "Texting can lead to a lot of misunderstanding," dating and relationship coach Nicole Haley advises. "So, it's better to use texting as a short segue to getting on the phone or meeting in person. If you rely solely on text to get to know someone it can create a false sense of intimacy."

Board-certified psychotherapist and mediator, Kimberly Key, Ph.D., agrees. "Text is probably the worst form of communication to rely on when building a relationship," Key wrote in an article published by Psychology Today. Texting too much or for too long before meeting up in person can leave things feeling very awkward on that first date, so don't procrastinate for too long on arranging a call or meeting up face to face.

Much like Rose eventually had to let Jack go in "Titanic," you, too, need to recognize when a texting relationship is sinking. "I would say if they don't respond for a few days or don't respond at all, you have your answer that they aren't interested," matchmaker Susan Trombetti says. As hard as that might be to accept, it's best to move on when someone appears to show no interest. There's no harm checking in with your crush if you haven't heard from them in a day or two, but if you're always the one doing all the work, it might be a sign that you're more invested than they are. "If you notice that you're the one always starting the conversation, it might be a good idea to step back and see if they take the initiative to reach out," dating and relationship coach Nicole Haley says.

Online dating expert Carmelia Ray told Brides that boring responses from your crush like "yeah," "uh huh," and "k" are sure signs that the conversation is dying a slow, painful death. Pair that with no effort from their end to keep the text thread going, and you'll know it's time to let them go. There are plenty of fish in the sea, and you shouldn't be wasting your time with someone who can't appreciate your awesomeness.