Online Messaging in Dating: A Complete Guide

My parents are in their 50s, so over Thanksgiving, Christmas, and family trips I spend plenty of time watching a happily married couple stroll ahead of me holding hands. And I keep thinking they don’t realize how lucky they are.

Sure, they’re lucky to have found each other, and lucky to fall deeper in love every day, but they’re also lucky they never had to date in the age of online messaging.

Online messaging is the practice of sending written texts via an online platform.

Imagine never knowing the dread of waiting on a reply after spotting that the person was just online on Instagram. Think of all the headspace you’d free up if you weren’t decoding why someone sent two emojis last time instead of their usual three. As Kanye West famously (or infamously) put it: “I guess we’ll never know.”

In the end, daydreaming about old-fashioned courting gets you nowhere. The internet is here to stay for the foreseeable future. From texting to sliding into DMs to shooting your shot with a match on a dating app, messaging online has turned into a basic part of every modern relationship.

This complete guide gives you every tip and tool you need to handle it well. I’ll cover the different kinds of messaging, the key elements of a better messaging approach, common challenges, and more. Let’s dive in.

Kinds of Messaging

One text can pave the way to a deeper, more meaningful bond, or it can bury a “coulda-been” relationship in a digital grave. That’s why it pays to learn what people jokingly call the “rules and regulations” that govern this modern tech.

Messaging comes in lots of forms, and each brings its own flavor to today’s dating dynamics. Between good old texting, social media DMs, and dating app message threads, you have plenty of communication channels to pick from, never mind figure out.

Text Messaging

A bit of background: I was 10 when my first cell phone arrived. Nobody else in my grade had one yet, and its monthly text cap would send me into a spiral today.

These days, if you met someone older than 8 who didn’t have a cell phone, you’d likely wonder whether they belonged to some religious cult. That’s life in The Digital Age.

Now that practically our whole species has plugged in, dating has gained some clear benefits and some clear drawbacks. The most obvious plus is convenience. A few taps on your screen let you say “Good morning!” to your boo (or future boo), trade House of the Dragon memes that make you laugh, or talk over plans for a dinner date later in the week.

The flip side is that texts are extremely easy to misread. More on that in a bit.

Instant Messaging Apps

Honestly, regular texting (the kind that runs through your phone’s data network) isn’t very different from messaging on a platform like WhatsApp, Messenger, or Telegram. Either way, two or more people are trading digital messages in a matter of seconds.

Both usually let you send messages in several formats too, from typed text with emojis to voice memos and even video calls. (If you’re like me and love a long yap session, those last two are non-negotiable.)

Social Media Messaging

During the “shooting your shot” and “just starting to cook” phases of dating, much of your messaging may happen on social media platforms like Instagram, Facebook, and Twitter (now called “X”).

Besides displaying a carefully curated gallery of your stunning, lavish, fun-packed life, these social apps let you message followers and strangers alike. Sliding into someone’s DMs (in other words, sending a first message to a cutie you spot online) is now a common way to flirt, and it can lead to new relationships.

Dating Apps Messaging

If things aren’t going down in the DMs, they may well be going down in dating app message threads (which, admittedly, sounds less cool). Popular dating apps like Tinder, Bumble, and OkCupid all have messaging tools for sending flirty notes to your matches, though whether every messaging feature is free varies by app.

On a free Tinder account, for instance, two singles can message each other once they’ve matched. To reach out to a hottie before matching, though, you’ll have to upgrade to Tinder Platinum or Tinder Gold.

Group Messages

Ah, the group text. Some people love it, and others want to hurl their phones at the nearest brick wall. This kind of communication, where three or more people share one message thread, is hugely entertaining at its best and mind-numbing at its worst. And that’s before romance enters the picture.

Should your new partner add you to a GC (or “group chat”) that includes their family or friends, you may face a whole new rulebook. In a family GC, you’ll probably want to sound more polished and “business professional” and less casual, at least early on.

Your partner’s friend GC may be more of an anything-goes zone, overflowing with drama inside the group, wildly inappropriate memes, and running jokes nobody else gets.

Whichever it is, watch how everyone acts so you can learn the norms and respond to match.

4 Key Elements of Good Messaging

Sending a text only takes a few finger taps, but it still deserves real thought and care. A texting exchange has many parts worth considering, particularly if you plan to use your digital conversations to help your romance grow (and, let’s face it, you will).

1. Tone and Style

A Key & Peele sketch captures this exact struggle of reading the tone of a text.

Getting your real meaning across in a text is extremely hard. Something you intend as playful and flirty might strike someone else as rude or even offensive, so be extra careful as you type out your message.

2. Timing and Frequency

How quickly you reply to texts or online messages also matters a lot when you’re dating. People may read your response time as a sign of how interested you are (or aren’t).

If I wait a whole day to answer a potential partner, for example, either I’m not into it or I’ve come down with some sudden, deadly illness. There’s truly no middle ground.

Not everyone texts the way I do, of course, but as a rule of thumb, a reply within a few hours works best if you want a healthy relationship, unless you’ve said you’d rather talk by phone or FaceTime.

3. Conversation Starters

How you open a conversation will probably shift with the person and with how far along your relationship is. With more intimacy, couples usually lean on shorthand and feel free to be totally goofy. The early days of courtship, though, tend to be more reserved.

At first, you’re still learning about each other and testing whether your vibes line up, so expect to rely a lot on icebreakers and compliments.

Once the flames of romance start building, questions like “Who’s your favorite Harry Potter character?” and “Do you have any pets?” give way to weightier ones such as “What’s your love language?” and “Do you want kids someday?”

As your bond deepens, you may have to be more careful about how you word messages so they land the way you mean them.

4. Visual Elements

Thankfully, texting tools have grown along with technology. Emojis, gifs, and memes now help us say what words can’t quite capture, which goes a long way against the texting mix-ups mentioned above.

We can also send our crushes photos and videos (of the cafe we’re sitting in, the dog asleep on the couch, or something a bit less PG), which can help build intimacy and connection.

Common Pitfalls

Every technological leap has its downsides; life always balances yin with yang. Chief among them are miscommunication, ghosting, and getting trapped in pen pal purgatory.

Misinterpretation and Miscommunication

With no tone of voice or body language to read, messages frequently get interpreted in ways the sender never meant. That can create plenty of stress or friction between any two people, let alone two people caught up in a charged romantic situation.

That’s why emojis, memes, and gifs can be especially useful for getting your point across. The wink emoji signals playfulness, the heart emoji signals care, and, well, everybody knows what the eggplant stands for.

Remember: when a message you receive is unclear, you can always just ask the sender what they meant.

Ghosting

If nobody has ever ghosted you, either you’re new to dating apps or you’re the ghost (shame on you!) leaving people in limbo. Ghosting, which means suddenly dropping all contact without a word of explanation, is hitting modern daters at a worrying rate, and it will probably keep spreading as technology feeds people’s urge to hide behind their screens.

Since it happens suddenly and for no apparent reason, ghosting often leaves the other person deeply confused, hurt, and betrayed. So here’s my parting advice on it: That conversation you’ve been dodging may be hard, but have it anyway.

Pen Pal Purgatory

It’s been a month since you connected with someone online, and the two of you still haven’t met in person? Then you’ve probably landed in Pen Pal Purgatory. It’s a tricky spot to be stuck in: the longer you hold off on booking that first date, the tougher it becomes to make the leap from screen to real life.

And if you’ve tried to make plans and they’ve sidestepped every one, you can reasonably assume they have a reason for not meeting you. Maybe they’re stringing you along, maybe they’re lying about who they are, or maybe they’re a pop star on tour (which would make a steady relationship a bit of a challenge).

To stay out of pen pal purgatory, make it clear early that you want to meet. If they don’t match your effort, spare yourself the wasted time (and possible heartache) and move on.

Best Practices

We’ve got places to be and people to see, and we (most likely) want our new relationships to grow in healthy ways too. That means getting the most out of our texting by following some best practices, a handful of which are covered below.

1. Build Rapport With Friendly Questions

Just as on in-person dates, the aim is to learn about each other and find out whether you’re a good fit.

If you’re unsure what to ask, choose questions that can’t be answered in one word, or with a “yes” or “no” — like these:

• What experience from the past year meant the most to you?
• Which qualities matter most to you in a relationship?

Try asking warm, engaging, thoughtful questions that push both your chats and your budding relationship forward.

2. Respect Boundaries

Every successful relationship depends on respecting boundaries. You’ll probably learn exactly where someone’s boundaries lie as you get to know them, but in general, don’t blow up their phone, pass their personal details along to others, or fire off a “u up?” text at 2am.

3. Be Authentic

Screens give your conversations a layer of anonymity, so you might be tempted to show the person you’re pursuing some other version of yourself. I strongly recommend against it, because the truth always surfaces eventually, whether that’s today or three months down the line.

Rather than putting on digital airs with excessive politeness or burying your texting partner in over-the-top flattery, just talk to them as the real, authentic you.

Quick, Easy Communication

You only need decent eyesight and a quick glance around to notice how thoroughly digital messaging has become part of modern social life.

Unless you’re in the same boat as my mom and stepdad (lucky enough to have met before this huge shift), there’s no avoiding messaging when you date. Knowing the rules of online communication will be key to making your relationships work, especially the romantic ones.

Don’t worry, though. Follow the best practices above, type with purpose, and online messaging can be more friend than foe. It might even be what keeps your loving relationship glued together. So stop resisting. Hang in there, lean in, and start studying up on those emojis.