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5 Ways to Up Your Message Game and Improve Your Online Dating Success

Feeling tired of messaging on dating apps and getting nowhere? I have a simple answer: stop. No, don’t stop messaging. Rather, start making the most of your messages. 

Messaging, no matter how much we loathe it and how it can make the early stages of dating feel tedious, boring, and frustrating, is necessary. That’s because online dating is ubiquitous. So, too, are the messaging platforms they have built into them.  

Even if you hire a matchmaker/dating coach to strategize with you, online dating is still the most effective way to access singles. The idea is to narrow your search from there. How you interact when messaging is one way to judge and be judged by your single peers. 

So, if your messaging skills need some improvement, listen up. I’ve got five easy steps that can take you from digits to date.  

1. Don’t give out your phone number in the first message. 

If someone wrote to you, “Hey, here’s my phone number. Feel free to text or call me,” what would you think? Probably that (1) this person is way too aggressive, (2) they’re desperate, and (3) they’re likely sending this message to a lot of people, not just you. Feeling special yet? 

Probably not. Well, that’s more reason not to send this kind of message to others. The idea is to engage someone you’re interested in with a message, not chase them away with one. 

2. Personalize your messages.  

So how do you engage? For starters, personalize your messages. If you’ve seen someone’s profile on a dating app, reference a detail you read about them from it. The message doesn’t have to be long. In fact, it’s better if it’s short. Ask a question to get the conversation going. 

Think about your first exchange as building blocks. If you were building a foundation for a building, you wouldn’t throw a bunch of cement blocks in a pile, would you? The same goes for messaging. Think slow and steady. After all, you want to build rapport between you.  

3. Pay attention to the rhythm of your exchange. 

During each exchange (there could be a few messaging “sessions” before you take your interactions to the next level with a phone call), pay attention to the rhythm of your messaging. What does this mean? If you send one message, wait for a response. When the person you’re messaging sends back one, two, maybe even three short messages, then respond.  

Don’t write volumes. Balance the length of your messages with those from the person you’re messaging. And, heaven forbid, if the person you’re messaging drops off or doesn’t message you back right away (or ever again), don’t blow up their phone with “Hello?” or “Did your cat get run over?” or “I guess it’s over.” 

I shouldn’t have to explain how you sound. Okay, since you asked, I will: #psycho  

4. Offer to chat. 

Messaging can be fun and a total rush as you see the name of the person you’re interested in pop up on your home screen again and again. But it can also get old fast, especially if you’re messaging someone on the other end who’s on the dating site because they’re serious about meeting potential matches, not finding other messaging buddies.  

So, if after a few exchanges, you’re interested in talking on the phone, offer to chat. If the other person dodges you and continues to strike up conversations over the dating app, ask a second time politely. Don’t wait too long to make this second request. Your time is valuable.  

If they still don’t take you up on your offer to speak the next time you ask, take that as your cue to move on. Then do so without drama. 

On the other hand, if the other person says they’d like to talk, pat yourself on the back because it means you’re doing this messaging thing right. And you’re also ready for the next step, which is to . . .    

5. Exchange phone numbers and schedule a convenient time to talk. 

Convenient should be the operative word here—for both of you. You want to talk when you have each other’s attention.  

So pick a time when you’ll be at your best. When your boss isn’t within earshot, you’re in aisle ten at the grocery store, or you just had a fight with your ex or teenage son. 

Blow it, this call could become your first and last call with them. Better yet, it could be the call that leads up to your last first date.