Learning how to present yourself online is a lot different than presenting yourself in person. When you’re face-to-face with someone, you have to worry about body language, smell, touch, and other nonverbal signals.
On a dating site like Match, it’s just per words, and what you say is what defines you. No pressure!
When you communicate in words, it can be hard for your personality to shine enough to cut through the noise. I’m sure you’ve all read the stats that hot girls can get hundreds of unsolicited messages a day on the apps.
The good news is that it isn’t really that hard to stand out, once you learn the ropes. And when you can set yourself apart from all the other messages, you’ve got a chance for her to become intrigued with you and want to find out more.
So let’s go through a little step-by-step messaging playbook for guys on Match (and any other serious dating sites) to up your chances of finding the love of your life! (BTW, I found my wife online.)
Step 1. Prepare Before You Start Messaging
Okay, so if you join the app and just straight off start messaging people, you’re not going to have a great time. You need to prepare before ever sending that opening line.
Add 5 Strong Photos
You’re trying to bring attention to you and your Match profile, so you’d best be trying to get the most bang out of your buck. If they check you out and are unimpressed, chances are, they’re not going to send a like, and that’s the only way to unlock a conversation on Match.
Your profile must be on point. Make sure you’ve got everything filled out as much as possible.
Get five photos up there (don’t do the one with a fish, it’s overdone). Choose pics that show you and what you like doing.
Fill out all of the fields and complete as much as you can. This shows that you are serious about finding whatever it is that you are looking for.
Figure Out What You’re Looking For
Are you looking for a sexual partner? A situationship? A hookup? A long-term relationship? Any of these things is fine, but the more you know what you’re looking for, the more you can tailor your profile to attract the ones that you want.
My Insight: If you’re on Match, you should know that more users are going to be wanting a relationship or marriage. Members also tend to be over 30.
If you are a young 20s dude, just looking for some fun, Match may not be the right dating pool. If you’re in your 40s and looking to settle down, you should do all right as long as you convey the vibe that you are going for.
Know Why You’re Messaging Her
Yeah, I know, it’s ‘cause she’s hot, but it’s got to be more than that to earn a great one. To quote Silent Bob in Clerks, “You know, there’s a million fine-looking women in the world, dude. But they don’t all bring you lasagna at work. Most of ’em just cheat on you.”
Her looks will cause you to stop on her profile in the Discover section. But what is in it that you think might make you guys a good match?
- Do you have the same hobby?
- You used to live near each other?
- You’ve both visited the same place?
You need to identify something intriguing before you message her. Luckily, Match profiles have a ton of details about interests, values, and lifestyle, so there should be plenty for you to discover.
Step 2: Send the First Message
Match only allows communication between mutual matches. So if you’re able to send a message to her, that means she’s sent a like to your profile first. You’re already in her good books. Now you just have to stay there.
You can never get a first impression back. So let’s try to put our best foot forward and make an impact! Basically, you want to show up, make her smile, suggest why you might be a good match, and then leave her with an easy call-to-action.
It has to be more than, “Hey. You’re cute. Want to meet up?” Here are a few ways to strike up a conversation:
| Common Experiences | “I see you love to ski also. What’s your favorite trail?” |
| Funny Observation | “Did you mean to wear sneakers at the beach? Not a fan of sand on your feet?” |
| Compliment | “That’s a pretty sweet hat! Where did you get it?” |
| Opinion | “Okay, I can see you’ve been to both Spain and France. I think France has the better food, what do you think?” |
| Situational | “That was a crazy storm last night! I hope you stayed dry?” |
If you want to show you’re more serious and intentional, write something a little longer and include a personal detail. Something like this:
“That picture of you skiing is beautiful! My favorite place to go skiing is in Vermont, though I’ve busted my a** in the Alps attempting to snowboard. Where’s your favorite place to go?”
The first message doesn’t need to be deep. It just needs to be friendly and interesting enough to spark a response.
Keep Messaging: The Back & Forth Matters
Yeah, you got a message back! Congrats, huzzah, and all that jazz …now what? You’ve set the hook and gotten her a little interested. Time to capitalize on it.
Hopefully she will have responded with something that you can comment on and ask another open-ended question.
At first, the questions and answers should be easy. Think of a lob in tennis. You want to make it really easy to bounce it back in your direction at first.
As the messages continue, you can get a little more in-depth and have longer messages (still talking 5-6 sentences max).
When you can, you want to leave with a question, hopefully somewhat open-ended, to allow her to expand her answers.
Pro Tip: Match has a “Your Turn” tag on chats to remind you that it’s your turn to respond. Don’t leave someone on “Your Turn” for longer than a day if you want the chat to keep flowing.
Learn to Share
Not everyone will know the right questions to ask to elicit the best and most interesting answers. While you are trying to check her out and see if she has value, you also want to make sure you are demonstrating value.
If we are still using that skiing profile from before, you could say something like:
“Oh wow, that’s cool, I’ve never been to Okemo. The closest I’ve come is Killington, but after my surgery, I’m not going there again!”
Immediately, she’s going to want to hear the story of how you wiped out, broke your arm, and had to get transported down the mountain.
Another way of doing this is leaving what I call question bait.
For example, if she asks you, “Do you like to cook?” And you say something like:
“Not much, just a little bit. And I’m still not allowed to enter my grandma’s kitchen after the Thai noodle incident of 2017.”
What does she want to know about now? The noodle incident! And you directed the conversation there, so you can share a fun story.
Step 3: Ask Her on a First Date
Things are going well, the convo is flowing. Now how do you turn it into an actual date? Think of something that she said in an earlier conversation or on her Match profile. Does she like a certain type of music or food? What makes her happy?
If you can ask her out by referencing something you’ve already discussed, you’re in the green!
Example: “Hey, I remember you saying you like carrot cake. There’s a cool bakery downtown I’ve been meaning to try. Want to check it out this weekend?”
If asking her specifically gives you the shiver willies, you can also tell her where you are going to be, living your best life, if she wants to join you.
Example: “There’s a cool street festival downtown tomorrow night that I’m going to. Would be great to see you there if you wanted to meet up!”
Step 4: Follow the Dos and Don’ts of Messaging
Everyone walks their own path in dating. There is no one-size-fits-all approach. But I’ve coached many singles and helped them shoot their shot, so I do have some idea of what generally works and what generally does not work.
If you’re on Match, that means you’re a bit more serious than the lot, and you want a relationship. So you’d better go about it the right way.
Here are my Do’s and Don’ts for messaging:
Messaging Dos:
- Comment on something she talked about to show you listened
- Show interest in any hobby or goals they have.
- Try to use natural humor, not stock jokes
- Match their message length and emoji/meme use
- Don’t be afraid to tell the truth if you’re nervous. It makes you human.
- Do use as correct grammar as possible
- Try and get off the app as soon as possible
- Use their name or username. People like hearing their name.
Messaging Don’ts:
- Don’t dominate the conversation, use lots of questions
- Don’t apologize when not needed (“Sorry for bugging you, but…?)
- Don’t fire off questions like it’s an interrogation.
- Don’t fake interest in something you know nothing about. Instead, “that’s cool, why do you like it.”
- Don’t compliment their body or physicality. It gets old. Compliment something else.
- Don’t share too much, too soon. People enjoy some mystery.
- Don’t stalk their social media before meeting them
- Don’t wait days between messages.
Granted, everyone is going to be a little bit different, and you’ll certainly have to adjust as you go. But if you start with these and go from there, you’re going to be ahead of a lot of the guys out there!
