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Up Your Dating Game with Better First Messages

By on Feb 24, 2018

There’s a real issue with online dating: How do you reach out to someone with something meaningful before you know if they will even respond?

This is a big problem, especially for men who are still supposed to make the first move. But as the online dating platform Bumble has shown, it isn’t a gender issue—when women are in the position to make the first contact, they also struggle with this issue.

The problem is that you don’t know if the other person will respond, so you don’t invest much in that first message.

This makes a lot of sense on the surface, especially for guys who might be in fierce competition for a woman’s attention. If every first message requires a lot of time and effort, and the response rate is low, who has time for longer messages? Who has time for crafting thoughtful messages to hundreds of people who might not even respond?

So, as a result, many people who make the first move online do something quite reasonable: They send something short. Maybe something really short, like “Hey.” This doesn’t take a lot of time, and it signals interest as the thinking goes.

Go Deeper with that First Message

The problem is that “hey” doesn’t work very well. It says nothing about you, it says nothing about why you and this other person should be talking. If anything, it shows that the other person should not respond; you didn’t take the time to even try writing a good first message. You’re phoning it in, so you’ll only get a response if your profile photo is really good and the other person is talking to you based on looks.

“Hey” and other throwaway first messages just aren’t the way to go. You gotta go deeper.

This doesn’t mean you must spend 45 minutes on every first message. That would be awesome but also perhaps time-management suicide. What you should instead do is actually read the person’s profile and come up with a quick first response that is actually meaningful, even if it is short. You need to spend more time than cut-paste or a generic line, even if you probably can’t invest lots of time on that first message.

Elements of a Good First Message

The point of that first message is getting to the second message. How do you do that? You get them dreaming, and you invite them to start creating that dream one step at a time.

Everyone who is dating online has a goal. For most, it is finding a fulfilling romantic relationship. For some it is having sexual intimacy. Occasionally there is another reason like having more friends. But whatever the reason, there is a goal. Your job is signaling that talking with you might help them reach that goal.

So your job is teasing them with value. You in that first message are suggesting that you might help them deliver on that goal—and get them dreaming about it. Are you the love of their life? Could you be the one they have been looking for? Nobody knows, but based on your first message you can have them dreaming and wondering if you are that person; you are hinting at what they really want.

The other person can only know for certain, though, if they write back. If you get that action from them, you’ve reached the goal of your first message.

So in a first message to someone, you want to show value by relating how something in their profile relates to you in a good way. If they’re looking for someone who is good at listening, talk about being a good listener. If they like to go out on the town and have fun on a Friday night, talk about how you try new restaurants every weekend and would love to have them join you. That sorta stuff. Nothing long. Nothing that takes a load of time. But something that speaks to their profile—and shows how you fit with them and their interests.

Once you establish that, you set the scene for the second message by asking an open-ended question.

Open-Ended Questions Make the Difference

The second part of a good first message is equally if not more important. You must get them talking and sharing with you. Chances are good that they will respond if you’ve shown value, but then you have to do the process all over again with the second message—and you’ll run out of stuff to talk about pretty fast if they don’t give you something more to work with by talking with you in a meaningful way.

More importantly, without them responding with something meaty or meaningful, you have no real conversation. This isn’t moving toward partnership, and you’ll go nowhere fast if you don’t light that fire of partnership together.

So beyond relating to them and showing value by referencing their profile, you need to ask an open-ended question that advances the conversation and gets them responding in a meaningful way.

As dating Greg Schwartz mentioned in our recent video, Upping Your Online Dating Game, questions such as “do you like movies?” does little to advance the conversation. Questions like that invite one-word responses like “yes” or at most a tepid response. They don’t give you anything meaningful you can share.

Better questions are open-ended questions that dive into what might actually matters to you and the other person. You’re asking the other person to talk on a topic they care about—and you are tempting them by leaving the space for a meaty response if they are ready for it.

You don’t yet know the other person, so we’re not talking about really deep questions at this point. That will come later. But you also don’t want to stunt the conversation by asking throwaway or closed questions.

So if the person you are writing is showing a photo of them on a beach in the tropics, for instance, you could ask if they travel a lot and where they like to go. You also might inject a little bit of yourself and a hint at the response you’d like by telling them that you like to hang out in Cancun every year because work can get pretty crazy, but you’re thinking of going elsewhere because the party scene has gotten out of control there recently.

This type of response opens the door to them telling you about their life, and talking about a trip they might have enjoyed. It shows that you also like to travel, and you take care of yourself. It hints that you could be a good person to go beach-hopping with at some unspecified future date, and it opens the door to a conversation about what kind of vacations you and the other person enjoy. It hints that you might have an important job, but that you take care of yourself despite the demands on your time. A short message like that also does other things subtly (did you spot any?)

Another example is if you see someone’s profile and they are into the TV show, Game of Thrones. You might ask them if they’ve seen the latest episode, and where they think the show will go next. Maybe you will also add in that you host Game of Thrones viewing parties from time to time.

This response gets the other person talking about a show they really care about, and engages their imagination and the positive memories about the experience of watching the show. It shows you are interested in what they like, and that you care enough to ask their thoughts about the direction of the series. It implies you are a serious fan, too, and that the two of you could have fun engaging around the show and more. It shows you can be fun and creative. It invites other questions, too, and tempts the person to respond.

You can get a lot out of a quick message and an open-ended question!

Next Stop: Dating Adventure

These are the sort of first messages that get responses and lead to dates. They don’t work all the time, and there will be missed opportunities and people who don’t respond. That’s part of the process, though; people are not simple creatures, and so neither is dating them.

But if you put these simple tips into practice when writing those first messages, you’ll have a much better success rate and get the results you want from online dating faster.

And if you don’t? Call me.

Dating can feel frustrating or overwhelming, but it actually is not hard. You just have to know what really matters, and make sure you’re taking the action around what matters. Where most of us get stuck is not taking the right action, or getting lost in all the tips and advice. So having the help of a coach can make a big difference; we can help you zero in on what’s not working and why, and then get you making the adjustments that lead to the dating success you want.

So if you are finding yourself stuck, reach out!

P.S. If any of this resonates with you, next week we’re hosting a Q&A with dating coach, Greg Schwartz. Come join us! We’ll be talking about this and other topics around online dating.


Peter is founder of Kowalke Coaching. He also is founding director of the Philia Mission, a small charitable organization. Contact Peter.