What’s the best way to reply to this first message?

You get a message on a dating app and you’re thinking “What’s the best way to reply to this first message?”. Whether it’s the substance of the message itself, a lack thereof, or you’re just bad at the whole messaging on dating apps thing, trust me, I get it. The whole process can feel a bit unnatural, even for online dating veterans.

I’ve sent a lot of first messages in my lifetime. I’ve responded to a few as well. I’m not an expert, but I’m experienced. Hell, I think I’m pretty successful at online dating and as John C. Maxwell said “…a wise person learns from his mistakes. A wiser one learns from others’ mistakes. But the wisest person of all learns from others’ successes.”

So, let’s learn from my mistakes, but mostly my successes. Let’s propose some messages and message types that you’re likely to get, and the best way to reply. Plus, some Pro Tips for folks who send these sort of messages, so you can send better messages.

The Hey, Hi, Hello

Look, you either think these messages are lazy and aren’t worth a response, or you’re willing to give people a shot. Personally, I’ve always gone back and forth on whether or not to respond to a Hey message. On the one hand, rewarding someone for a lack of effort seems like a bad thing to do because it reinforces bad behavior. On the other hand, I recognize that sending first messages is difficult. Especially for people who aren’t used to sending first messages.

That said, you either don’t respond, or you respond and add substance for them to respond to. If you decide to respond, don’t just say “Hey” right back. Two wrongs don’t make a right. Reply by asking them a question either about the substance of their profile, or ask an ice breaker question.

Pro Tip: if you’re guilty of sending Hey messages you can add, at least, two sentences to the message and it’ll be 500% better. “Hey, I’m bad at sending first messages but wanted to do more than just say Hey. How’s your week going?” is better than just Hey. Not much, but it’s a start.

The copy/paste

Don’t respond. At all. It’s not worth it. I can forgive a short message but not a copy paste one. A message that is just a greeting shows you one of three things: Best case scenario they’re either clueless about what to say, or clueless about what makes for a good first message. Worst case scenario, they’re lazy. A copy/paste message betrays a sort of cynicism about online dating that I’m just not a fan of.

This person views online dating as a numbers game, a system that you can manipulate by messaging the most amount of people in the shortest amount of time with the same generic message for optimal results. This person is cunning, and manipulative, and would rather be disingenuous and look like they tried, rather than just trying and being mediocre at messaging.

Pro Tip: Don’t do this. If you’re worried about having to send a lot of messages because you think that a high volume is the only strategy that seems possible, stick to a basic message framework and customize it:

  1. Introduction
  2. Mention something about their profile
  3. Ask a question that requires more than just a one to four word response.

I used that same format for over more than a decade of messages, and it worked wonders AND took minimal effort.

The “I think we’d be a good match”

This is one of those sort of messages where you either ignore it completely, or just assume they have the best intentions, but are misguided and a bit naive about what makes for a good first message, so you reply and hope for the best.

Pro Tip: If you’re wondering “what’s wrong with saying that you’d be a good fit or a good match with someone?”, here’s what’s wrong with it and why it’s a waste of time. It’s safe to assume that the people you message (especially if you mutually matched) already think that you feel this way. It’s sort of like applying for a job and putting the line “I am applying for this job because I think I’m a good fit for it” in your cover letter. It’s implied already just by sending your first message.

Regardless, here’s how you respond to this sort of message. Ignore the part of the message where they tell you that they think you’re a good fit, and steer the conversation toward something substantive. If they really do think that they’d be a good fit for you, ask them questions that will help you decide if that’s true but don’t phrase them in a way that demands proving. “Are you a cat person or a dog person?” instead of “If you think we’re a good fit, are you a cat person or a dog person?”

The invitation to meet immediately

I am all for spontaneity, and seizing the moment. The moment you want, when you want it. So if someone suggest meeting up in their first message, and that’s what you want, get started on date planning. But also, do at least some preliminary screening to make sure you’re not about to make a huge mistake. Pro Tip: even if you’re meeting someone purely for a casual hookup, always meet in public first, and get the address of where you’re going.

If you aren’t looking to meet up immediately, I would suggest just declining. Based on their response to your declining their suggestion, you’ll get a good idea whether you’re a good fit. In my experience people who quickly suggest meeting are looking for sex, like 75% of the time. That other 25% are just people crunched for time. If they reply with something like saying that they’d still like to message and see where things go, keep on messaging. If they press the issue, ignore them.

Pro Tip: If all you’re looking for is casual hookups, there’s nothing wrong with leading with that, but at the very least you should save that for after the first message. Maybe this person just plain sucks and you wont want to be around them. Clear that up first.

The message based on your photos

If the message is about what’s in your photos, i.e. asking you about something in your pictures, respond to their message in the same way (i.e. Where are you in your 4th photo, is that Machu Picchu?). If the message is them just objectifying you, feel free to not respond at all. Unless that’s all you’re looking for. In which case, respond in kind. I’m all for telling someone they look good, but if someone leads with that and only that, odds are good that they’re not looking for anything beyond the physical.

The general compliment/praise

“Thanks”, and ask them a question that requires a substantive answer, if you feel like this sort of message is worth responding to.

Pro Tip: A compliment is a great way to ingratiate yourself toward someone, but a compliment alone just wont do it. Compliment, then add substance to your message.

The “You’re so amazing! Why would someone like you be on this app?”

Pro Tipthis is a terrible idea. Stop doing this, like, yesterday. Whatever you think you’re accomplishing by sending this sort of message, trust me when I tell you that it wont work. It’s not flattering, or funny, or clever, or original.

If you do decide to reply to this message, I’d recommend being short with your answer and changing the subject. “I wanted to see what was out there. How’s your week going?” should work just fine. I think when most people send this sort of message, they’re not trying to imply that some people are beneath or above online dating, they’re trying to convey the same feeling that  “what’s a nice person like you doing in a place like this?” might convey. Flirty, humorous, complimenting you while being self-deprecating. It doesn’t but not everyone reads my blog. ¯\_(ツ)_/¯

If they continue down the “lol, BUT WHY would someone like YOU need to be on THIS SITE though, I just don’t get it”, feel free to stop responding at that point. They’re not likely to let the “BUT YOU’RE SO AMAZING AND ONLINE DATERS ARE GARBAGE” bit go anytime soon.

The trolling/insulting message

If you are going to respond, Roast them. FLAME THEM. DRAG THEM. Treat them as mercilessly as possible. Then screenshot it and post it on social media. Let us all share in the well deserved roasting.

Or, and this is way more inline with what I would do, ignore them, report them, and block them. Some people go out of their way to be the most worst person possible to get a rise out of people, because it makes them feel good. It’s safe to assume that anyone who messages you to insult you or troll you is looking for that reaction, because it nourishes them. I think that not giving someone who is garbage what they want is its own reward. Take it one step further and block them. If they’ve said something that might violate the app/site terms of service, report them then block them.

The message based on the substance of your profile

The Holy Grail of messages. What pretty much every person who is using online dating to find a genuine connection is looking for when they’re dating online.

How to respond is simple. Reply to their question or comment, and ask them a question about themselves, or about the substance of their profile. Repeat until you decide to stop messaging or meet. Give me a shout out when this approach works. 😉

In all seriousness, the goal for any of your responses to a message on a dating app should be the same. Make them substantive so they can lead toward either meeting, or coming to the conclusion that you’re not a good fit. Build a connection, or filter someone out. It’s not rocket science.

Good Luck Out There.

Also published on Medium.