Could you give me some advice on how to talk to guys online?


Rhodiola_Rosea asks:

Hi y’all ūüôā sooo I just started using this dating app but I realized that I have pretty much zero experience talking to guys online ūüė¶ It’s a bit strange because I can speak to them just fine face to face).

Could you give me some tips?

Demetrius says:

It might be easy to say “The same way you would talk to them face to face” but I don’t think that’s necessarily true. Let’s say you’re somewhere public, like a bar, or a party, and you’re meeting someone new. What’s the first thing you’d say? Probably a greeting like “hey” or “hello” and take it from there. Which is the biggest no-no when it comes to online dating. In online dating, your first message usually contains a hello, an introduction, and a question. In person, that would come off as a bit intense and would be broken up between 2-3 back and forth exchanges. Face to face, it’s actually a bit more difficult for someone to walk away compared to online, where you can just ignore a message or block the person. Online dating messaging is closer to text messaging than anything else.

One quick caveat, advice on how to talk to guys online is from a place where I’m giving advice based on how I would want to be communicated with online, and assuming that it mostly holds true for men in general. I have an extensive amount of personal experience with talking to women online, but no firsthand experience on how to woo a guy online.

With that out of the way, let’s get into some don’ts first. Mostly because lists are useful. So, some basic don’ts when messaging a guy online:


  • Send multiple 1-2 line messages when one paragraph message will suffice
  • Send one word messages
  • Expect them¬†to carry the entire conversation
  • Close a conversation topic without opening another
  • Message or respond to someone you’re not interested in

Sending multiple messages when one will do is something that a lot of people do online and it can get to be pretty annoying, especially if you have notifications on your phone turned on. If you feel tempted to send multiple messages, back to back, ask yourself if you could group all those little messages together. If everything you have to say is about one thing, group it together. If you’re asking about date planning, but also their recent trip abroad, that can be two separate messages.¬†The one word message thing will always be interpreted as a sign of disinterest, or a lack of effort. It is consistently, the worst thing you can do when sending dating app messages, and while men tend to be a bit more forgiving when it comes to¬†spelling or grammar issues in online dating, they’ll still judge you if you only say “Hey” to them. In fact, if you just said “Hey” followed by “Sorry, I’m not good at sending the first messages” you’d be doing yourself a huge favor. Adding literally anything more than just “Hey” or “Hey, how’s it going” will improve your odds of getting a response exponentially.

Once you get someone¬†engaged in a conversation, the best thing you can do is to help carry the conversation. Assuming you’re messaging straight guys, most of them are used to having to both open conversations and to drive and carry them forward. We get messaged less, even if we’re of comparable attractiveness, so most of the time we’re sending more messages, and you know what, that can get exhausting. Everyone gets exhausted by online dating in different ways and one of the ways straight guys get burned out on online dating is feeling like they’re doing the same thing over and over, sending hundreds of messages, and not seeing any real results. If you’re someone who not only helps move the conversation along, but also answers and asks questions,¬†you’ll be making messaging easier for both of you.

Finally, if you don’t like someone, don’t respond to their messages. You might feel the need to reply to the men out there who maybe aren’t your type, but seem nice enough, so you don’t want to make them feel bad by passively¬†rejecting them. Don’t do that. You’re wasting his time, and yours. If you’re not into them, either don’t reply, or tell them you’re not interested. Not so fun fact, if you do either of those, you might get a pretty hateful response in return. It’s one of the bad parts of online dating that we can’t really change, sadly, so I’m just warning you in advance. If you’re on a dating app where only your matches can message you, and you match with someone and know you don’t intend to ever respond to them, unmatch them ASAP.

I’ve written a ton of advice on the subject¬†of messaging, including opening messages and continuing conversations,¬†so I won’t rehash it all. With that said, here are some quick messaging Do’s:


  • Be concise in your messages
  • Ask, Answer, Repeat
  • Send a first message (if you want to)
  • Push the conversation where you want it to go

When I say concise, I don’t only mean to keep it brief. Your message should be comprehensive, but brief. Small talk is fine and all, but it should not make up the bulk of your conversation. You should limit your “how’s your day” messages and try to add more substance to the conversation. Keep it short, and simple, but make it substantive.

The key to keeping any conversation with a stranger going is to ask, answer, repeat. If a question is posed, answer it and ask a question (even the same question). If there is not a current conversation topic, ask a new question. Repeat this until you either meet this person, or decide you never want to meet.

While Bumble is popularizing the Sadie Hawkins model of messaging, it doesn’t mean that’s the only site or app where women can take the lead on sending the first message. See someone you want to message? Send them a message. For context, women on OkCupid are messaged 17 times as frequently as the men on the site, so if you’re a woman who sends the first message, you’ve got a distinct advantage over your peers. Fun fact, my ex actually sent the first message, not the other way around, so take from that what you will.

Finally, don’t be afraid to push the conversation. Many woman ask me the best method to get a man to ask them on a date and my answer is usually some variation of “Why don’t you just ask him on a date?”. I understand that we’re in a sort of in-between space where most women are very independent and modern, but also want to be treated chivalrously, but if you really want to go on a date, push the conversation that way. You don’t have to explicitly say “TAKE ME ON A DATE YOU BIG LUG!” but asking “So, when are you going to take me out?” works well. It’s okay to be a bit aggressive from time to time, because fortune favors the bold.

Trust me, it’s easier than it seems to message anyone on online dating. The usual caveat applies though. Even the best message, crafted using messaging best practices, sent to someone who seems perfect for you, can go on unanswered. Don’t let it discourage you.

Good Luck Out There.

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