How to Start a Conversation With a Woman Online: What Really Works

We give you the best ways to start a conversation online so you can turn on your mojo and land a date.
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Online dating is a great way to get out there and meet women, especially once you get comfortable holding a text conversation. In this guide, I’m going to walk you through how to start a conversation with a woman online and how to keep that conversation going.

It is somewhat of an art form but it’s much easier to learn than you think. No matter who you are or what your personality may be, at least some of these tips will apply to you. By the end, you’ll have some actionable steps that you can implement to see improvement today.

How to Start a Conversation with a Woman Online

One of the biggest mistakes guys make when learning how to start a conversation with a girl online is writing something bland and uninspiring. You've gone out of your way to find the right dating site (if you’re still looking, we have a few recommendations for the best sites to meet attractive older women) and find a woman you're interested in, but then blow it by being boring on your first message.

Talk to any attractive woman and you can bet “boring” is one of the top reasons they’ll stop talking to a guy — don’t let yourself be one of them!

For example, you wouldn’t believe how many messages beautiful women get with something like “Hey” or “What’s up?” or even “Hello gorgeous!” and nothing else. They promptly ignore these lame messages and pay no further attention to guys who write that.

If you really want to improve your chances and truly figure out how to start a conversation with a woman online, you have to put in a little more effort from the start. It all begins with the first message to grab attention and interest. (Of course, you should also make an eye-catching profile with a superb picture to improve the amount of interest you get as well).

Finally, you should use smileys, emoticons, gifs and other similar things when talking to women on Facebook or any other online platform. It’s incredibly difficult to display emotions and feelings through text, so use these things to your advantage. Because you want to come off as playful and not like you take everything too seriously. If you're talking on Facebook, another way to show that you're a fun guy is through your profile.

We have some great tips below but if you are looking for a more complete guide to improving your chances with older women there are a few great books out there that are worth picking up. Here are some of the best ways to start a conversation online that work:

Start a conversation with a woman online by being provocative

This is one of my favorite ways to start a conversation with a woman online because it gets me a ton of replies. You simply write a provocative sentence as your first DM to a woman. This sparks interest and creates some anticipation.

For example, one of my favorites is:

“Hi. You know, from looking at your pictures, I can’t decide if you’d be the nicest girl on my naughty list or the naughtiest girl on my nice list.”

When you write the first message like that, assuming that your profile is in great shape, most women will reply back. Make sure to tease them playfully and in a lighthearted way on their replies and continue the conversation from there.

Many women will even ask you the same thing to see if you’re a “nice” or a “naughty” guy. Create a little mystery and anticipation by saying something like “Oh, if you’re lucky, you may find out a little later on . . .”

The fact that a provocative message gives tons of opportunities for fun and playful banter is why it’s one of the best ways to start a conversation online.

Just make sure you know the difference between provocative and sleazy. A playful message like my example above works well. Starting with “hey babe, want to see my 🍆?” isn’t provocative; it’s weird, creepy and unwanted.

Witty openers are perfect for starting a conversation with a woman online

Another awesome way to start conversations online that gets a lot of replies is to write a witty first message. That said, it may not necessarily be the easiest way because it does actually require a sharp wit and a great eye for details.

I’m not going to give you any specific example here because what you write will mostly depend on what you notice about the woman in her profile. Also, on your sense of humor and wit, which are entirely subjective and personal.

However, it’s safe to say that if your first message is something that’s witty and interesting, it will definitely grab attention and get you a lot of replies, which might also get women to like you online. Just remember not to go overboard with a message like this and make sure that it’s lighthearted.

Women like men who are witty, there’s no denying that. Because guys who are witty around women are rarely desperate and needy. And women love going on dates with witty guys.

Humour is something everyone finds attractive

One of the best ways to start a conversation with a girl online is by writing a funny first message that will get a laugh. This works especially well if you're messaging women on Snapchat. That’s because it’s pretty much one of the best first impressions that you can make! It shows that you have an amazing sense of humor and are most likely fun to hang around with.

It’s incredibly easy to transition from a funny first message that got a great response to a normal conversation. Just don’t be a one-hit-wonder and never crack jokes again after the first one. That makes it feel like a canned response which takes a lot of the fun out of it.

I can’t count the times when I made women who I met online laugh with my first message and then got a date out of it later. Although it’s not easy as it sounds because this does depend highly on your personality and sense of humor. That said, older women enjoy lighthearted messaging, so it works wonders if you're talking to an older woman.

If you don’t know any good jokes or can’t think of a great zinger while looking through her profile, there are many examples of funny first lines online that you can use.

Here are a few examples:

“I bet you could make a great living selling hot dogs because you sure do know how to make a wiener stand!"

“Do you want to skip all the bs and go on a first date with me so that we can begin this crazy magic rollercoaster ride of a romance right away?”

It’s okay to be sexual when starting a conversation with a woman

This is a great way to start a conversation online with women when you want to be more sexual and direct. That said, it’s so important that you don’t go over the top here. Being cheeky and playful is one thing. But if you push it too far at the start of the conversation, that’s a turn-off to most women.

Choose your audience carefully with this one and you’ll improve the number of women who are open to meet up with you, especially if you're on Facebook.

The other thing to be mindful of here is the vibe you’re giving off. It implies you’re looking for a hookup rather than a relationship. There’s nothing inherently wrong with that of course, just don’t expect all women to be into it.

As a good example, you can write something like:

“Hi there, cutie. What should we order for breakfast the morning after our date?”

How to Talk to a Girl Online

Now that we’ve covered how to start a conversation with a girl online, it’s important to keep that conversation going. The next step is figuring out how to keep that conversation going.

Be yourself

I know, it’s a cliche line but it’s popular advice for a reason. Experimenting is part of online dating. But if you’re creating a completely different character in your online conversations, it’ll all fall apart on the first date.

The better option is to be a playful, high-energy version of yourself. Conversations like that are fun and engaging and will definitely help your chances of getting those first dates.

That doesn’t mean you have to be boring

Just because you’re being yourself doesn’t mean you can’t have fun with it! We all have versions of ourselves that come out at different times. Think family gathering vs work meeting vs the bar with friends.

Get creative and have fun getting to know new people. Just don’t let that pull you into pretending to be something you’re not. If she’s expecting a certain type of person to show up on the first date and you turn out to be someone else entirely, things will go downhill quickly.

If you get stuck, ask questions

Sometimes you might find yourself with a bit of a lull in the conversation. Silence isn’t a bad thing but if you’re starting to struggle for conversation topics, get to talking about her.

Ask her some casual questions to learn more about her. Avoid things like “What are you studying?” and think more about what she does in her spare time or fun adventures from her last vacation.

As long as you aren’t asking boring questions or making it feel like a job interview, the conversation will flow easily. These topics are fun and she’ll find it easy to come up with answers since they’re about her.

Learn the art of conversation threading

Following on from that topic, conversation threading will help you become a better conversationalist in general. No matter what the two of you are talking about, virtually every sentence will have multiple topics for you to work with.

You can either stick to the current one and contribute or take it on a related tangent. Take this conversation for example:

You: “I miss traveling so much.”

Her: “Right? I spent most of 2020 in Boston when I was meant to be traveling Europe with my friend!”

From her response, there are so many directions you can head:

  • How you spent 2020 if it was similar
  • How did she end up in Boston?
  • Where was she planning to travel in Europe?
  • What type of traveler is she? 5-star hotels? Air BnB? Couch surfing?
  • Is she still planning to do that Europe trip?

There are so many more topics to pull from that sentence but you get the picture. With a bit of practice, you’ll start to see that almost every response is filled with potential talking points. This will eventually become a habit and you’ll find that you have infinite, engaging conversations without even thinking about it.

How to Talk to Girls on Dating Sites

To wrap up this article, I wanted to cover a couple more quick tips on talking to girls on dating sites. All the tips above apply but there are a couple more things to keep in mind in this context.

She gets a lot of messages every single day

Whether we like it or not, it’s a fact: No matter how attractive you are, most women are getting far more messages than you every day.

The good news is, most of these messages are boring, as we covered earlier. When most of those messages are some variation of “hi,” it doesn’t take much work to set yourself apart from them.

Slow down, take a minute to think things through and if you don’t have time to send a proper conversation starter, wait until later. There’s never a need to rush!

Don’t get needy or frustrated

This is a trap I see a lot of my friends fall into from time to time, particularly if they’re really into one of their matches.

They don’t get a reply for a day or two. So rather than leaving her to get back when she can, they start to push. They come in with the dreaded double (triple, or even quadruple) text and completely blow their chances.

Sometimes this can even lead to frustration, sending messages like “you could just say you’re not interested. . .”, as though that ever helped anyone’s chances.

Instead, it’s important to remember the culture around online dating. There’s never an obligation for people to respond to a message. And nobody wants to talk to that angry guy who demands a certain response time.

If she doesn’t reply, move on with your life. There are millions more women out there and focusing your energy on just one is unhealthy for you both.

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