How To Start An Online Dating Conversation

Attention-grabbing profile, check. Strong pictures highlighting all your best traits, check. You’ve got all the pieces to the online dating puzzle in place – now it’s time to take the plunge and start a conversation.

A quick Google search will reveal there are tons of guys who already know how difficult it can be to get a woman to reply to them, especially if she’s attractive. If you don’t know the best way to start an online dating conversation, it could take you awhile to get a response.

stressed out by online dating?

In fact, statistics show you’ll need to a whopping 114 messages just to be 99% sure you’ll get one reply.

But don’t worry – here at VIDA we’ve crafted thousands of messages and tracked their response rates, so we know what works and what doesn’t when it comes to sending messages that make her want to write you back.

Exclusive Bonus: Download our 5 favorite conversation starters to get immediate response from attractive women.

Get ready to take some notes, because we’re about to share everything you need to know about starting a conversation that will end with a date – including some great examples of online dating conversation starters!

Step 1: Gather Some Intel

Once you’ve found someone that catches your eye, look through her photos (as if we had to tell you that). This is often the best place to figure out her personality, since her photos are an indication of how she wants to present herself.

If she uses a professional headshot as her profile picture, you might conclude that she wants to be taken seriously. If she uses a picture of her ziplining through the jungle, you might try to appeal to her adventurous side. You get the idea…

Next, skim through her profile. Try to pick up on what she is passionate about — she'll be more apt to respond if you ask her about something she’s interested in. Also take note of things you have in common. If you ask about something you are mutually interested in, you'll have a much easier time keeping the conversation flowing.

PRO TIP: No time to read through the profiles of all the attractive women you want to message? Here’s a shortcut that will save you tons of time on dating sites and apps: use cut & paste messages that you can send any woman. Keep reading for some examples. Or take the most efficient route of all, and let us do it all for you.

Step 2: Send An Icebreaker Message

bad Tinder pick up line

If you’re one of those guys who’s been leading with “Hey, baby” or “ur beautiful”, you already know that doesn’t work.

Your message needs to grab her attention, pique her curiosity, and make her want to know more about you. You also want to make it easy for her to respond, and the best way to do that is to ask her a question.

First of all, you need to come to the table with a conversation topic. A thought provoking, fun, playful message that stands out from all the lame messages cluttering up her inbox. This is where the intel you gathered comes in.

For example, if she’s an athletic type who filled her photo section with pics of her bombing down the ski slopes, try something like this:

skiing Tinder message

Use the advanced search criteria to find women who like to ski, then send that message to any of them who interest you. This works for any keyword, like travel:

weekend Tinder message example

Here's a conversation starter that's almost sure to get a response if her dog makes an appearance in her profile or photos:

first message to start a conversation

You can send an icebreaker like this one to just about any woman, as who doesn't like to think they've got a well-developed sense of adventure?:

conversation starter for tinder

This message also has copy and paste potential, because thinking about dessert is popular across the board:

question to ask on Tinder

Once you come up with a few good copy and paste messages, test them out and keep the winners. And it’s surprisingly easy to come up with some good ones, if you keep these DO’s and DONT’s in mind:


    • Make it easy for her to respond by asking a question in your message.
    • Base your question on information that you gathered from her profile.
    • Use proper grammar and correct spelling – you only get one first impression.


    • Compliment her looks (that’s what all the other guys do, and it doesn’t work for them either).
    • Write multiple paragraphs. She’s not going to read it, and you don’t want to look like you’re trying too hard to impress her.
    • Ask her out in the first message, she wants to get to know you before meeting you in person.

Step 3: Follow Up If She Doesn’t Respond

What if, despite your best efforts, she doesn’t respond to your icebreaker message? Don’t worry – it happens. Maybe she’s busy. Maybe she forgot, or she’s out of town.

After a day or so, send her one more message. You want to let her know you’re genuinely interested, but you don’t want to appear desperate for her response. That’s  major turnoff, so keep it light-hearted:

follow up Tinder message

If she doesn’t respond to that one either, let it go. You don’t want to look like a stalker, and besides – there’s plenty more fish in the sea.

Step 4: Know When To Ask Her Out

When she responds to your icebreaker, there’s an easy formula to keep the conversation flowing towards a date:

    1. Comment on her answer to the question you asked.
    2. Answer it yourself so she learns something about you as well.
    3. Ask her something else.

Use every message as an opportunity to highlight your positive qualities and traits – the whole point of an online dating conversation is to build attraction.

woman holding up a sign that says HOT

For instance, if she asks you about your plans for the weekend, you could mention how you’re planning to take your dog on a hike, take your nephew to a ballgame, then meet some friends for a concert.

In just one sentence you’ve communicated that you’re responsible enough to have a pet, you’re active, you’re family oriented, and you’ve got a social life – all attractive qualities.

But how many messages should you exchange before you ask her out? You don’t want to pressure her or scare her off by asking too soon, but you don’t want her to lose interest by taking too long or asking too many follow-up questions with no end in sight.

After all, she’s not on Match.com to find a new pen pal!

Luckily for you, our team of modern dating experts reviewed thousands of online dating conversations that resulted in dates for our male clients. After examining the data, we learned the best time to ask for the date is after she’s sent you 2 or 3 messages.

But to get her to say yes, you have to ask her out the right way. Preface your question by making a statement you're certain she'll agree with, as that puts her in a “yes” mindset, then give her two date choices:

great way to ask her out online

Never just suggest meeting for drinks – doing that will torpedo your chances of success. For even more essential tips on how to ask a girl out online, click here.

Don't want to leave anything to chance? Have the dating experts at VIDA handle all the messaging for you! (And everything else, too!) Get more details here.

About VIDA

VIDA is your very own team of experts who set up high-quality dates for you so you can finally meet your ideal woman. Say goodbye to the hassle and frustration of online dating - we'll craft an irresistible dating profile, send engaging messages, and even book your dates for you. Thousands of guys have already made lasting connections with beautiful women, and we're ready to make you our next success story. All you need to do is schedule your free confidential consultation with us now.

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