5. Chatting Online
5. Chatting Online

5. Chatting Online

Communication to a relationship is like oxygen to life. Without it… it dies. — Tony Gaskins

First of all, congrats! You should now have your optimized online dating profile ready to go and have the dating algorithm on your side. In the next few days, you'll start to see a surge of potential mates!

But as a reminder, the end goal of this guide isn't just to increase the number of likes you get. The real end goal is to turn online relationships into offline relationships—potentially for life.

Therefore, everything you have learned so far has led up to this page. Here's the process on how to chat online successfully in three steps:


Your conversations will always start with the hook, then the medium, and end with the ask. Like before, we'll break down each step into digestible, actionable pieces of information that you can start using it today.

1. The hook

This step is just what it sounds like: how you catch their attention. Note that your hook is the most important part of the process. A bad hook means no conversation and no conversation means no chance. To start, all pick-up lines can be broken down into three:

1️⃣ Direct

A direct pick up is exactly that: direct. An example would be "I find you attractive, want to go on a date?"

2️⃣ Innocuous

Acting as a conversation starter, innocuous pick-up lines sounds something like "What's your favorite drink?"

3️⃣ Flippant

These pick up lines use humor and creativity to grab someone's attention like "I'm hot, you're hot, let's make out"

According to several studies, direct pick-up lines (option 1) works best for most people most of the time. Innocuous lines (option 2) work some of the time and flippant lines (option 3) rarely work [1, 2, 3].

Which option you choose will depend on what you feel comfortable using but we recommend being direct. As an example, here's "John's" default hook (pick-up line) that he used to start conversations with most of his matches:


It doesn't get any more direct than asking "Coffee date?" for a coffee date.

As an added bonus, John (as a beta-tester) was able to use the research from the previous pages to put pictures of his dog, something most people find attractive [1, 2].

Other examples of direct pick-up lines would be "I found you attractive, can I treat you to a burrito?". Notice that where you take your potential date is specified, in this case, to eat Mexican food together.

Direct really means direct. Be as specific as you can to follow along with the research we've already outlined before. To echo what you already know, be clear about your intentions!

Something else to add to your direct pick-up line would be some kind of positive aspect you have [1]. This could include—as per the research—mentioning that you have a dog, that you take care of children or any other positive attribute. An example of this would be "I find you attractive. Want to go on a date at the park with my dog?".

If you have any questions about pick-up lines, you can ask away here. We want to make sure that everyone who reads this guide leaves with the "how-to" of good pick up lines—they are the most important part of the process.

2. The medium

This part encompasses everything between the hook and the ask. The medium is the bridge between making your online relationships into offline relationships. Pay attention!

Every single medium you carry out online will be different depending on your chosen pick-up line, your interests, their interests, the context, etc. As such, there is no cookie-cutter recipe for success.

But, there are a few dos and don'ts you should keep in mind during the medium step. While these won't make or break your chances of getting their number, every detail counts! Let's start with the dos of the medium:

Use metaphoric language

Hear us out. Instead of saying "your eyes are pretty", say "your eyes sparkle like morning dew". Weird, but it works [1].

Take rejection gracefully

If there's no answer to your pick-up line, move on. Your time is better spent on others who are actually interested!

Use good grammar

According to Match.com's annual survey, Singles in America, good grammar topped the list (83%) as one of the most important qualities people looked for in a significant other [1]!

It was more important than confidence or attractive teeth, so take your time and spell everything right.

The don’ts of chatting online

Now for the don'ts of chatting online. If you have any additional ideas for this page, let us know and we'll add them!

Comment on looks carefully

While it's generally distasteful to comment on other's looks, a recent study showed that some people really liked it when others pointed out their phyique—especially fit men and women [1].

But, be careful. According to a recent survey, a majority of people in the United States are unsatisfied with their body image [1].

Don't force the conversation

If you feel like you're carrying the conversation on your back, it might be time to move on.

Chances are that even if you meet this person in real life, you'll go through the same ordeal face-to-face.

Don't be creepy

This goes without saying, but don't outright ask questions like "where do you live", "what are your parents' names", or even "what underwear are you wearing".

Echoing the wise words of Professor Oak, "there's a time and place for everything". You can ask kinky questions after you get their number.

Keep up to date with this guide

If you haven't already signed up for the newsletter (how did you even find this guide?), you can fix that by clicking here.

We'll send you an email every 3 to 4 months notifying you about the new research!

We have no doubt that your first few attempts at the medium will go bad—it went terrible for the beta-testers at least. But with practice comes perfection. Do not give up after the first few attempts. Every single one of your failed mediums will teach you what works and what doesn't.

3. The ask

So, you've sent out your hook, they've answered, and now 20 to 30 messages have passed during the medium. As a reminder, you want to wait until at least 20 messages have been exchanged before asking for their phone number [research on the previous page].

Asking for your potential mates' phone number is a risky affair. Once one of you has sent over those magical digits then the fun really begins!

It's important that you don't mess up the ask. Giving your contact information is a sensitive matter for both of you—it shows that at least one of you trusts the other with their contact information.

Like in the hook, the best way to ask for their phone number is to be direct. The literal question of "What's your phone number?", at least for the beta-testers, worked most of the time.

If you feel uncomfortable being too direct you can couch the question with a casual excuse. For example, you could say "I don't check this app very often. What's your number?". This worked for the beta-testers most of the time as well.

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