Simple Tips for Starting a Conversation Online

A woman with purple nail polish starting a conversation online while typing on her laptop.

So, you’ve carefully selected the best photos for your online dating profile, you’ve matched them with a pithy “about you” section, and you’ve got a promising message (or several) in your inbox. Things are going well. But wait… Now what? You have to send a message. But how do you do that? Starting a conversation online, whether you’re kicking off or continuing an exchange, is easily the most intimidating part of online dating.

But here’s a secret: It gets infinitely easier once you write that first message. Keep a couple of key points in mind—which we’ve included below—and remember that practice makes perfect.

1. Tailor your message to your recipient.
“People almost always see themselves as unique,” researchers Khalid Khan and Sameer Chaudhry (from Barts and the London School of Medicine) note in their 2015 online dating study published in Evidence-Based Medicine. By that reasoning, the most effective messages are those that highlight details in the other person’s profile: a shared interest in favorite movies or books, or somewhere you both want to travel. So try asking the person to expound on an anecdote he or she mentions or create an inside joke between the two of you based on a point in their profile.

2. Keep things upbeat and funny.
Similar to the point above, you want to keep the conversation breezy and enjoyable. You don’t have to banter like a movie character, but you want to write something that makes the person on the other end smile. It shouldn’t feel like a job interview, so keep it light. Ask questions but also give out information freely or tell a story.

3. Don’t make it too superficial.
Women are not fans of messages telling them how beautiful or sexy they are and men often distrust messages praising them on looks or ambitions as well. As Khan and Chaudhry observe, “We routinely reject unrealistically positive views of ourselves, because this raises suspicion about about the motives of the complimenter.” You’re messaging someone because you’re at least somewhat physically attracted to them; no more needs to be said on the subject.

4. But flirting is more than fine.
Just because you’re not going over-the-top on compliments doesn’t mean you can’t still make the other person’s heart skip a beat. A look into online dating data from the online dating site Zoosk on how to write good online dating first messages suggests you use flirty words like crush and trouble—there’s nothing wrong with showing that this person has an effect on you.

5. Suggest date ideas.
As witty as your online rapport can be, no one signs up on a dating site just for a pen pal. The goal is to translate your chemistry from starting a conversation online into a real-life meeting; what better way than to start thinking about the first date right away?

Now, you don’t want to do this on the very first message, as that can be as impersonal as copy-and-pasting a generic message; you need a little bit of a back-and-forth to know what would be ideal for you two. Maybe there’s a movie you’d both be interested in, or an outdoor event in the local park? Maybe you just come out and ask, “What do you like to do on the weekend?” or “What are you doing after work this week?” Simple questions are the perfect way to transition the conversation from messages to a shared event.

6. Choose an ideal time of day to send.
The same look into online dating data, found that the best time of day for men to send an online dating message is 9-10 a.m., with women having more success around 10-11 p.m. Both genders won’t have any luck if they send around 2-3 p.m., likely because it’s in the middle of the day and recipients are less likely to be able to respond immediately or to pay much attention.

7. Mirror the other person.
This is a difficult one to remember: When staring a conversation online, your messages should match the other person’s in terms of length and tone. You wouldn’t want to dominate a conversation in real life, right? Keep room for a back-and-forth; ask questions to extend the conversation. And if you find that the last eight chat bubbles are your own, try asking a question and giving the other person a turn.

8. Don’t overwhelm with follow-ups.
94% of online dating message responses come within 24 hours. Of course, there are always outliers; people might be slammed in a particular week with work or personal issues. But you’ll have a pretty good sense, fairly soon after staring a conversation online, if the other person is interested. What you should not do is immediately send another message prompting a response; men who did so saw a 34% decrease in message responses, while women saw a 65% decrease. Harsh, but true. And that ties into our next point…

9. Be patient.
Don’t forget to keep calm and chat on. Half of all online dating conversations take five messages before both parties feel comfortable meeting up. Rushing the other person will limit your chances for a real date. Don’t see messaging as a means to an end, see it as a way to…

10. Have fun!
The best way to approach messaging is as an amusing challenge for yourself; as long as you write a message you’re proud of, you’ve succeeded. There will always be inexplicable reasons why someone might not write you back, and then one day someone will write you back, and you’ll meet in-person, and then…

Well then, you won’t care about much else but the time you’re spending together.

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