Should You Use Emotes When Dating Online?

When you’re dating online, every single impression you make counts. So the question eventually becomes: are emoticons cute, or immature? Do they help clarify your conversation, or do they just make things even more confused? This might seem like a minor touch, but women will use almost any excuse not to answer a message. If you don’t make the right call you could be “winky-face”ing yourself out of a great date.

When You’re Trying to Joke

"She will laugh out loud - literally!"

“She will laugh out loud – literally!”


Tone is very difficult to convey online. What might seem like a harmless joke to you could be harsh to her. She might not realize that you’re having a laugh about something and think that you’re serious. When you’re trying to joke, tease, or use sarcasm an emoticon can actually help clear that up. “Nooo, I hate that band! ;P” is a lot different from, “Noo, I hate that band!” If you’re saying anything that shouldn’t be interpreted literally, it doesn’t hurt to throw in a smilie face at the end to make it clear to her that you’re kidding. Later, when you know each other well enough to catch a joke you can try dropping them if you want.

Too Often Looks like You’re Trying Too Hard

"She thinks you are desperate and will show your messages to her friends"

“She thinks you are desperate and will show your messages to her friends”


When you’re using an emoticon at the end of every sentence you seem both immature and desperate. If the number of emoticons rivals the number of words that you’re sending you’ve gone way, way too overboard. They’re also not like closing punctuation. Not every sentence needs one. Emoticons are sort of a grey area for most people, but there is one way that everyone agrees with: when you use them too much, you look like a teenage girl. That’s not going to make the best impression on the woman you’re trying to woo with your words.

Stick to the Basics

In general, stick to the basics when it comes to emoticons. Using the standard smilie face every now and then shouldn’t hurt your chances with any reasonable woman. Even a 😛 or a 😉 for spice every few messages won’t hurt her. What you want to avoid are the ones whose meaning isn’t immediately clear. What does ^(O,O)^ mean? (We think it’s an owl. What we don’t know is what human emotion an owl is supposed to be expressing. Insomnia? The desire to eat rats?) If she has to check an online emoticon source to figure out what you’re trying to say, the odds are good that she’s not even going to bother. She’s going to assume that you’re immature and not ready for a relationship, and she’s going to go out with a man who can compose a whole message without relying on cartoons or symbols. It’s not fair, as you were probably just being cute or making it easier for her to understand, but it’s how the world works.

Emoticons are like a fine hot sauce. In moderation they will make everything better, spicier, and more memorable. Slather them on and you’re going to ruin everything and have some major regrets the next day.

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