Top 6 Dos and Don’ts of Online Dating Messaging

Online dating messaging can be a daunting task of dating in the modern age. But there’s no reason to let it hold you back from jumping in. Learn how to message your way to a first date and beyond!

Online Dating Messaging

Fade In

Opening scene: Interior, bedroom. Night.

Our featured single is cruising online dating profiles in bed. Suddenly, they come across an amazing picture with an amazing profile. Our dater is visibly excited and clicks the “Message” button. They look up inquisitively, then begin to type.


I’m sure this is the beginning of your own personal fantasy movie that plays in your head when looking through dating site. But before you get to:

Exterior: Park, sunset.

Our couple walks into the distance, holding hands as they begin their life together.

Fade Out

…you need to make sure that you are sending the best message you can. In order to turn this movie into real life, here are my top Dos and Don’ts of messaging people online.

Do: Greet Them

Like any interaction, start with a greeting. It’s a warm up. Don’t just immediately type “You want to meet?” Say hello and introduce yourself. “Hi there StarFruit78, hope you’re doing well today!” Nothing crazy or complicated, just polite and well-structured.

Don’t: Copy and Paste

I know that you are probably contacting a lot of people. After all online dating is a numbers game. But one pitfall daters can fall in is too much “Copy/Pasting.” I know that you want to maximize your cost-benefit-analysis, but by saving time, you could be shooting yourself in the foot. It looks obvious and really only saves you a couple of seconds.

Do: Show You Read Their Profile

“Hey hottie, how you doing?” Ugh. Um, no. I know that you are just messaging them because they are hot. But you have to at least skim their profile. Find something that they mentioned, whether in the text or perhaps a photo and mention it. “I see you like to ski, so do I!” You are looking for that shared interest or common bond.

Don’t: Write a Novel/Haiku

According to neuropsychiatrist, Louann Brizendine, women use about 20,000 words a day while men use 7,000. This is something I always coach my clients on. Women, talk a little less, men, a little more. Same when messaging. Don’t just write, “Sup?” Likewise, don’t tell him your entire life story. Save that for the in person times. Here’s some math:

Men contacting women, 200 characters is ideal.

Women contacting men, 50 characters is ideal.

Check out more interesting stats from OkCupid.

Do: Ask a Question

The first few emails should be like a tennis game. I’ll lob you a quick and easy one, you lob me one back, etc. You always want to leave them with something easy to respond to, to keep the interaction going. But this is not the time to ask large questions. “When and how did you become politically active?” – No. “Fun plans for the weekend?” – Yes.

Don’t: Antagonize Them

Sure she might adore Zac Efron, and yes, his car is in every picture. But don’t go for low hanging fruit and say bad things about it. I know you might be teasing, but tone is lost in the black and white of email. Plus they got lots of messages. So if you tick them off, they’ll just skip over you and move on to the next.

Originally published in AMansQuest

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