Online Dating First Message

Online Dating

10 Online Dating First Message Do’s & Don’ts — (Plus Examples for Guys & Girls)

Hunt Ethridge

Written by: Hunt Ethridge

Hunt Ethridge

Hunt Ethridge is the co-founder and CMO of the as well as senior advisor and board of directors at other firms. He has been featured in well over 100 media sources and currently "coach on record" for most of the top matchmaking firms in the U.S. and internationally. You can follow him on Instagram or Clubhouse.

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Edited by: Lillian Castro

Lillian Castro

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For some, online dating is like perusing sweets in a candy shop. For others, it’s a slow and painful slog through hundreds of “nos.” Regardless of how we feel about it, online dating has lost its taboo and is here to stay. But dating sites are like gyms — sure, you sort of know how to use all of the tools, but you’re probably not maximizing them. And worse, if you do it wrong, you could actually be hurting yourself.

That first message is oh-so important. It can turn a “maybe” into a “yes” or “yes” into a “no.” My friend and client Sarah told me, “One guy wrote me an absolutely adorable poem about me after reading I was a poet. I probably would have ignored him based on his pics and profile. We dated for a month!”

So let me be your dating personal trainer and give you some do’s and don’ts of messaging.

1. Do Show That You Read Their Profile

I know most men and many women decide on whether or not to contact a person by their picture alone. I get it, but we’re trying to find long-lasting relationships, not just flashes in the pan. So take a minute and check out his or her profile. You don’t have to read the whole thing cover to cover, but skim it enough to retain some information about them. Then comment on it.

Good Example: “Hi there, I noticed you mentioned you like skiing. I grew up in upstate New York and skied a lot also, as the winters there can last almost eight months!”

2. Don’t Go Overboard & Get All Stalkery

Yes, it’s good to learn about the person and read what they wrote, but don’t go overboard trying to show that you read it. Too much interest too fast can signal that you are needy or desperate. Nobody thinks that’s sexy.

Bad Example: “I like your username, Pie&Tri! I like pie as well. I saw two of your pictures were of you on the beach. My favorite place to vacation is down in Florida on the West Coast where the beaches are beautiful. I also noticed your favorite movie is ‘The Notebook.’ I finally sat down and watched the movie last year, and yes, I absolutely cried as well. In the food section, you said…”

3. Men, Do Write a Little More

I don’t know whether it’s laziness, cost-benefit analysis, or just a numbers game, but so many men don’t take the time to craft even a brief note. Some actual messages from OkCupid I’ve found include “Your hot,” “DAm I got inch for you,” and “sup.”

C’mon gentlemen, let’s up our game a little. I know men aren’t as verbally communicative as women, but this is just not going to cut it. According to OkCupid, the ideal message length is only 200 characters, which is a little bit more than a tweet. If you’re actually looking for someone special, I think you can manage a minute’s worth of typing.

Good Example: “I love the fact that you have a picture of yourself at a renaissance festival! I’ve been to a few myself and I think they are a lot of fun. I love the axe throwing and mead. What’s your favorite part?”

4. Ladies, Don’t Write a Wall of Text

Yes, dating is all about getting to know each other, sharing, and learning, but there is plenty of time for that down the road. That time is not in your first message. You may have so much in common with each other that you just have to tell him all about it. Yes, you might have a funny story about the location of one of his pictures. However, right now, your goal is just to initiate a conversation. Your optimal length is actually 50 characters or less. So, in this instance, less is more.

Bad Example: “I love that picture of you at that funky wedding. My friends had one of those, too! Steve and Suzy were friends and former roommates from my time living in New York City. They were part of our first urban family that included Tim, Boffman, Stephanie, Jabroni, and more. They were both artists and really cool, funky people who had the biggest hearts we knew. So being able to attend their wedding up in New Paltz, New York, was awesome. I don’t know if you know New Paltz, but it’s this really cool, artsy little town only about an hour and a half north of NYC. Most people don’t realize how quickly it turns into country and green and grass and trees when you leave the city. The ceremony was beautiful in this little church. They had the back doors and windows open, so this beautiful breeze smelling of earth and blossoms and fresh cut grass was constantly wafting around us. Afterward, we…”

5. Do Check Your Spelling & Grammar

While this should seem obvious, I hear over and over again from my clients about messages that have misspellings and don’t use proper grammar. Online dating is all about first impressions. You always want to put your best foot forward. Having a message riddled with mistakes says either you’re lazy, uninterested, or plain old stupid. None of these choices are good. While I know we use a form of shorthand texting with our friends, this is not texting, and these people aren’t your friends. Take a minute or two and proofread before you send your messages. You could even use a tool like Grammarly.

Bad Example: “I want to you be more like my bestfriendt. If your the type of women that cant forget things easily, im not sure your for me. I love a sense of humor,laughter because i love to have fun. good enof?”

6. Don’t Play Amateur Detective

You may be really good at figuring out where some of the things in their photos are, and Google is great for sleuthing, but now’s not the time to showcase how good you are at learning about them before you’ve even met. You may think it shows effort, fun, and intelligence. However, it can come across as creepy, scary, and disconcerting. Save your insights for when you’re out together and the topic comes up.

Bad Example: “Hey there, I loved looking through your pictures. I’m pretty sure that pic of you in Central Park is up by 91st Street, right? And since you say one of your favorite places is Momofuku Milk Bar, I’m guessing you live on the Upper West side, right?!”

7. Ladies, Do Stroke the Ego a Bit

Over the years, men have been turned down by dozens, if not hundreds, of women. It can’t NOT take a toll on the ego. But we know it’s part of the whole experience. That said, it’s so nice to get a bit of a compliment from a lady. It doesn’t have to be anything big or pandering, and definitely stay away from anything that could be interpreted sexually. But if you want to stand out, throwing a little anti-shade his way couldn’t hurt.

Good Example: “Hey there BigBikingRyan! I love that you build your own furniture — that’s so cool. It must have taken a lot of practice and trial-and-error to get it right. Good job on sticking it out and getting good at it.”

8. Men, Don’t Comment on a Woman’s Body

Many women like to post pictures of themselves at the beach, and many women, while at the beach, wear a bikini, but just because she’s in a bikini doesn’t make it appropriate to immediately comment on it.

It’s not like you can go up to a woman in a bar and say “That strapless dress is so sexy. Let’s go on a date.” Your counter argument may be “Well, she put that picture up, so that means it’s OK to comment on it.” Not so. Just because you posted a picture of yourself up doesn’t make it OK for her to point out your beer belly or balding spot. Plus, it’s super creepy.

Bad Example: “I can tell you like the beach as you have a few pics up there. And you look fantastic in that red bikini — you should wear that every day! ;-).

9. Do Follow a Template in Your First Message

Here’s everything you should do in your first message to a match:

  1. Comment on something in their profile.
  2. Show that you have something in common.
  3. Ask an easy-to-answer question.

Good Example:

“Hey, StarfruitSurfer. I love that picture of you in the Alps. I also went skiing in Chamonix, good times! What’s your favorite ski place?”

10. Don’t Get Discouraged

Response rates to first messages, on average, are anywhere between 22% and 40%, so understand that the majority, and sometimes vast majority, of messages won’t get replied to. That’s fine, that’s normal. At the end of the day, it’s a numbers game, and if you don’t participate, you can’t win.

Make a Few Tweaks & See Drastic Results!

Most of the time, all your messages and profiles need are little tweaks to maximize your response rate, but don’t be static. If you feel something isn’t working, mix it up a bit. Try something different. And don’t burn yourself out. Remember, this should be fun!

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