Back to the Basics: How to Craft a Great First Message to Someone You’re Interested In

Did you know 20% of singles in the United States call upon the help of others to draft a message to someone they’re interested in?! And an astounding 49% of Gen Z (ages 18-24) is guilty of calling on their squad to help craft their first message to someone they like.

Photo by Timi David Fregene on Unsplash

We have all probably asked for help at least once. I get it,  figuring out what to write to a total stranger can be a daunting task and often a road block for those entering the dating scene. Questions I often get asked by my single friends are:

  • How long should my message be?
  • Can I just say “Hey”?
  • What do I talk about?
  • Do I send them a compliment?
  • How do I stand out?

All really great questions and ones that I will address today to hopefully make your messaging experience a little less nerve-racking.

So let’s start shall we:

How long should my first message be?: I wouldn’t worry too much about length, however, I wouldn’t write an essay to start. I think a short and sweet first message is always the best way to start a conversation. Remember, you want to slowly get to know one another, you don’t want to give too much information away to someone you’ve never met before. Even though you may be attracted to their profile initially, you may not hit it off once you start chatting.

Can I just say “Hey”?: I wouldn’t recommend just tossing out a “hey”. Surprisingly a lot of people do this, I think because it’s fast and easy, but it lacks effort. If you’re truly interested in finding someone, you’ll want to put some time and thought behind you’r first message. And by time, I don’t mean hours thinking of the perfect thing to say. Crafting your first message should take no longer than 3 minutes max!

My number one piece of advice, which is also backed by research, is to send a message that refers to a shared interest or experience. When POF asked singles, “what is the type of message you’re most likely to respond to?” 60% of singles said, if the message highlighted a mutual interest or experience, they would most likely respond.

What do I talk about? Take a look at their profile and try to find something that interests you – do they like a certain sport, do they have a pet, do they give a list of emojis of activities they enjoy doing? Find something, anything that you can spark conversation off of. Some people may be more the mysterious type who write “Ask me anything.” In this case, start with the basics.

  • I’m so sad summer is coming to an end! Did you do anything fun this summer?
  • From your pictures it looks like you travel a lot, have you gone anywhere recently?
  • Would you rather pizza or sushi? Coffee or tea? Star Wars or Star Trek? (You get the idea)

Do I send them a compliment? Sending a compliment about someone’s photos and appearance was ranked #2 (18%) on the list of messages most likely to get a reply; however, this percentage is significantly less than shared experience or interest. I think pairing a compliment with one of their interests may be the best way to approach this type of message. It will be evident that you’ve scoped out their profile beyond their photos and picked out something you really liked about them outside of their physical appearance.

How do I stand out?: Refer to everything I’ve mentioned above, but also take time to look at your own profile and see if you have enough information for someone to spark a conversation from. The more hobbies/interest you include in your profile description, the more material you give someone to reference during conversation. Maybe you even share you’re favorite quote or a funny short story that happened to you recently.

Think about it, if you were to receive two different messages – one from someone who had a shared interest listed on their profile and the other from someone with a blank profile description, who are you more likely to reply to? I’m going to go with my hunch and say the first.

Don’t overthink the first message because according to Plenty of Fish research, 85% of singles are willing to give someone a second chance should the first conversation not go well. Phew!

Kate Maclean

Posted by Kate Maclean

Kate is the PR Generalist at PlentyOfFish. Like a kid in a candy shop, Kate’s favorite things to do are eat mass amounts of sushi, spoon her cat Snoop Dogg, and hike the great Canadian wilderness. Her favorite quote of all time is “People who love to eat are the best people” -Julia Child.

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