5 ways to reach out to someone without feeling weird

Have you ever wanted to reach out to someone but didn’t quite know what to say? Maybe it’s a friend you’ve fallen out of touch with, or someone you know in passing but would like to get to know better.

It can be scary to be the one to reach out. Especially with someone you don’t know very well.

As much as we want connection, we also don’t want to put ourselves (or the other person) in an uncomfortable position.

“Will I be bothering them if I reach out?”

“We haven’t talked in so long, what do I even say?”

“Is it weird to reach out after all this time?”

The fight between “I want to talk to you” and “I don’t want you to think I’m weird” is SO real.

And a lot of the time, “I don’t want to be weird” wins out.

We don’t risk making the first move, we put it off for another day, and ultimately…

We never reach out.

We don’t make the connection, and we lose an opportunity to get closer to someone who might have a lot to offer us, or that we could offer them.

Sending the first message is the hardest part, so I wanted to share some of my favourite ways to do it.

You can steal the examples directly and just adjust them based on your relationships and preferences!

I hope this inspires you to reach out to someone you want to reconnect with, without worrying too much about the “how”!

  1. Reference something they’ve told you. What big life events have they mentioned? Anything they’re excited about? Were there any big decisions they had coming up? Things they’re reading?

    💁🏽 “Hey! I remember you mentioned you were moving to the Distillery last month. How was the move? How’s your new place?”​
  2. Mention something that reminds you of them. Have you read an article or book that reminds you of the person? Or been somewhere, talked to someone, or faced a similar challenge that makes you think of them?

    🙋🏾‍♀️ “Hey! This is super random but I just went to see the new Van Gogh exhibit and it reminded me of what you said about his Starry Night painting. It’s been a while! How is everything?”​
  3. Acknowledge the distance and ask to catch up. Check your last emails, text messages, or social media exchanges to see what you last talked about and when. Then just be direct with wanting to catch up!

    🧑🏻‍🦰️ “Hey! It’s been a while since we’ve caught up. I think we last talked in the spring before everything started to shut down. Can’t believe it’s been so long haha! Catch up coffee soon?”
  4. Connect over a piece of content they’ve put out. You can use this as an opportunity to commiserate, ask questions, show your appreciation, or ask for more information on what they’ve written or talked about. It’s easier to reconnect over something you know is currently top of mind for this person!

    🙋🏻‍♂️ “Hey! I just saw your post on LinkedIn about dealing with burnout. Thanks for sharing that, a lot of it was sadly familiar haha. How are you doing?”
  5. Share something that might be helpful to them. How can you help this person solve a problem they’re facing? Can you make a useful introduction? Share an upcoming event? Answer a question for them?

    👩🏽‍🦳 “Hey! How’s everything going? Were you still looking for a new yoga mat? I got the Lululemon one a couple of weeks ago and it’s been great. Thought I’d share in case you’re still stuck.”

Can you think of someone you want to reconnect with? Give one of these messages a shot and let me know how it goes!

P.S. I know creating and maintaining connections can take a lot of time and effort. So we built Good People, a community that’s specifically made to foster connections through small groups and shared experiences! Take a look at our upcoming cohorts (starting later this month!!) and come join us.



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