6 Ways to Approach Someone You Want to Be Friends With

Making friends when you’re young can be as simple as sharing a toy or deciding that we’re suddenly “best friends.” But the older we get, the significantly less straightforward it becomes — at least it can feel that way. It’s probably been a while since many of us had to put ourselves out there. We might feel out of practice and, at the very least, a little confused about what we should actually say to someone we’d like to get to know better.

There isn’t one right way to approach someone you want to be friends with, but here are a few ideas that might help.


1. Highlight a similarity

Friendship is born at that moment when one person says to another: “What! You too? I thought I was the only one.” – C.S. Lewis

It’s true what they say; the root of friendship is often an underlying similarity, whether it’s a shared interest, hobby, or sense of humor. That’s why pointing out something you have in common is a great way to approach someone you want to be friends with. Commenting on your shared love of hiking, sushi, or jazz music shows that you’re paying attention to and are interested in the other person and can set the stage for future conversations and outings, and a friendship. The key is to not force it. Avoid exaggerating and don’t try to be someone you’re not. Noticing and highlighting genuine similarities will not only make you feel more comfortable approaching someone, it’ll also help you come across as authentic and increases the chances that you’ll actually hit it off.


2. Ask them a question

Asking someone a question is another option. But if you really want to have a chance at sparking an actual conversation, it’s best to avoid questions about the current time or weather. Come up with thoughtful, open-ended questions, ones that you actually care about learning the answers to. Ask for a specific restaurant recommendation, a new workout class, or the best nearby cafe to work from. If it’s someone you know a little bit, ask for feedback on something you’ve written or created. These kinds of questions show that you have an interest in the other person’s opinion, which suggests that you trust them. They also give a glimpse into your own personality and make follow-up conversations — like chatting about how that exercise class went or even suggesting that you go to one together — a little easier!


3. Pay them a compliment

Compliments from strangers or people we don’t know that well can be so powerful. They are often unexpected and deeply appreciated. That’s why it can be such an impactful way to approach someone we want to be better friends with. It might feel easier to compliment the things that are obvious, like physical appearance or style, but if you feel up to it, make it something a little more personal. Compliment their work ethic, creativity, insightful comment, compassion, or great laugh. Explain what you love about it and why it moves you. These kinds of genuine, perceptive compliments are the ones that stick with us. And moving beyond the superficial can make people feel seen and heard in ways that really foster connection and friendship.

The one caveat: When it comes to compliments, it’s best to avoid going overboard. Usually, the more you give, the more insincere they can start to feel. And ideally, most of us want friendships that are based on balance and equality, not adulation.


4. Offer help

One of the main things that separates good friends from casual acquaintances is the ongoing emotional, practical, and social support. That’s why letting someone know that you’re there if they need help, (e.g., solving a problem with a school or work assignment, or even with some heavy lifting) is a great away to approach them and subtly let them know that you’re interested in being friends. This can work out especially well if you’re able to work together toward a common goal (e.g., like train together for an upcoming race). Sometimes, offering tangible support or having a concrete goal in mind can make it easier to approach someone in the hopes of becoming better friends.


5. Use humor

This approach isn’t for everyone, and it can be harder to pull off if it’s not something you’re used to. It’s not about knock-knock jokes and it’s definitely not about trying to show off your wit or charm. It actually has very little to do with impressing someone else and everything to do with trying to make both of you feel more at ease. Sharing a lighthearted comment or joke, your penchant (pun-chant?) for puns, or your tendency to be self-deprecating gives the other person a glimpse of your personality and can be a great way to connect. Just remember, it’s best to avoid putting someone else down, even in a joking way. And don’t be too hard on yourself if your humor doesn’t land. At the very least it can be a helpful litmus test for seeing whether you can bond over your sense of humor!


6. Be upfront

This last strategy is the one that can make us feel the most vulnerable. It’s hard to put yourself out there and to worry about possibly being rejected. But when you feel like you have the most to lose, you most definitely have the most to gain. If you’ve had only brief interactions with someone you want to get to know better, it’s absolutely okay to share that you’re looking to meet new people and that you’ve really enjoyed the conversations you’ve had so far. Being direct about your desire to make new friends doesn’t have to be a big scary thing. Casually let them know that you’d be happy to chat again or get together in a different context (e.g., “Hey! I really enjoyed our conversation! Any chance you’re open to grabbing a coffee sometime?” or “I actually just moved here and don’t really know anyone. I’d love to find a time to hang out and maybe go for a walk together!”). People are often far more receptive to this than we expect. They might even be relieved that you made the first move!


Regardless of whether you are upfront about the fact that you’d like to be better friends or prefer a more subtle approach, keep in mind that it is a process. It takes time, patience, vulnerability, and repetition — which means plenty of opportunities to practice these different approaches!


What do you think is the best way to approach someone you want to be friends with? Have any of these strategies worked for you? Let us know in the comments below!


This article was originally published on July 19, 2017.