The Art of Instagram Flirting

We all know the importance of using instagram to tell our story, showcase our style and build our online communities, and chances are you already have some pretty good ideas about how to do this for your own business.

But in the past few years of using the platform, I’ve discovered another lovely side effect thanks to my adoption of a little social networking tactic I like to refer to as Instagram flirting.

In my business, community is key and creative collaborations are one of my favourite parts of the job, keeping me challenged, inspired and pushing my skills in new directions while I build my portfolio and make a little magic. And a lot of these opportunities happen thanks to relationships I’ve built through Instagram and a little “flirting” with people whose work I admire.

There can be a lot of noise on social media, but there’s also a certain type of power in reaching out to potential collaborators and even customers, sharing the love and letting our intentions be known with those little digital hearts and a well-executed comment or two.

So if you’ve been crushing on someones Instagram content and are ready to take your relationship to the next level, I’m going to walk you through ways to reach out to your online “crush” to build an authentic, lasting relationship that will hopefully lead to a great first date, whether that looks like virtual cocktails over Skype as you share the exploits of a busy week, or an opportunity to work together on an upcoming project.

In the same way that we would take a little extra time to put together an outfit or do a little background research when we know we’ll be seeing someone we want to impress, here are a few guidelines to follow that I originally put together for The Rising Tide Society, ensuring you'll find your own “happily ever after”:


This isn’t about going through and liking every photo your insta-crush has ever posted. That starts to look a little spammy and is an instant turnoff. Instead, heart the photos you’re actually drawn to and that complement your own style. Chances are if you spend a bit of time scrolling through someone’s feed and liking a few choice photos in a row, they’ll notice and wonder who has been spending time getting to know their content.


You can go on an Instagram-liking spree until you’ve exhausted your thumb, but nothing makes a good impression like a personal comment.

Resist the typical “Love this!” or “So beautiful!” and leave a comment that speaks to the content, styling, or caption of the photo and is from the heart. We know how easy it is to spot an inauthentic compliment in real life, and when it comes to Instagram comments, the same goes. And though it might be tempting to write a lengthy comment, keep it short and concise.

A comment is worth a thousand likes, and a few well-timed, clever comments will go a long way, especially for someone who has a lot of updates to scroll through. Ask questions related to the post (or answer them, if relevant) and start a conversation.


Take a little time to share their content with your own followers by featuring them in a #followfriday post (or any day of the week, really), or tag someone you think would appreciate their content in the comments.


Get to know the object of your affection beyond their Instagram feed.

Find out what they’re working on and take the time to click through to their website or read the most recent blog post they’ve mentioned. The idea is to show your support and interest, and chances are their Instagram profile is only one piece of this. This could also offer up the opportunity to find out about a project they’re working on which you might be a good fit for, or other ideas for how you could collaborate in some way.


This isn’t a one-time effort, and even after your initial outreach, it’s important to continue to build the relationship by keeping up to date with what they’re posting.

Building a relationship takes time, and there comes a time when it’s time to take your relationship to the next level and send them a DM or even - gasp! - an email. Big steps, I know, but Instagram isn’t a messaging app and as soon you’re ready to have a conversation that includes more than a line or two, you might want to shift your efforts accordingly.


Just like flirting IRL, Instagram flirting should be fun and true to who you are. Be yourself and do what feels natural, letting your personality shine through.


In the same way that, whether we want to admit it or not, we judge a book by it’s cover and our first impression of someone is made within the first 15 seconds of meeting someone, we have a very brief window when someone clicks on our username to capture their attention and get them to click that little “follow” button.

Take the time to optimize your profile and plan your Instagram content so that it represents your brand, making sure that at first glance a new potential follower gets a sense of who you are, what you do, and what your style is. This means paying attention to your profile picture, your bio and of course your Instagram feed itself.

Make sure those top nine photos represent your brand and some of your best work. A simple way to tackle this is through the use of colour to create a consistent brand presence. You want your style to be evident at a glance, and in the same way that you were attracted to their content and what they have to offer, you’re hoping for the same reaction from them.

Looking for a little help in coming up with Instagram content and for a way to connect with other creatives in the Insta community? I've got a free challenge that helps you do just that!