Instagram pick up: How to flirt on IG

Almost two years ago I wrote a piece on why you shouldn’t try following people from dating apps like Tinder and OKC to their Instagram page. Today, let’s look at the flip side – how to flirt on Instagram. What do you need to know before you slide out from Tinder and into her DM’s?

ainbow haired woman made by Ai Midjourney.  Is she an instagram influencer?  should you slide into her DMs to flirt?  How to flirt on instagram
Instagram babe created by Ai Midjourney

How to Flirt on Instagram

Read the room

Appreciate that if you follow them from off the dating app to their Instagram, you are no longer in a virtual nightclub- you’ve come to their place of business, and approached them at a time when they are doing business, not necessarily in the mood to flirt.

Have some appreciation that it comes off a little creepy, impatient and entitled. You’ll need to work hard to overcome this.

Start from scratch

Instead of starting with ‘I followed you from Tinder, ask me questions’ put a little work in to build rapport and don’t even mention the dating app. Show you can conduct yourself appropriately to the internet environs in which you have approached your intended beloved.

Man and woman having a fight.  Not all women want you to message on instagram and flirt with them, especially if you do not reveal anything about yourself
Midjourney Ai

Rebuild your own shop window

Build yourself a really great Instagram page, with photos that show you, what you look like, what you are into – by leaving the dating app you’ve abandoned your profile, or shop window, so the woman has no idea of anything about you to get an impression of you to decide whether she is interested. This is more than a list of statistics- she needs to get a sense of what you are like as a person.

Thirsty boys drink last – how to flirt

Build your flirtation naturally- just because a woman is on a dating app it doesn’t mean she wants to date everybody or that that is how she spends most of her waking hours. You’ve followed her to a place where she is her non-dating self. That’s the person you are meeting online. Whether its Guardian Soulmates or Fabswingers, everyone has many sides to themselves. Just as you yourself may be on different apps, don’t use the image of the woman you have built in your mind to believe you can circumvent normal process and courtesy. Nobody enjoys being treated like a sex object by an unknown stranger (well maybe a few do, but all the ones I’ve met are men).

latex clothing on womans body made by Ai.  Do you like to follow people to instagram to try to flirt?  How to flirt better if you want to slide into her DMs on IG
Ai Midjourney

You really wanted to know to to flirt on Instagram

Have appreciation that you have circumvented the ‘easy out’ option she has of just not swiping right on you. You are forcing her to tell you no directly, block you or otherwise. As well as the fact nobody likes to hurt someone’s feelings, the fact is that almost all the people you approach in this way are going to be a no. There are a number of reasons for this, above and beyond the worrying suggestion of lacking healthy boundaries and social graces that the platform switch involves.

You may be out of her preferred ranges- for location, height, age, many things. Perhaps she didn’t like the impression you gave from your profile write-up on the app. Perhaps you just didn’t give the impression of whoever it is she’s looking to meet at the moment. In any case, appearing on her Instagram doorstep with a few vital statistics doesn’t really paint the scene that is needed to capture a woman’s romantic or sexual interest. And now you are forcing her to tell you no directly instead.

Ai image of a face glowing.  Does IG technology make you feel protected when you want to try to flirt on IG?  how to flirt on instagram without being creepy is hard
Midjourney Ai

#Notallmen? Instagram pick up

I’m hoping that all the men reading this are one of the good guys. One of the guys who doesn’t hurl threats and insults at women, evoke violence, lose control, demand and throw your weight around to try to get what you want. The measure of a man is in how he behaves when he doesn’t get his own way. Let’s hope you are all the evolved, blessed examples of positive masculinity we so need in this world. And, as such, hopefully you will understand that not all other men are so serene and chivalrous as you.

Emboldened by the barrier of a screen and keyboard, with a little hurt ego, I can unfortunately assure you that there are a huge number of men who are most unpleasant to women, in person as well as online. And when someone follows you to your Instagram (which might show your friends, village, or your own physical shop) and starts making threats to hunt you down for revenge?

That isn’t something we can always guarantee won’t translate into us becoming yet another tragic statistic. So know this. Know it isn’t an occasional thing. Know it happens to pretty much all of us, and for many it is pretty much all the time. So when you are the 10th guy that week on the Tinder-to-Instagram trail, kindly popping up to ask us out and impress us with your no-nonsense problem solving skills and expecting us to be really flattered and interested? Use your smarts that got you this far to reframe your final approach. How to flirt on Instagram? Like a gentleman.

How to flirt on Instagram: The perfect approach?

My perfect way to be approached on Instagram? Not to be. Flirt with me on the dating app, where I’m in the right headspace and we can both see whatever we need to know to decide and nod or pass quietly. Second to that? Make it look natural. Like I was a girl working in a book store and you just wandered in and we got chatting (I feel like this might have been a TV series…) After all, women enjoy hunting as much as the menfolk. Show yourself worthy quarry, let us come to you when we want to and don’t spoil our fun.

Happy hunting baby ducklings



Your guide to success on the swinger scene: pick up, threesomes, profiles, events and party hosting