While I have not yet created a submission box for my advice column, I am blessed to receive text messages and DMs on the daily from friends (or randos) asking me for help with their sex and love lives. When a friend of mine texted me for advice on how to slide in a girl’s DMs, I couldn’t resist posting it on here because I figured lots of dudes (and chicks, too, perhaps) could find it useful. So, here you go — thank me later.
First, here’s the actual text exchange if you prefer to read it this way, but I’ve written it out below and will be expanding on the advice I gave (and explaining why it’s the best advice).
Hey! I have a SUPER random question for you, but it’s a topic I felt like you’d get more than anyone else I know, haha. It’s about shooting your shot via Instagram DMs. This girl I follow (not sure why I follow her) is a blogger, but more importantly seems kind of cool (I think) and pretty cute. She likes my pics from time to time, doesn’t have 8 million followers, etc. So, question is, how can I slide in her DMs without seeming like a creep. Also, that last point about liking my pics is now making me cringe a bit.
I think the way to do it, based of off what’s worked with me, is to play the long game. Instead of coming into her DMs with a pointed message asking her out, randomly DM her in response to her stories and go from there. I think it will eventually turn into a longer convo (and if it doesn’t — probably safe to say she’s not interested) which will give you the “in” to ask her out naturally.
How do I know this works? Because it’s worked on me.
Basically, one of my “mutuals” (that’s a term for someone you follow who also follows you back, in case you didn’t know), would randomly DM me stuff in response to my stories, such as, “Oh, you’re in Denver you should go to this place,” or “dope shoes,” or even “🔥” maybe sometimes.
I’m not sure how he started following me, but I thought he was cute and looked cool (plus saw that he worked in the same industry as me), so I followed back. This is also key. If she doesn’t follow you back, she might not even see your DMs because they might be relegated to the graveyard of DM requests. Your well-intentioned message will get lost among all the “nice bobs” and dick pics. And you probably don’t want to keep DMing her if she doesn’t respond to your first one (or two at most), because then you’ll just look like a creep (and tbh, you might be).
Also, if a “blogger” or girl who clearly cares about her follower/following ratio and Instagram presence (which is honestly almost every girl these days), follows you, that is a very good sign, because she likely doesn’t follow just anyone.
That being said, her “liking” your photos from time to time probably doesn’t mean anything unless she’s liking your pics from three months ago (and therefore is Insta-stalking you and doesn’t care if you know it— a great sign for you). People who are trying to build their Instagram following literally just double-tap every photo that comes up on their feed. Many of them take the time to “like back” many of the people who like their photos as well. So don’t take her “likes” personally, sorry.
Anyway, back to the guy who used this technique on me. I never thought of him as creepy (he probably didn’t lead with the fire emoji), or even thought about him being into me. Eventually we started having a longer convo one night and he said something like, “in case you weren’t aware, if you lived in NYC I’d date the shit out of you.” I don’t know if it was the fact that I was home alone and lonely on a Friday night or that the combination of the words “date” and “shit” were so endearing, but I liked that he said that, so I told him I was actually going to NYC in a few weeks and we proceeded to plan a date.
By playing the “long game,” it separates you from all the other dudes who are coming in her DMs immediately leading with some pick-up line (or worse, the lone “hey” or emoji) as if they were on Tinder. Building up the dialogue will also make you look like less of a predator and is almost the Instagram DM equivalent of being “friends first” before fucking.
If you’re really trying to win her heart (yes, I realize her heart is probably not the body part most on your mind), you should read one of her blog posts (or at least one of her long captions). DM her something about it to show that you read it and thought it was interesting!
But, if you didn’t think it was interesting whatsoever, don’t pretend — girls can smell bullshit a mile away.
And don’t be that dude who responds to her latest Instagram photo via DM when you could have just commented. That shit is fucking annoying.
Let’s say the girl never follows you back, and therefore never reads your first DM, and now you’re stuck wondering if you’re ever going to get another shot.
There are a few other ways to get her attention, but you run the risk of looking like a stalker (especially if you’re not hot, because that’s how the world works).
As a blogger/writer who gets a lot of work through social media contacts, I have my email address in my bio. Occasionally, guys have sent me emails asking if I want to grab dinner/coffee/etc., and sometimes it has worked.
Obviously, this is very precarious territory because if a girl has her email in her bio for work opportunities, she might be pissed if you use it as a way to try to hit on her. But, at least for girls like me, it’s an easier way to get her attention rather than via DMs — plus it gives you a chance to write more and somehow seems less creepy than a DM (although it depends on who you ask).
If you’re going to attempt this route, you need to write a legit email, don’t type like you’re still in the DMs. Open it with a greeting, sign off, use full sentences, etc. Take advantage of the medium and write at least a paragraph or two explaining why you think she’s cool/interesting/etc. Also, if you’re asking her out, come armed with a plan (eg: I noticed you’re a big fan of donuts and I’d love to take you to this awesome new donut shop downtown) rather than saying something vague about how you’d like to “hang out sometime.”
I hope these tips help! If you have other questions, feel free to comment or message me!