10 Tips for Sliding Into His DMs

There’s this guy you can’t stop thinking about. Maybe you met him at the gym or in a class. Perhaps you’ve seen him at the store or maybe at a friend’s party. Just your luck, you two met, chatted, and chemistry was felt when you had your first chance encounter with him. You had such a good time together that you exchanged information. Which, in 2020, means you became friends on your social media channels.

Unfortunately for you, getting this guy outta your head is proving more difficult than not. You want to approach him or at least ask him out on a date, but will it be weird? Are you crossing boundaries by asking him out? Where and how do you even begin to approach somebody that you think is smoking hot, that might also be interested in you?

It’s no longer about calling or texting anymore. These days, you’ve got to make your way into his direct messages as the best way to connect with a stranger you just met—or haven’t even spoken to yet. Whether the two of you have met or not, properly sliding into a dude’s DMs can be tricky, so knowing how to navigate DMing a virtual stranger is essential for a successful connection. Here are 10 tips for sliding into his DMs.

1. Find out what he likes.

While I do not encourage stalking and internet trolling just to pick up a guy, it doesn’t hurt to also do your preliminary research. After all, you are now friends on social media. So do a little snooping. Or wait until he posts, but that could be a while before you gain any pertinent information about him. You could also ask mutual friends or acquaintances that you both have him in common. 

Figuring out his interests can lead you on a direct path of having something deliberate to talk to when sliding into his DMs. You’ll have a reason and a subject to talk about, versus just hitting him up out of the blue.

2. Don’t be a catfish. 

Sure, nothing online is really as it seems in real life. But you want to put your best real foot forward. Don’t shy away or hide who you are. Be true to yourself and the guy when hitting him up. It’s one thing to embellish, it’s completely another thing pretending to be something you are not. Both of you deserve honesty, and you’re setting yourself up for imminent failure if you embellish or make yourself out to be something completely different than you truly are.

3. Come up with a game plan. 

What are you looking for by connecting with this guy? Be real with yourself and come clean as to what your expectations are. If you want a relationship, acknowledge that to yourself. If it’s just sex, that’s fine too. Whatever you are looking for, just be honest with him and you. Having an idea of what you’re looking for will prepare you for whatever he is willing to get into with you. 

Having this basic game plan of knowing what you’re looking for and how you might go about getting it allows you to operate with a purpose versus aimlessly just trying to wing it with DMing a guy.

4. But don’t overthink it. 

This isn’t Sherlock Holmes and the Case of the Missing DM. All you are doing is direct messaging someone you are interested in. While you need to exercise caution, the best advice anyone can give you is to just be yourself. Don’t make yourself crazy wondering what would be the most appropriate or funniest thing to say to win him over and grab his attention. Keep it simple, sweet, to the point, and matter-of-fact. 

Don’t let your message get muddled by over-doing it. If you’re still stumbling for what to say, ask a friend for help. There’s nothing wrong with asking for help when it comes to advice on knowing what to say to a guy and when.

5. Remember that his direct messages are not equivalent to Grindr. 

Gay guys have a notoriously bad habit of laying all their cards on the table before a proper hand has even been dealt. Save your hole and dick pics for when he asks you for full nudes later on down the line. A good friend of mine once told me: “The more clothes you have on, the sexier it is because it leaves your lover’s imagination to undress you.” Use this same thought process with him: leave him longing something other than him wishing you’d never sent a nude pic he never asked for.

Put on your gentleman hat, have some manners, and respect the fact that no one likes unsolicited pictures or comments. It’s harassment if you do and he isn’t into it or no consent was given.

6. Figure out if he is really into you or not. 

If you sent him a friend request he didn’t respond to or if he doesn’t follow you back, he might not be as interested as he seemed upon first meeting. Though not completely indicative of his mindset or feelings, a great way to see if he is feeling you or not is by liking or commenting on ONE post. Maybe two spread out over some time. You don’t want to come off as needy or too 'creeperlicious.' 

And you most certainly don’t want to waste your time fretting over a guy who may or may not even be into you in the first place. You can again ask around to see if he is interested or you can wait to see how he responds to your likes or comments, and go from there.

7. Once you’re in, stay in by playing it cool and coy. 

Relationships and hookups shouldn’t be a lot of work, and if he gets a whiff of any drama or crazy early on, he mightn’t want anything to do with you in an attempt to simply avoid stress. You don’t have to downplay who you are, but maybe keep some personal, negative, or dramatic things to yourself for a while before divulging all your secrets. Don’t overwhelm him with too many messages, either. 

Casually reaching out is enough, and if he responds to your subtle advances, you can proceed accordingly. Wait until you get into any of the heavy stuff when you guys are one on one and physically hanging out.

8. Don’t be sloppy. 

SO much can get lost through digital messaging versus voice to voice connection. Use spell check, proofread and edit, and make sure your message sounds right and reads well before pushing the send button. Otherwise, you’ll end up feeling like you have to send an additional message of clarification, and that just looks messy. Be conscious of the way you would want someone to slide into your DMs and try to use those same manners as you would want to be treated.

Sloppy equals messy and messy isn’t someone anyone wants to date nor takes seriously. Dot your i’s, cross your t’s, and make sure you step off on the wrong foot with this guy right out of the gate with a silly error or misconstrued message.

9. Have patience. 

Not everyone is always digitally connected to the world, and not everyone is able to respond to something in a timely manner you prefer. Most people need time to process messages and conversations before offering a comment. Once you slide into his DMs, give him the time and space he may need in order to give you a proper adult answer back. You deserve to have his full attention when he is talking to you, so wait until he is ready and not surrounded by distractions to make the second move and message you back. 

If he ignores you altogether or takes days or weeks on end to respond, just realize that he isn’t in a place where he is able to reciprocate the same energy you are putting out.

10. Go into it with a positive mind and open heart. 

You aren’t setting yourself up to fail if you don’t have too many upfront emotions or expectations sliding into his DMs. For all you know, he could be the man of your dreams, and by playing it upbeat and cool, you attracted him more by being a new light in his life. Or, maybe you guys won’t work out at all romantically, and instead, find a plutonic pond between the two of you. You don’t know this guy, so it’s useless to pick out wedding china and adding his last name to yours before anything has really gotten started. 

They say that you will find love when you least expect it and when you aren’t looking for it. The more organic, raw, and real you are with a person and situation, the more likely you are to attract that kind of outcome and result for yourself.