How to Slide into Someone’s DMs Without Embarrassing Yourself

Direct messages (or DMs) are a fairly low-pressure way to take conversations over social media to a more private place. But just because it’s easy to initiate a private chat, doesn’t mean the interaction isn’t riddled with obstacles and pitfalls. Not only do you have to grab someone’s attention immediately, but you don’t want to offend or turn them off with an ill-received joke or aggressive behavior.

We talked to relationship therapists, sex experts, and love coaches and asked them to give us their best, most sensible advice about sliding into someone’s DMs: what to say, how to say it, and when to make a move. Here’s what they said. Answers have been edited for length and clarity.

Subtext Matters

Just like there is a subtext if you’re using Tinder (that you are most likely looking for something casual) and there is a subtext when you’re using Match (that you are looking for something serious, even marriage), if you are DMing someone, the subtext is usually in the Tinder category, i.e. you’re looking for something very casual. If that is not your intention, then you need to make that clear from the start if you want to have a positive interaction and avoid hurt feelings.

Don’t be a creep. If most or all your DMs result in getting blocked, you should probably stop. If you are looking for a serious relationship, DMing is almost always a terrible idea. – Sean Jameson, Founder of the Bad Girls Bible sex advice site and podcast

Just Do It, But Don’t Be Too Cool

People put far too much energy into thinking about what phrase to write, picture to send or video to share. There is no perfect DM so don’t bother trying to create one. The bottom line is that if someone is interested in you, they will be open to whatever you send.

You may think that it’s better not to show too much interest and to let DMs linger unanswered. You may think that you are creating some tension and mystery in the interaction, but really, all you are creating is anxiety. People don’t like not being responded to and they start to feel insecure. – Rhonda Milrad, relationship therapist and founder of online relationship community RelationUp

Hold the Compliments

Most people message with generic compliments about the other person’s physical appearance. Since this is how so many people try to approach first messages, they don’t ever stand out. Worse, you can come off desperate because you’re just like every other person who’s only enamored by someone’s appearance and not who they actually are.

When you write a message that includes some context for why you reached out, then the conversation feels organic. Maybe they posted about surfing and you want to share your passion for it since you’ve been surfing for ten years. Or you could even just joke about how they looked like a natural elephant tamer on their recent trip to Thailand. Again, have something more to say than “Hey, you’re so cute.” – Nick Notas, dating and confidence consultant

Don’t Be Boring

Don’t just say “hi.” The point is to break the ice and start a conversation. “Hi” doesn’t do that. Hi is like poking someone. You are delaying the actual conversation. “Hi” is a throwaway. Same goes for “What’s up,” “You’re hot,” or “Thanks for accepting my friend request.”

Instead, comment on and ask a question about something in their profile. Even better if it’s something that you can relate to and can bring yourself into within that first outreach. Be careful with jokes and sarcasm. Humor can be hard to capture over text. Sarcasm will more likely come across as mean. – Laurel House, Celebrity Dating Coach and Resident Sex Expert for My First Blush

Take the Conversation Offline ASAP

Ultimately, you’ll know if you connect or not by meeting face-to-face. If there is context you can use to move offline, that’s ideal. For example, if you’re talking about a new restaurant or art exhibit, you might go experience that together. And if there isn’t natural context, it can be as simple as stating your desire like, “I love DMing with you. It would be fun to chat in person over a cocktail.” – Laurie Davis Edwards, love coach and founder of The Worthy One

Sign up for our newsletter to get the best of VICE delivered to your inbox daily.

Follow Anna Goldfarb on Twitter.