How *Not* to Slide Into Someone’s DMs

With examples!

Ebony-Renee Baker
Illustration of a broken heart in a notification pop-up
(Illustration: Joel Louzado)

If you haven’t realized it yet, the days of pick-up lines are over. Instead of using cheesy sayings to attract romantic prospects IRL, the new cuffing tactic is the DM—i.e., the direct message. Yes, everyone’s on dating apps, but sliding into someone’s DMs has not only become a well-known meme, it’s an *actual* way people are meeting new partners.

But, just like pick-up lines, there are right ways to slide into the DMs… and very wrong ways. Laura Bilotta, a Toronto-based dating coach, helps people with literally every aspect of dating, from how to approach a person to creating your dating profile, so naturally, she knows a lot about what goes down in the DM. According to Bilotta, it’s totally possible to meet someone this way. “But it’s all in the way that you approach it,” she says. “If you do it in a tasteful way, then there’s nothing wrong with it.”

Unfortunately, there doesn’t seem to be an abundance of tasteful DMs. Proof: We asked six millennial women for screenshots of their most ~memorable~ DMs and, well, just read them below. We also had Bilotta critique each message. Hilarious? Absolutely. But she also offered up some v. helpful do’s and don’ts. Here’s her best advice for starting a convo in your crush’s DMs.

DM Don’ts

The Emoji Overload

An Instagram DM with three different replies to someone's story. Each reply is just lines of heart-eye emojis, kissing emojis and the "okay" sign

“You’re coming on too strong—sit down. It’s called *sliding* into someone’s DMs, [which means] doing it in a nonchalant way.”

The Money Offer

A caption that reads, "Hello, I stumbled upon your profile and I found out you are so beautiful, I'm ready to spoil you with all I have hun, I'm not here for anything sexual or a relationship. I'm a rich man and I choose to do whatever you want, I'll be giving you allowance of $500 everyweek [sic] hun. If you are interested just let me know ok?"

“Obviously, if you’re doing this, you’re not really being serious about a relationship because now it’s based on someone liking you for money. And you’re pretty much paying for something, so you get what you pay for. If there’s a girl willing to accept money for that, then that’s their prerogative.”

The Creeper

A DM that says, "Hi there. You don't know me! But I found your profile on tinder and haaaaadddd to talk to you. you are FUCKING gorgeous.... like god damn it can you take a bad photo? It's crazy...."

“Stranger danger! This sounds kind of stalker-ish. If I didn’t like you on Tinder, I’m not going to like you here. Leave me alone, buddy.”

The Persistent DMer

A screenshot of a person's replies to someone else's stories. Each message was sent months apart and the recipient never replied.

“Listen. What you should do is start liking and commenting on the person’s [posts] first. Don’t go overboard, but let them know over a period of a month or so that you’re interested. And then when something appears on their feed that you see an interest in then maybe message them directly and say, for example, ‘Oh I noticed you’ve just been to France lately, I was there last year.’ If you message them and they don’t respond, sometimes a popular person will get a lot of messages, so it’s OK to send something twice. If they don’t answer the second time, then you’re done.”

The Super Sexual DM

A screenshot of a DM that says, "I would love to give you a compliment and call you beautiful but beauty is in the inside and I haven't been in you... yet."

“That’s just a really cheesy, disgusting line. It’s gross. You’re being crude and rude. You might as well just send a dick pic if you’re going to do that.”

The Deep Question

A screen shot of a DM that says, "Dude i don't wanna slide in your DM's but I gotta ask like what's your take on existential crises? Like how to people consistently freak out over this shit [...] Feel like you're a good person to have a deep chat with"

“This is something you would do more on a post rather than a DM. Our attention spans nowadays have gotten really short, so a person is not going to sit there and respond to something deep when they don’t know you. But if you comment something on their post, that might strike something up.”

The (Literal) Cat Call

A screenshot of a DM that says, "Meowwwwwww" and a cat emoji

“Intrusive! It reminds me of construction workers, [you know when] you walk by a construction worker you can’t get by them without them whistling or doing something? It’s just very sexual. And you don’t want to be sexual.”

DM Do’s

The Genuine Q

A screenshot of a DM conversation between two people discussing whether they had gone to the same high school.

“See! Just be genuine and be you. There’s a greater chance of people responding to you when you’re yourself. As long as that isn’t crass and gross (then don’t be you).” [Editor’s note: A woman sent this to a dude she had just started following—and now they’re dating.]

The Friendly DM

A screenshot of a DM conversation between two women who are attending the same event

“This is great. I love that. Sometimes it’s easier to do when it’s two women or two men because there’s not so much of that ‘stranger danger’ there. Especially if you have a lot of mutual friends, I think there’s nothing wrong with it.” [Editor’s note: This is how two women became friends on Twitter. One woman replied to the other woman’s tweet as a direct message.]

Related:

Ask AnnieThing: Guys Keep Saying Awful Things to Me, Should I Just Give Up Dating?
Why Ghosting Is a Form of Self-Protection for Women
We’re Calling It: These are The Best (and Worst) Dating Apps

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