TL;DR: Do your homework. Have a clear, simple ask. Start with a clear reference or common ground when possible. Respect boundaries.
Growing up in the social media world, we’ve both been in the DM-er and the DM-d category. We’ve made mistakes, and we’ve also been annoyed in one way or another. That experience led us here, to writing this collaborative guide on how to DM someone.
This guide is for anyone who wants to DM thoughtfully on Telegram, whether you want to strike conversations with someone or simply have one question you want answered. In this guide, we’ll walk you through the pre-DM research and friendliness you should consider establishing first, how to create a good first impression, and how (if both parties are willing) you can continue the discussion.
Build public familiarity first (when possible): Talk to them in public group chats or, if they have a channel, in their channel group chats. If possible, you can also raise your discussion point here and talk with them without the extra strain of going to their DMs (and if your question is something along the lines of “how to get into web development?”, chances of you getting a good answer here without annoying the other person are better than DM-ing them).
Note: Don’t forget the existence of Channel DMs for Telegram channel owners. More often than not, you can easily get your answers through them than by directly DM-ing the owners. Use them properly.
Manage your expectations: In most cases, just because the a person is interactive online doesn’t mean they’re obligated to give you immediate answers or act exactly like the person they are in public. Understand that the persona people show in online platforms is a part of them, and not the whole picture of who they are.
Find a common ground: For example, for me (Eldad), the chances of you getting a warmer and better answer as someone who went to high school with me are better than someone who I interacted with at one event. Finding a common ground usually smooths interactions and leads to a better understanding from both sides.
Have a specific ask, topic or insight before you begin:
We (the writers) usually get a lot of “Hey, can we chat?” or “Hey, how are you?” DMs that usually get ignored, so do have something good to say when you DM. For the people that are DM-friendly, the least you can do for them is give them a concise, useful reason to reply.
Get straight to the point of what you want to talk about:
If you need to include a backstory, do a very short version of it that is relevant to the story. Don’t tell people your life stories to finally ask to choose between Flutter or Kotlin.
Lead with a reference or context:
If you can reply to a specific message, link to a specific link, or refer to a specific common ground, it makes it easier to answer back (people won’t have to search up what you’re asking) in an engaging way. Don’t expect people to suddenly remember who you are based on your ambiguous profile name and empty profile picture. The more specific you are, the better the interaction will go.
Start the right way:
This is the most important point, your first two to three messages break or make your interaction when it comes to answering DMs. Let’s show examples here.
Don’t do these:
The one who tries to butter people up

Devastating flirting attempts

Asking to ask

Note: Check out dontasktoask.com. Simply ask.
Instead, do this:

Use this as reference if needed:
[Greetings] - [Reference point: 2 sentences max] - [Background: 2 sentences max] - [Specific ask: 1 sentence]
Stay Authentic
Throughout this process, make sure you are authentic and not getting out of your way to talk to someone. Believe it or not, inauthenticity is very easy to notice and flag. Don’t fake your way into the chats and beyond.
Punctuate well.
I.e., don’t be this guy:
