How to Win Internet Friends (and Possibly Influence People)

genuine DMing for the socially anxious

The past month, I went from being an anxious buffoon who didn’t know how to make internet friends to someone who’s hung out with awesome people I genuinely admire. I’ve successfully secured a Substack cross-promotion and gotten future collaborators, all while keeping my soul intact.

This happened as a result of my stubborn determination to improve at the art of the DM. I’ve written this guide to help you do the same.

1.) START WITH GENUINE THOUGHTFULNESS AND APPRECIATION

You can start a connection by having immaculate reply game, tweeting something funny or smart as someone’s tweet is taking off. I currently suck at this, but there are other ways to initiate connections.

One approach I learned from my friend

Kasra

is to start with genuine appreciation. Kasra sent me this opening DM the day after I followed him:

This compact message that conveys he’s someone who’s actually read some of my essays and loves them. Compare that to a message from someone cold DMing a bunch of impersonal messages promoting their cohort-based course or startup. Who am I more likely to excited about hanging with in the future?

Here’s an example of a successful DM I sent to Monica Lim recently following Kasra’s example:

I’ve sent around 15 of customized appreciations in the past few months. Here’s what I personally enjoy about them:

• I’m not asking for or expecting anything in return, so I don’t feel as anxious about rejection.

• People generally don’t get heartfelt appreciation, so I’m not worried about getting classified as a spammer.

2.) DON’T TAKE NON-RESPONSES PERSONALLY

I’ve sent a few DMs to people with large followings. Sometimes I don’t get a response. I try not to take it personally, but I’m sensitive, and a non-response can sting!

Here’s how I currently relate to that.:

In general, the higher the follower count, the busier people are.

I have roughly 4000 followers on Twitter, so I don’t get that many cold DMs. As is though, I sometimes struggle to respond to everyone because I have a demanding job and a lot of anxiety (which takes time to sit with LOL). Imagine if I had 40k or 80k followers, my DMs would be a complete wreck. I try to keep this in mind when I message people with higher follower counts.

Send more DMs dammit!

I went to New York recently. To practice putting myself out there, I messaged three people who follow me on Twitter but who I consider “out of my league.” Not one responded.

I was upset, but then I remembered some basic statistics: If 10% of people can make time for a stranger, then you should message at least ten people to have a decent chance of 1 responding.

For some additional perspective, a successful startup friend who’s gotten success with cold messages tells me that out of 100 people, at least ten will respond. Think on the order of tens when it comes to cold DMs, not on the order of one, two, or three.

People not getting back to you in the future? Consider casting a wider net.

3.) BUILD BI-DIRECTIONAL RELATIONSHIPS

Can you ask internet friends for favors? I actually think it can be good to make requests of people, and learning how to ask for help is a huge growth edge for me this year.

twitter.com/kasratweets/status/1733996714275569666

Requests can be a gateway to deeper connection and vulnerability. I learned this when I was promoting an essay I’d written about my relationship to my father, a very vulnerable piece that touched on abuse. I asked many people to read and retweet my essay. The people who agreed often told me about their relationships to parents and/or asked me to read their writing in return. I’m pretty sure I never would have heard of their experiences otherwise — people don’t typically talk about abuse.

I’ve found that making requests can make others feel more comfortable making requests of me as well. After asking others to read my essay about my father, some asked me to give feedback on theirs. This was a win-win for me: I got to express my gratitude for their thoughtfulness and time.

It’s important to build a bi-directional relationship. As I ask for more help and end up receiving more help, I’m also going in the other direction and giving generously. I don’t want to be someone who simply takes. It feels bad, and also prevents a relationship from deepening even more. With mentors, even if the particular relationship might be more one-sided, I’m also looking for ways I can show them my appreciation or pay it forward.

I think Tasshin Fogleman gives really good concrete advice:

• Aim for at least 6 to 8 meaningful interactions per request you make

• Aim for a building a genuine relationship

• Try to make calibrated asks that are respectful of people’s energy and time

4.) BE YOURSELF RELENTLESSLY

Do you want to be liked for a fake version of yourself, or the genuine you? The former might get you short term gains, but only the latter is truly sustainable. I often feel insecure being myself (too much caps lock, too unhinged to be popular), and this means I often make myself more “normal” and “agreeable” than I actually am.

This often doesn’t work in the long-term. Why? Either the mask slips and you end up revealing your true self, or you suppress your authenticity at the expense of your soul. Recall the god-tier Disney movie Mulan. Mulan pretended to be a dainty, poised woman ready to get married off and simply couldn’t keep up the facade for even two hours. Now, maybe more skilled people could keep up a facade for longer, but can you imagine Mulan getting married off to a man she disliked and not saving China from the Huns? It would’ve been disastrous.

On a more serious note, I’m trying to lean into authenticity these days, even if it means risking being disliked. This means telling people if I find what they’re saying is rude and being willing to be as unhinged or serious as I feel in the moment.

5.) PLAY THE LONG GAME

Over the summer, I planned a birthday hangout and sent out the invite to a bunch of Austin group chats, filled with people I didn’t know too well. After a few days, only two people were going to attend (one of which was my roommate, so he doesn’t really count), and I felt pretty devastated. I showed the invite to my boyfriend Alex one night, and he said: “Valerie, this is a very sweet invite, but if I didn’t know you well, I probably wouldn’t want to attend.”

Cringe!

Alex was right: By mentioning presents, I probably made people feel uncomfortable. I also didn’t mention that people who didn’t know me were welcome to come. Looking back on the invite now, I kind of want to cringe.

However, this taught me a life-long lesson about the long game. Inevitably, you will get ghosted or you yourself will drop the ball on responding to someone’s messages. Inevitably, you’ll ask a friend for a favor, and you will get rejected, or you’ll second guess yourself if someone sends you a message you don’t know how to respond to. If you’re anything like me, these moments might make you question yourself, but it’s important to keep in mind that skills sometimes take years to develop and refine.

I’m still learning how to be myself and cultivate meaningful relationships with others. But at least now I know how to get more than two people to show up to my events!

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If I had to distill this post, it’s as follows: Be kind. Be bold. Be generous. Be authentic.

And be patient.

I’m still learning how to do this, but here are three concrete actions that helped me improve:

1. Beef up your public profile. Monica mentioned to me that she looked at my tweets after I sent her a DM. This is something I do too after people cold DM me. Tweet some bangers that show your personality and interests. 

2. Read How to Win Friends and Influence People by Dale Carnegie, which inspired me to write this post. It’s a funny read that provides a basic yet profound primer for relating to others.

3. DM a few people who you don’t know yet to express genuine appreciation for their content and perspectives. Watch what unfolds.

Thanks for reading! Let me know your thoughts in the comments below or cold DM me on Twitter ;)

If you enjoyed this essay, check out two related essays: How I grew My Twitter Following by 20% in Six Weeks and Seven Commandments of the Chill Hustler.

Thanks to Alex, Tasshin, Monica, Kasra,

Paul Millerd

,

Jason Levin

,

Kristin Posehn

, Dillon Shipper, and Reed Loustalot for their feedback. Thanks to Andrew Pynch for the Dale Carnegie rec.