This article was originally posted on Medium.

I originally made the article title as a joke in my Twitter drafts. Then I started writing, and this happened. This article also secretly acts as a general guide on how to cold email / Tweet / DM any person, regardless of gender or field— enjoy!

So! You want to talk to a girl on the internet. Specifically, a girl in tech. Take for example, Chloe Condon.

As you’ve probably seen from her tweets, she doesn’t take kindly to people sending random heys and hellos to her inbox… especially from men. She’s a lady on the internet — it’s justified.

But, you still would like to have a conversation with her, and probably many other people on the internet. How can you spark up a good chatterino?

Lets start with the why, and then break each one down.

Why? 🔗

1. You’re interested in talking to her as an attempt to court her
2. You would like to get coffee with her and “pick her brain”
3. You really admire her and her work
4. You have a technical question
5. You’re looking for advice
6. Other

The Approach 🔗

Ok so now we’ve got the why’s out of the way, let’s break each one down and what you should say.

1. You’re interested in talking to her as an attempt to court her 🔗

STOP RIGHT THERE. It’s not going to happen. She’s in a loving, thriving, long term, monogamous relationship and she’s not interested in disrupting it. This will not be changing anytime soon. Your attempts will be shut down and will be called out publicly.

Randomly messaging people you don’t know to ask them on a date generally doesn’t work. Every girl I know is creeped out when this happens. Regardless if single, messaging a stranger on the Internet to ask them out on a date is creepy and not welcomed (unless you’re on a dating app, where this action is fully acceptable).

Please read the situation carefully. If the woman is obviously posting about her long term boyfriend on a regular basis, she probably isn’t interested. If she’s publicly calling men out on her Twitter about their attempts to court her, probably don’t try either — you won’t be an anomaly.

Before someone comes back at me and says, “Oh, but I met my current significant other by randomly messaging them on Twitter!” That’s actually super cool. The Internet is amazing for connecting people. I’ve met my closest friends through online interactions. What’s important is learning and understanding how the person will react to your attempts. If she obviously has posted mocking tweets calling out men who try to ask her out via her DMs, you probably shouldn’t ask her. It’s simple. And don’t be like these guys. Be aware of how she will react. Don’t be surprised if she says no. Be understanding if she says no. She does not owe you anything for your attempts… or your Twitter likes.

Obviously, Chloe doesn’t know you. She doesn’t even know what you look like. Sorry, Twitter bio pictures don’t count. Don’t send her a picture of your dick either. She doesn’t want that. None of us want that.

2. The Coffee Chat 🔗

So — the coffee chat. You’re going to be in town, and would like to talk to Chloe. That’s awesome. Hopefully, she has time in her schedule to see you! But how do you ask?

Asking someone to coffee in order to “pick your brain” is an empty statement. If you don’t have your topic of choice lined up, it’ll lead to awkward silences and forced topics. As a heads up, Chloe will not show up with a pre-planned lecture to give you.

Instead, be clear about what you want to discuss. Additionally, this gives Chloe a heads-up to think about the topic a bit and maybe prepare some material (a few interesting links, a book to recommend).

Take, for example, this short and simple message stating who I am, what I’m looking for, and offering delicious coffee/boba in exchange for Chloe’s time:

Hey Chloe - I’m Ali! I am moving to the Bay Area next week from New York City and I’ll be working as a developer evangelist at a stealthy startup. I’ve been following you and your work on the Sentry Scouts meet ups (congrats on the award!), and am looking for some guidance on how to plan, carry out, and execute an amazing tech meet up. If you have some time next week, I’d love to talk to you over coffee (or boba) — my treat.

Also, keep in mind, there’s a chance she will say no. If she says no, say thank you, and move on. Badgering her to accept the coffee chat will not work.

Honestly, I’d highly recommend checking out Cassidy Williams’s article about the cold email. I learned a lot of this from her article.

3–6. Everything Else 🔗

The rest of them basically fall under the same approach.

You have a technical question. Or you’re looking for some advice. Or something else, like a burning question about her opinions on Sondheim’s influence on modern musical theatre. Amazing! Hopefully she’ll be able to help. The best way to start a conversation with her is to be clear and concise about your intent. Have substance to your message. Here’s a couple of examples:

Hey Chloe! I saw your post about Furby hacking — I, too, am a Furby hacker. I was wondering where the documentation lists the commands for the Do-Re-Mi scale? I can’t find it anywhere!

Hey Chloe! I recently graduated from a tech boot camp, and was thinking about pursuing developer evangelism. I currently only have an offer to be a front end developer, but am in the pipeline for a few developer evangelism positions. I was wondering if you could give me some advice on how I can secure those developer evangelism offers?

Hey Chloe, I saw your promotion for ModCloth. I was wondering what is your favorite piece from ModCloth? I’m interested in buying something for my friend and she has similar style to you!

Chloe — great job on your keynote at DjangoCon. I just saw it and thought it was really well presented. Thanks for the enlightening talk!

Hi Chloe — I recently watched your talk from DockerConEU 2017. As I was watching you mentioned the phrase “Docker is not a virtualization technology, it’s an application delivery technology.” I was wondering if you could possibly elaborate on that point a bit more? It left me a bit confused!

Note that each of these examples have substance to them. The motivation behind your message is clear and upfront. Chloe is not left to guessing what your random hey means.

If she’s made a mistake somewhere, don’t go into her DMs or replies, guns blazing, telling her she’s wrong and that she’s less than you. A great way to strike up a conversation about a potential error is seen in last example, the Docker presentation discussion. That cold message is a great way to be see her understanding of the material, and understand her familiarity. Be tactful with your corrections and be understanding of her abilities. Chloe isn’t perfect. No one is — except Beyoncé. Find the right time in the conversation to say:

From my understanding, I found the contrary. Here’s a source from where I learned it. What do you think?

This is a great way to back up your statement, without being rude and sounding entitled.

Closing Statements 🔗

Chloe doesn’t owe you anything nor does she owe you a response. She will respond when she can — if she can. If she can help you, she will try her best. If she can’t help you, she’ll let you know and maybe point you to someone else or a good resource. She’s trying her best, and remember, she’s a human.

As a heads up, harassing someone on the internet, and then calling it a “social experiment” to cover your tail doesn’t work. Be respectful, and think, “would it be okay for me to talk to my mom like this?” If the answer is no — don’t do it.

Whether you are trying to talk to Chloe, any other girl, or person on the internet be clear and concise with your reason for discussion up front. It helps clarify your motivation much more than a hey does, and it gets the recipient excited to talk to you. Who knows, maybe you strike up a conversation with Chloe and actually become friends IRL!

Consider these rules as a good guideline — not as perfect gospel. Some things that work for one person may not be okay for another.

Thanks for coming to my TED Talk 🔗

PS: Chloe doesn’t work in cryptocurrency, she never worked in cryptocurrency, if she wanted to work in cryptocurrency, yes, she probably could go out and get a job in cryptocurrency because she is what? Sickening. She doesn’t want to work in cryptocurrency because she is not that kind of girl (for now). Baby, everything she has she has worked for and she got herself. She built herself from the ground up…

Thank you to Chloe Condon for reviewing this article.