I’ve earned a reputation for being an assertive, direct person when it comes to letting someone know that I’m interested, romantically or sexually. What I haven’t talked about much is that many of those “hey, I want to bone you” conversations have happened over text message, when I couldn’t see the person’s face and they couldn’t see mine. Words make me bold, make me stronger, and hitting on someone through them is worlds easier than telling them in person. And rejection, when it comes, is much less painful to process when it’s letters on a screen.
Weirdly enough, I often find myself enjoying the banter and nervous expectation of texting more than the first date itself. It’s a battle of wits, even as I’m comfortable in my pajama pants watching Netflix. Texting is also safer, both physically and emotionally—I can suss out my buddy’s intentions from the security of my own home, and if an interaction goes wrong, I am miles away from them.
But how do you come up with that brilliant, pithy line or comeback? How should you ask someone out and be both funny and totally chill? My friends send me screenshots of their text conversations all the time with the message “WHAT DO I SAY TO THAT?” So by popular demand, here are some of my unorganized thoughts on being a boss at texting. It is not comprehensive but it’s a start.
Texting 101:
1. You’re going to need a better opening line than, “Hi.” This goes double on any sort of dating app or website. If you open any lady’s OKCupid inbox, it is literally an endless list of heys, hi, what’s up, hiyah 😉 and hello.
2. Someone asks you what you’re up to? Don’t say “Not much.” You’re clearly doing something, whether it’s watching Netflix or building an IKEA bookshelf or scowling at the fan you think your roommate broke while you were out of town. You don’t have to be doing something impressive in order to be interesting. And if someone asks you what you’re up to or how you’re doing and you give them a non-answer, what incentive do they have to keep doing all the work to move the conversation forward?
3. Ask questions. Seriously, if you’re texting someone who you’re still getting to know and a topic is drying out, just ask them who they are. What’s their favorite TV show? What’s their favorite cereal? Do they have siblings? What are their feelings on roller disco? People like to talk about themselves and you might discover new things in common. They will also feel heard, and that’s huge.
4. Stumped? Crowd-source your texts. I get called in at least twice a week to help a friend write a text to the girl or guy she’s crushing on. Someone with no stake in the relationship is less likely to worry about getting rejected and can help you put together a clever comeback or semi-aggressive flirtation. They might also offer some perspective on whether or not this person actually seems into you.
5. Emoji are for the weak. Ration your usage of winky faces, smiley faces, etc. Please use your words, as this is not kindergarten.
6. Don’t do any backhanded half-compliment shit. You will get nothing from being patronizing or aloof. Never express surprise that you’re clicking with someone if it implies there’s a reason you wouldn’t be. I’m guilty of being condescending when I’m feeling insecure, and a bro skillfully called me out on being an asshole when I commented on how interesting he was. “What, did you think I was some dumb jock who only cares about protein powder?” Well, yes, I did. Because I was an asshole.
7. Are you making plans? Suggest things! Get your ass on Yelp and find a cool café. Look up some movie times. Take initiative and be thoughtful but flexible. “There’s a concert tonight at Sidewalk, but I’m down for whatever,” is a good way to offer an opening to someone who probably also has no idea what to do.
8. If you’re inviting someone over to your apartment, maybe to watch a movie or because you want to cook them your signature pasta dish, that is a sex thing. That is the implication. In case you didn’t already know.
9. Make your intentions clear. I’m a HUGE fan of being gently assertive: letting my interest be known but not in a way that demands anything of my texting buddy. Getting that right is a delicate balancing act and can take a while to master—I don’t have any magic wand advice as to how to nail it. It involves a dash of making yourself vulnerable while showing them that you are hella strong and wouldn’t be upset by a rejection. Feel free to invent clever variations on this basic template: “I’m happy we’re becoming friends because you’re awesome. But to be honest I’m interested in being more than that—how do you feel?”
10. It’s okay to ask for clarification. One of my all time favorite lines is, “You’re cute. I never know what to make of you.” It says EVERYTHING: I’m interested in you, I have no idea if you’re interested in me, and this is exciting but please give me something to work with. And it’s so SIMPLE. You are welcome to steal it.
11. If someone has just asked you for clarification, give it to them! Don’t lead them on or toy with them if you know it’s not going to happen. If someone is coming onto you strong and you’re not into it, you definitely should bail as soon as possible. If you don’t know how you feel about them yet, you’re allowed to say that too. Explain that you’re still getting to know them, or you aren’t sure what you want right now, which are shitty options to hear but are necessary if they’re the truth. And fuck, if you do like this person, why would you not want to tell them? Don’t make them sweat for no reason. HONESTY. HONESTY IS GREAT.
12. Don’t be a dickbag! Seriously, don’t be a dickbag. I trust you guys to figure out what that means for yourselves.
Advanced texting theory:
1. Are you terrible at communicating your thoughts or your personality in writing? Own up to it. There’s no shame in not being a wordsmith (or just being shy), but it can be helpful to give the person you’re texting a heads up so that they don’t get paranoid that you suddenly hate them… or that you’re way more boring than you seemed when he or she met you at that party.
2. No one is actually “bad at texting.” “I’m bad at texting” has three possible translations: “I am not actually interested in you but would prefer to blow you off rather than admit it”; “I am interested in you but you fall beneath work, family, friends, and various hobbies on my priority list, and I would rather interact with you at a time that is suitable to me”; and “I am a flake who is terrible at modern technology and will probably drive you insane.” At the end of the day, if someone wants to talk to you, they will find a way. If they’re not putting in a ton of effort, there is usually a reason. Which leads me to…
3. Pay attention to the ratio of texts you’re sending to texts you’re receiving. Not because it’s a power game and you want to be the more aloof one—if you’re both marathon texters who regularly send each other novels, by all means go ahead. But if someone is noticeably not reciprocating your enthusiasm, they might be too polite or scared to ask you to tone it down. Women often have trouble telling men to back off because we’re socialized to think the enthusiastic attention of a man is the ~end goal~ regardless of how much we actually like them. Also because calling someone out on their behavior can lead to them behaving like a violent, misogynistic dick. Meanwhile, dudes just like to ghost. Pretty much all the men I’ve dated will put off an awkward rejection conversation and just let me keep texting them for weeks. If someone isn’t putting in the same amount of effort, chances are their silence means something. Take it down a notch and see if they seek you out.
4. If at any point your texting buddy would like to stop texting because they’re at work or they’re with friends, stop texting them. Seriously. It doesn’t necessarily mean they no longer want to talk to you—people have actual lives and sometimes flirting needs to take a backseat for a few hours, or even days. As a social media manager, I need to use my iPhone at the office all the time to work on mobile platforms like Instagram and Snapchat. Getting a bunch of texts while I’m trying to share an Instagram post with 400k followers is not only annoying—it’s stressful. Sending me a bunch more texts to read later isn’t helpful. When someone says stop, stop.
5. Related: if someone tells you to never text them again, don’t text them again! That is what harassment is. If you keep texting someone who has told you never to text them again after they continue to ignore you, CONGRATULATIONS ON THE CONTINUED HARASSMENT.
6. What time is it? If it’s after midnight, you are texting someone because you are: a) drunk, b) horny, or c) emotionally needy. Let’s be real here. You know it. They know it. We all know it.
7. Screenshots are a thing. Be aware of this. I wouldn’t screenshot a personal confession someone has made and forward it to all of my friends—that’s fucked up and disrespectful. You wouldn’t post an emotional moment on Facebook in the same way you wouldn’t share a partner’s nudes. But if you’re being elusive, weird or offensive, I’m not above screenshotting our conversation and sending it to a friend to be like, “What the fuck?” And if you send me a million unwelcome text messages, you know I’m saving that in case I ever need evidence of you being a dangerous toolbag.
As always, you can find me on Twitter, where I live-tweet my texting with bros:
when bae doesn’t answer your text but has time to update his snapchat story pic.twitter.com/cJGQgOwM1v
— Ella Dawson (@brosandprose) May 20, 2015
Ella Dawson 
I love your practical advice blogs!