The Gay Man's Guide to First Texts

Welcome to the perilous, thrilling, and utterly overthought world of the first text—a place where the right emoji can feel like a love spell and a misplaced comma can seem like a deal-breaker.

Congratulations, you've snagged his number, probably after three too many drinks and a promise that you're not like other guys. But now, the real challenge begins: crafting that first message.

You're about to  learn about gay texting, the fine art of appearing interested without seeming desperate, witty without trying too hard, and mysterious without looking like you have something to hide (like your obsession with reality TV).

So, take a deep breath, put down that glass of wine (you've had enough), and prepare to dive into the digital dating dance. Whether you're aiming to be flirty, funny, or somewhere fabulously in between, this guide will ensure your first text is less 'seen at 11:57 p.m.' and more 'replied at 11:58 p.m.' Welcome to the minefield, gentlemen. Let's make some explosions!

1. Do NOT send an open-ended text. 

Take it from us, the gay dating advice experts, here’s the very worst one you can send:

“Hey, what’s up?”

You will just get the obvious, socially programmed response of "Not much, how bout you?" This is an interview question, and will bore the hell out of your crush.  In fact, you may as well have texted:

“Would you mind coming up with something interesting to say 
because I’m so boring the plaster peels off the wall when I talk to it.”

Not only are you announcing that you’ve got the personality of a Kansas zip code, you’re leaving his in the awkward situation of creating the value for a conversation you started.  If you start a text thread don’t ask for value; deliver it. Your goal shouldn’t be to start a conversation. It should be to bring a smile to his face.   The best way to do that is to learn how to…

Assume Rapport.

The ability to “assume rapport” is one of the most useful social skills you can have. It will literally open doors for you in dating, business and personal relationships.  Rapport is an emotional bond based on a shared understanding. The best way to get it is to pretend youʼve got it. Donʼt seek it; assume it. 

Rapport seekers fish for a connection by asking yawners like “Whatʼs new?” “What do you do?” and “Where are you from?” If youʼve ever been on the receiving end of those questions from somebody you don’t know--and aren’t sure you want to—it feels as if somebody’s checking your pockets to see if you’ve got change for a dollar. It’s way too invasive. Donʼt do it. Act as if you know him. Talk to him like you used to ditch class together.

People who have genuine rapport donʼt talk in meaningless questions. They talk in statement form or in meaningful questions.  Letʼs say youʼre at a grocery store and you spy a hottie:

Asking for rapport: [directly approaching his] “Hi. Iʼm Mike. Whatʼs your name?”

Assuming rapport: [holding the bottle and asking indirectly] “Whatʼs up with 1% milk? Is it really any better than 2%?”

What’s the difference between asking and assuming rapport?  Asking for it puts his guard up.  Assuming it lowers it.  Asking for rapport creates a try-hard energy.  Assuming rapport creates camaraderie.  How does this translate into texting?  Text as if you already know him. 

2.  Be quirky.  Be fun.  Be observational. 

Remember, the golden rule of getting laid:  He Who Makes Him Laugh Makes Him His.   Your job is to make him smile, to associate you with good times, a chuckle or a laugh.  Which text do you think a guy would rather get:

“Hi, how are you?”

Or

“I just saw a drag queen on a mini-scooter stop at a
 red light and fix his make-up. 

Can you beat that?”

Which text do you think would make him want to get to know you better?

“Sup.”

Or

Do you think naming two puppies Millie Vanilli is a little over the top?

Asking his opinion is one of the most effective ways of engaging him, especially if you do it with wit.  Don't be afraid to be a little off-the-wall.  It sets you apart from the rest of your tired bros.  Interest, smiles, and laughter--these are all values you want to bring to the table.  Now the truth is there’s nothing wrong with asking him how his day’s going as long as you’ve put the funny in it:

"My cell phone fell out of my shirt pocket while tying my shoe on an escalator....which was followed by me being accused of trying to sneak an upskirt photo and being violently shoved down the top of the escalator. How's YOUR day?"

Now THAT’s how you ask a guy about his day!  Remember, you can’t overtly flirt with someone who’s hesitant about you, so you have to create value—even in the ways you say hello.  You can also do it by engaging their curiosity. You could send a message like:


You:  You’ll never guess what happened to me last night!

Why it works: It hints at something funny or adventurous, and who doesn’t want to chuckle or hear something fun?  Even better, he’ll think you’re setting it up to say that you met this cool guy (him) last night.  So when you throw a curve ball at his expectations he’ll be more intrigued.  The challenge with this flirt idea is that you have to deliver on the promise. So get creative. Think of something funny that’s happened to you or just pretend it happened. Here’s an example:

Last night, my friend changed all my contacts in my phone. I have been texted by

Batman, Beyonce, and Harry Potter. WTF!

3.  Reinforce the memory of your interaction---with wit.  

Why make something up when you can use something comedians use all the time:  A “callback.”  The main point of a callback is to reinforce a sense of the familiar.  It “calls back” to an earlier joke in which the audience laughed.  Here’s an example in joke form:

Two men are sitting on the front porch of a small town hardware store. First guy says: "Man things have been tough; I haven't sold a tractor all month..." 



Second guy interrupts, saying: "You think you've got it bad... the other day I went out in the barn to milk the cow; darn thing kicked me right in the shins. So I tied his leg to the stall boards and moved the stool over to the other side. Then he kicked me with THAT leg; so I tied his other leg to the stall boards on that side. THEN he started swatting me with his tail, so I tied his tail up to the rafters.

If you can convince my wife I was gonna MILK that cow... I'll buy a tractor from you!" 



Notice the standard punch line (“If you can convince my wife I was gonna milk that cow”) is followed by a callback (the tractor). 

For texting purposes, a callback is a reference to something you talked about when you first met.  Let's say you were both bitching about your jobs when you last talked.  You could send a callback text like this:

“I swear, my boss is so conceited he takes a bow when he hears thunder!”

Or 

"My boss is doing the work of three men: Larry, Moe and Curly. Hope your day is

going better."

Or

"My boss has my hair on fire. You?"

The point is to make every email vibrate with a witty sheen that makes him want to know you better.  You can control whether texting breeds contempt or desire.  Give him a "Hi, how are you?" and you’ll remind him why he wasn't excited about giving you his number.  Make him smile and he’ll wonder what else there is to you.

Now What?

Alright dudes, let's address the neon pink elephant strutting across our gay dating app parade: Sh*t happens. Best intentions and witty text banter can't safeguard you against the ruthless ghosts that will inevitably haunt even the smoothest dating app hook ups.

But while ghosting stings and Mr. Amazing fizzling out after date #4 burns worse than an untreated STD, all is NOT lost! Just ask us - veteran waders of the treacherous gay dating pool. 

Armed with our expert gay dating tips, you can slay countless bad dates and semi-existent text convos until finally ensnaring your boo. But the first rule is ditching desperation (we smell that miles off, gentlemen) and standing confident in your worth.

You bring wit, warmth and wisdom to the table! Any dude ghosting that shining package is his loss! Which is why the endless sea of gay dating apps online can work in your favor. 

When you encounter ghosts, orbiters and bad texters: move along to a man who doesn't carry more baggage than a Kardashian on tour. With patience, an awesome profile and a few of Auntie's signature gay dating app pick up lines, you'll meet someone worth the hassle soon enough!