Dating > Texting > Masculine Texting
by Coach Calvin • Updated: July 1, 2023
See Also
How to Keep Interest Alive by Being Masculine Over Text
Today I’m gonna talk about one of the big problems in dating that is likely to end up making you lose the girl you want.
The problem is lack of masculinity in your texting.
One of my private coaching clients, Lyle, was dating this girl Allison, who he really wanted a future with. But he felt her slipping away. They had been dating about two months, but they hadn’t had sex in a month… and now she was barely replying to his texts. It had gotten so bad that she was starting to take a full day to reply to his texts.
Allison was out of town for a week to be a bridesmaid in a wedding, and since leaving on the trip, all she had done was send him a picture of her and her friends in their bridesmaid dresses, posing in front of a hotel. Just the picture, without even adding any writing. That’s a warning sign, because it’s a very low-investment text, meaning she didn’t put much effort into it.
So it was Lyle’s move now. He needed to reply to this photo in a way that got the attraction back on track, before she completely slipped away.
I looked through screenshots of his previous texts, the texts that Allison had taken a full day to reply to.
I said, ‘Here’s the problem with those texts. They’re passive and boring. They’re not contributing anything of value, you’re just asking her question after question, like you’re an empty shell hoping for her to bring something interesting into your life.”
He said, “I thought I was being nice.”
Now, when I work with clients, one of my favorite things to do is to learn about a guy’s life and find that one key revelation about his life that allows me to make all my lessons click for him.
Mistakeless and Flavorless Texts
Lyle plays in a successful band. While he was telling me about his life, he told me that the worst review he ever got was for his first album, where a music critic described his album as, “Mistakeless and flavorless.”
He says he never got over the sting of that review. The critic wrote, “Technically without error, this album is so caught up with playing it safe that it ends up making no impression at all. This is the most technically perfect, bland and vapid album I’ve ever heard. Do his good intentions count for something? Maybe. Do I want to listen? Absolutely not.”
Lyle told me that this review had basically been haunting him for years, and motivated him to take more risks in his music.
So now, as I was reading through his texts to Allisoni that said, “How’s your trip going?” and “Hope you’re having a good time,” I said, “Don’t you see? What that critic observed in your music ten years ago wasn’t the problem. It was a symptom of a problem. The problem is the underlying mentality you developed as a kid, probably because your parents overcriticized you. You’ve got this constant fear of anyone finding fault in you, so you get preemptively scared, and before anyone criticizes you, and you rush to sanitize yourself so that you can’t possibly be offensive to anyone. You did it in your music ten years ago, and you’re doing it in your texts now. You’re so concerned with not rocking the boat that you end up with texts that have nothing memorable about them at all.
I asked him, “What was your best idea to reply to that picture from the wedding that Allison sent you?”
He told his ideas:
“Maybe I’ll say ‘Nice picture.’ It would be rude if I don’t tell her I like it. Or maybe I’ll write, ‘Hope you’re having a good time.’” or “How is everything going?”
I said, no, man, that’s the same ‘mistakeless and flavorless’ mentality that ruined your first album. You need to steer this conversation in an interesting direction. Infuse something entertaining into it. Have a personality, have a point of view.
He said, “I’m so used to making sure I don’t have an offensive point of view… I’m not sure I even know what to have a point of view about.”
I said I can work with that. Let’s make a list of all the things you could potentially text about.
I asked him what he knew about Allison’s trip.
He said, “The bride lives in Sweden and she’s getting married to this Swedish guy. They’re having the wedding in the U.S. because, it’s sort of a scandalous thing… the groom was married before and they were having an affair and there was some concern to keep the wedding a secret over here in the States so that his ex-wife wouldn’t be tempted to show up and do something crazy.”
I said, “So you’re telling me… you have THAT incredible story available to be texting about… and all you could come up with was, “Hope you’re having a good trip”?
If you have subject matter like THIS to pull from, you’ve GOT to be playing up the saliciousness of it!
Women feel a magnetic pull towards a guy who writes EDGY texts.
Edgy means being a little bit rough around the edges. A little bit mischievous. For no other reason than to keep yourself entertained. And it’s masculine because you’re marching to the beat of your own drum, not worried about anyone’s opinions.
I wrote this text for him to send:
Now I knew that text would be good. But Lyle wasn’t so sure. He said, “How about instead we change it to, ‘‘Hope the wedding didn’t draw too much attention”?
I said, “See, Lyle, that idea is a lot more general. General is always less interesting. Specific is always more interesting. With the text I wrote, Allison will get a specific image in her mind of some crazy Swedish lady bursting in and getting pushed into a pool. With that text you suggested, Allison won’t get any image in her mind. That’s why she’ll ignore it or take forever to write back.”
Once I convinced him of that, he got even more nervous because that meant he would have to actually send it. And he started coming up with more reasons to doubt the text.
He said, “Well, I don’t want it to end up that maybe I remembered wrong about the story of the groom’s ex-wife in Sweden. What if I’m remembering that wrong and the text makes no sense, what if she gets mad at me for remembering wrong?”
I said, “Lyle… I don’t think you could remember something that incorrectly. I think your mind is just going into a defense mechanism to get you to doubt yourself because you’re so scared of offending her with an edgy text. Trust yourself more. If you think that’s the story she told you, that’s probably the story she told you.”
I wrote another option for Lyle’s text:
“There, I said, this one doesn’t even rely on that story about the ex-wife. It stands on its own.”
Lyle liked it, but again he tried to water it down. He told me, “Yeah… maybe instead… what if we just text:
I said, “Oh no… That’s not edgy. That’s just a “mistakeless and flavorless” text.
Remember, like Rob Judge says put your text up to the Grandma Test. That means, if a woman could get the same text from her grandma, don’t send it. Her grandma could absolutely text her, “(doing old lady Southern accent) “Well, sweetie, hope you fulfilled your bridesmaid duties.” There’s nothing fun about that text. You’re just sending that text because you’re afraid of making a mistake.
I asked him for more context that could give me ideas.
He said that he had been helping Allison brainstorm to prepare her bridesmaid toast. And when she had been brainstorming ideas, it was hard because most of her ideas were too risque and she kept cracking herself up.
So I wrote him another option for a text:
I hope you fulfilled your bridesmaid duties & gave a totally inappropriate toast. If not, I’ll be very disappointed.
Or an alternate version:
I expalined, “You’ve got to take the point of view that eggs her on to be more wild, that’s what’s fun to read.
Notice how using the language, “You better have…” as in “You better have given a totally inapprotiate toast,” is coming from a high-status position. You’re so interested in everyone having a good time, that you’re sort of commanding it to happen, you’re expecting that she’d want to live up your standards of fun. That’s masculine.
It’s masculine to write to her as if, in the world of this text, Lyle is in charge of what is an acceptable wedding toast. Now, is that true? Well it’s certainly not based in logic. But when you write as if it was true, it MAKES it true, because status is all about attitude. And when you assert yourself as high status AND you can make it funny, you’ve got an attractive text.
I came up with one more idea for him.
I explained: when a woman sends you a picture, you can also try to pick out some detail from the picture, maybe a detail she didn’t intend to be the focus, and make that the focal point of your text. It will surprise her.
So in the picture, Allison and the other bridesmaids were posing, looking kinda silly standing on two luggage carts. So I wrote Lyle this text:
It’s a good text. But he got nervous again and said, “I don’t know if we should make the comment about running over kids. What if we just say, “Looks like you had fun on the luggage carts.”
I told him, “No. That’s right back to a passive text again because you’re just observing her, you’re not ADDING any value that comes from your perception or your opinions. It’s when you add your spin onto things that it becomes masculine.
He said, “What if we just text, “I hope no one got hurt.”
I said, no, and even phrasing it as “I hope,” make you passive again. Phrasing it as “Promise me you didn’t run over any kids” is masculine because you’re not just passively sitting back and hoping, you’re actively telling her to promise you that she didn’t run over kids. You know how any book you read, the author has a certain narrative voice? Like, Stephen King is all grim and full of profanity or Charles Dickens is all long winded and old-timey, or the Hunger Games is written in present tense and really cynical? Well, you need to have an author’s voice in your texts and it needs to be IN MOTION, IN ACTION… masculine. Not passive and watching. So tell her “Promise me,” don’t just tell her, “I hope.”
Okay, so after that, we ended up with these great texts as options:
I asked him, what do all these good texts have in common?
He was able to tell me: They all pass the grandma test. They are all edgy and masculine. They’re ADDING SUBSTANCE to the conversation, adding either a new observation, a new opinion, a new expectation, or a new playful demand, all coming from you to entertain both you and her.
I said yes, and one more thing. Notice how none of them asks a question. Now, it’s okay to sometimes ask a question in a text, but that shouldn’t be your bread and butter. And in a case like this where a woman hasn’t been replying much, and you know she’s at a fun event and likely to be distracted, it’s a good idea to send her a STATEMENT, not a question, because if you send a statement and she doesn’t reply… technically she didn’t blow you off… technically, you just expressed an idea that didn’t require a response from her. You expressed yourself just for the hell of it and didn’t need a reply. Something to keep in mind.
So which one do you think he sent?
I told him to send the “riding on the luggage carts” text because it’s the text with the shortest life of relevancy, it had to be sent right then to respond to the picture. All the other texts could actually be kept and sent later on when she was still on the wedding trip.
So he sent it right as we ended our coaching call.
The next day, Lyle was doing another call with me, and he said that after he sent that luggage cart text, “She replied instantly. She’s never done that before.”
And he was glad he had the other texts, because he worked them into a texting conversation with her that lasted on and off through the rest of her trip.
We were moving things in the right direction.
A few days later, Allison came back to town, and Lyle wanted to ask her out.
He was thinking of texting, “Hey, would you like to hang out sometime this weekend?”
I said, “Once again, this text is lacking masculinity. It’s not asserting any idea for what to do, so it’s leaving that up to her.”
He said, “Well, I don’t want to be presumptuous and assume I know what she’d want to do. If she says wants to hang out, then I’ll ask her what she wants to do.”
I said, “No, man. You have to put forth an idea for the date, you’ve got to have a fun idea in mind and know exactly what YOU want to do. Again, that’s inserting masculinity into your texts.”
But first things first, don’t go straight into a date invitation without getting her having some fun texting with you first.
So I asked him, “What inside jokes do you have with her recently? I’ll write some fun texts based on an inside joke to get her warmed up, then you’ll ask her out.”
He said that the last time they’d hung out before she left town, she had said that she thought Megan Fox’s boyfriend Machine Gun Kelly was 6 foot 4. Lyle hadn’t believed her, so Allison had made a playful bet with him, she bet him that if she was right, he would have to buy her a muffin.”
I stopped him right here and said, “Allison is a very cool girl. She’s doing the work here that YOU should be doing, she’s making the conversation playful, making a bet with some stakes. She’s being more masculine than you, and that’s not good. That’s why she hasn’t wanted to have sex with you for a month. You’ve got to take the lead and do this stuff. It’s seeing your masculinity that inspires her to feel attraction.
So I wrote him this text, which has 3 parts to it.
First text this:
“Just found this about our friend Machine Gun Kelly”
Then send her a link to a google search result that shows Machine Gun Kelly’s height, which is 6 foot 4.
And then text:
“You totally cheated. No one would have known that without googling.”
I knew that text would go over well. But Lyle got nervous again.
He said, “Do I have to accuse her of cheating?”
I said, “Yes, that’s what makes the text fun. Trust me.”
He said, “What if I just text, ‘That’s really impressive that you were right”?”
I said, “No. Accuse her of cheating.”
Finally he took a chance and sent it.
Then I’m like, halfway through my next sentence to him and he interrupts and goes, “She wrote back immediately again, I can’t believe it, she never used to do that.”
He showed me Allison’s text, she wrote back saying “I didn’t cheat!” with a bunch of laughing/crying emojis. Immediate investment in the conversation.
So I told him to text:
“Nope. The system was rigged. I don’t owe anybody any muffins.”
She wrote back again immediately, laughing and insisting on having won the bet.
Showing a lot of engagement.
So I said, “Okay, Lyle. She’s having fun with you, so it’s time to ask her out. Let’s transition from this fun argument into the date invitation.
Now one reason Lyle was not getting sex anymore was that every time he hung out with Allison, she never wanted to leave the house. So every date was just him just going over to her apartment, sitting on her couch, and watching Netflix.
He was always showing up with no plan or activity, he was always on her turf, where she was inherently in the dominant role, she controlled what they watched, she controlled what they ate and drank, she controlled when it was time to go to sleep, etc.
So I said: this next date is make-or-break for you. Let’s make it easy for you to take the masculine role. Let’s invite her to a date on your home turf. And what are you most at home with? Music.
Lyle owns a recording studio in Seattle. He often scouts talent. So I had him write:
“Saturday I’m gonna head to Sunset Tavern to hear a new band play. Come help me decide if these kids have any talent worth scouting. Maybe they’ll have muffins and it will be your lucky night.”
Obviously that was a joke because no one’s idea of a lucky night is to end up with a muffin. But the key here was, this was a masculine text. It told her the activity, the venue, the night of the week, and it made it sound fun. And importantly, it coaxed her out of her apartment and out into the music scene where Lyle would naturally be able to take the lead.
But he was scared to send it. He said, “Well, isn’t that a little presumptuous for me to assume she’s free on Saturday? And to presume that she would even want to go, I mean, she might not want to go to a concert. What if I say… “What would you like to do this weekend? Which night would better for you to hang out?”
I said, “No, man. That’s going right back to lacking masculinity again. If you leave it up to her, she’s just going to want to hang out at her place and sit on the couch again and that never leads to sex because it’s not exciting. The reason she never ends up wanting to go out is because you never propose the plan in an attractive way. You should always come from the point of view of being presumptuous that she’d want to go. Because what’s the alternative? If you’re presumptuous that she WOULDN’T want to go, that vibe is going to rub off on her and she’s gonna sense your low self-esteem. Like, why would you assume that a girl WOULDN’T want to go out with you? Believe that OF COURSE you’re the best option for her Saturday night, of course she’ll have a good time.
And commit to inviting her for a certain night of the week. If she’s not free, she can always tell you and you can rework the plan to change the night of the week. But asking for a certain night of the week gives some momentum to your invitation. Once there’s momentum, it’s easier to work out the details like changing to a night that works better for her, picking a different concert.
What gets a woman saying “yes” to a date is when she receives a date idea from you all wrapped up in a bow, with the activity, the night of the week, the location, all planned out and ready for her to just say “yes” to, because that means you did all the masculine work and now she gets to sit back and just enjoy, without having to do that work for you. What you think of as being polite and overly presumptuous is actually you just making a woman do more work by forcing her to pick the night and the activity. She’s probably got a job and million other things she has to do, don’t make your date invitation feel like work for her, too.
Lyle sent the text. To his surprise once again, she replied right away and accepted the invite to go to the concert.
The next time he got on a coaching call with me, he started by telling me that he and Allison had sex that very night after the concert… after a MONTH of not having sex.
So the story here is, he’d been losing the girl of his dreams because he was lacking masculinity in his texts. But by injecting some masculinity, some edge, and some creativity into his texts, he was able to save the relationship.
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