Should You Text First? A Modern Guide for Men

Why are men struggling to date in 2025? As I sip my coffee and stare out of the window overlooking the bustling streets of NYC—the taxi cabs honking their horns, the people moving swiftly as they go about their day—I see it: a man sprinting towards a woman who happens to be heading eastbound with a cup of coffee in hand. He calls to her, “Hey!” Unsure of who he is speaking to, she remains unfazed, keeping pace. Then, he calls again, “Hey there, red coat,” and suddenly, she turns.

This brunette bombshell is intrigued, and once they lock eyes, he approaches her, asking for her number. I watch intently from my upstairs window as though I were a bird perched on a branch in a nearby tree. He gives her a compliment and follows it up with, “Do you mind if I get your number? I’d love to take you out sometime.” She smiles, and you guessed it—she gives him her number. This is the standard and has been for many centuries: you see an attractive woman, approach her, take her number, ask her on a date.

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So, are men struggling to date in 2025, or have they simply complicated the act so much that now they themselves can’t find the solution to a problem they created? The question, “Should I text a woman first?” is downright silly. When you make the conscious decision to do something, you are actively looking to make a change in your life. Actively seeking a partner, whether on a dating app or in person, means you are seeking a change in your day-to-day life—whether that is companionship, a relationship, or even to cheat and create strife in your marriage.

When you start going to the gym, you do it to change your physical appearance. When you go to the supermarket, you do it to have a meal the next day. When you go to work, you do it so you can earn a paycheck. Why should approaching a woman be any different? Oh, because she’s another human being who you may possibly look down upon, and so you’re grappling with misogyny? Why else should actively pursuing a woman be looked at as being so trivial when compared to other things in your life? Men do know that they can remain single and never approach a woman, ever, right?

The men’s proximity rule is an observed dating and relationship pattern where men who postpone marriage and commitment until late in life ultimately settle down with the most conveniently available partner at the time they are ready—rather than the woman they once deeply loved. As Miranda Hobbes put it, “Men are like cabs. When they’re available, their light goes on. They wake up one day and decide they’re ready to settle down, have babies or whatever, and they turn their light on.”

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Also known as the Cab Light Theory, this concept makes men more confident in approaching women because they have a goal in mind. Perhaps you spent most of your early twenties prioritizing your career and personal growth. This means that you were not interested in properly approaching, let alone courting, a woman—and that’s perfectly okay as long as you were honest about it. The problem with dating today is not that women want to use men or that men have a growing fear of commitment due to all of these “options” on social media platforms—it’s a lack of information and honesty.

If men were honest about their intentions from the beginning, there would be less cheating because fewer women would enter relationships. This behavior highlights how timing and emotional readiness often play a more significant role in men’s long-term relationship decisions than deep connections from their past. Men with good intentions and integrity, who have their taxi cab light on, will never have to wonder, “Should I text first?” because they are not willing to risk losing what they want. Men are selfish; they will almost always prioritize their needs and wants above everyone else. This also applies to the women they pursue.

It’s no surprise that some men will stay in a woman’s life for years, playing the friend position until he sees an opening where he can make himself known as more than that… all in the name of "conquering the quest." If your aim is to "get the girl and love the girl," then why would you ever need to wonder about her level of interest once she’s shared her direct mode of communication with you? This question leads to a larger problem in dating—fear of rejection. Men fear rejection so much that even when all of the signs say GO, there is a small voice in their head that says STOP—overthink, overanalyze—and all of those things point to insecurity.

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If you’re insecure, then you should not be looking to date anyone. You need to focus your time and attention on healing your trauma and working on your confidence. An insecure man will never make it far with a woman he’s interested in and then will go on to blame all women or social media as a whole for why he’s failing at securing a romantic partner. All women aren’t looking to be with a man for money, and all men aren’t looking to be with a woman for a situationship.

While we’re constantly hearing men say things like, “Not all men,” when general conversations are held, it’s okay to remove yourself from the stereotype by simply acting upon your desired outcome. Don’t be the guy with the low IQ who is chronically online and listening to losers who can’t land themselves a date; otherwise, you will, in fact, become a statistic. Expand your reach, go outside, speak to a lady, and court her with good intentions. The odds will almost always be in your favor.

Should men text first? Yes.

by Lisa K. Stephenson