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Benefit from My Mistakes: Read His Intentions in Record Time

When it comes to dating, one of the most powerful tools you have is discernment. Despite the noise, the memes, and the think pieces, a man’s intentions are rarely as complicated as they seem. If you’re paying attention, and especially if you’re looking for something serious, his actions will tell you everything you need to know.

Let’s break it down.


1. He Gets Offended by Your Standards

If setting expectations, like wanting consistency, clarity, or actual dates, makes him call you “demanding,” “high maintenance,” or “too much,” he’s already told on himself. Standards filter out people who aren’t willing to rise to the occasion. If he’s offended or you’re having to consistently ask to be treated appropriately, he was never intending, willing, or capable of delivering.


2. He Relegates You to Social Media Platforms

If a man keeps all of his interaction with you on Instagram, Snapchat, or Twitter DMs, that’s not courting, it’s containment. Men who are intentional don’t hide behind apps. They transition you into their real lives. When a man keeps you confined to social media, it’s usually for one of two reasons: he’s already committed elsewhere and can’t risk you showing up in his texts or call history, or he’s juggling multiple women and finds it easier to keep you all neatly separated in different apps. Courting is about access and intention. He should want to hear your voice, plan real dates, and make space for you in his day-to-day. If you’re not in his phone, you’re not in his plans, and if
you’re not in his plans, he’s not building toward anything real.


3. He Lowballs the First Date (And He’s Over 30)

If a grown man over 30 suggests “pull up and chill” or a quick coffee run for a first date, he’s showing you where he places you on his priority list. I once dated a man who didn’t have much free time and had most of his money tied up in investments, but he still planned a museum tour and a sunset picnic for our first date. At this age, he’s had years to figure out that first impressions matter. Coffee isn’t a crime, but as a first date, it’s the dating equivalent of handing you a sample cup at Costco: low effort, low cost, and easy to dip out of in twenty minutes. By the time a man hits his thirties, he should know better than to approach dating like a teenager. Intentional men put in thought because they understand that effort is the difference between casual and serious.

And for women who say, “Well, I just want an easy way to feel him out too” — no. You’re not being efficient and clever. You’re signaling that your standards are low and it teaches him early on that the bare minimum is enough. You’re not just being cautious. You’re literally showing him you’ll accept less, and men rarely volunteer to raise the bar once you’ve set it that low.


4. He’s Never Lived On His Own

Still living with his parents or bouncing between roommates with no real sense of independence? That’s not just about his address, it’s a reflection of his readiness for partnership. A man in his mid-twenties who hasn’t yet established independence, isn’t looking for an equal. He’s looking for a caretaker and/or a roommate. Ignore this red flag and you’ll quickly find yourself doing his laundry, managing his emotions, splitting the bills he can’t cover, and carrying responsibilities he should’ve mastered on his own. He’s recruiting you to be Mom 2.0. If you’re a single mother, be especially wary of these types. They prey on women who are responsible and are active caregivers.


5. He Avoids Asking Direct Questions or Clarifying Intentions

If he avoids defining the relationship, refuses to make plans beyond the moment, and sidesteps any conversation about exclusivity or what you both want, it’s not an oversight, it’s intentional. Vagueness benefits him because it keeps his options wide open while keeping you in limbo. A man who genuinely sees a future with you won’t dodge clarity; he’ll want to make his intentions known. If he’s unclear, it’s because clarity would expose the truth: he doesn’t see you as long-term.


6. It’s Been Over 3 Years, and Marriage Hasn’t Come Up

If you’ve been with a man for years and he hasn’t once brought up marriage on his own, he’s not unsure, he’s uninterested. Men know within six months if you’re the type of woman they’d marry. And don’t confuse him wanting you to have kids with him with wanting a lifelong commitment. Sometimes, fatherhood is just a way to secure permanent access to you, control your mood, and limit your connection to other men. If it’s been three years without even an unprompted hint of marriage, accept that you’re not his dreamgirl. And you need to be his dreamgirl to sustain a happy, healthy marriage. Nothing less will do.


7. “I’m Still Healing and Not Looking for a Relationship”

The unspoken part? “…with you.”
If someone genuinely isn’t ready to date, they shouldn’t be dating. Period. But, if he’s consistently in your DMs, flirting, making plans, and treating you like an emotional crutch while claiming he’s “not ready,” what he really means is he’s not ready for anything serious with you. Emotional availability isn’t about saying the right words, it’s about aligning your actions with your intentions. If that alignment is missing, so is the respect.


8. He Leads With a Sob Story

Be cautious of the man who opens with tales of heartbreak and betrayal. True vulnerability builds over time, but when it’s used upfront, it’s often a tactic to earn your sympathy before he’s earned your trust. As I explain in another article on this topic, this approach isn’t about connection, it’s about control. If his first move is a sob story, he’s not inviting you in, he’s lowering your guard.


9. He Says His Ex Took Advantage of Him

This is the cousin to the sob story. If he frames every past relationship around how his ex “used him,” “took advantage of him,” or “never appreciated him,” especially early on, pay attention. He’s not just sharing, he’s setting the stage. By painting himself as the perpetual victim, he primes you to prove you’re different, to overextend yourself, and to accept less because he’s “been through so much.” What sounds like vulnerability is really a script to lower your standards. Instead of asking what he’s learned or how he’s grown, you’ll find yourself tiptoeing not to become the “next villain” in his narrative.

10. He Can’t Stop Talking About His Ex

If a man constantly brings up his ex, he’s not over her and he’s using you as an emotional crutch while he sorts out feelings he hasn’t resolved. Often, he’s still trying to figure out how to get her back after walking away, and if she left, it’s even worse. He’ll stay stuck in “what if?” mode for years, and you’ll end up as a temporary band-aid or placeholder until he either gets another chance with her or finally heals. Men can move on physically, but real love for many is fueled by stress and attachment, not emotional connection. If his past is still the focus, you’re not his future. Move on—and do it fast.


When He Does Have Good Intentions

Not every man is a walking red flag. Here’s what intentional, emotionally mature men do:

Effort doesn’t necessarily mean extravagance. It means presence, clarity, and thoughtfulness. A man with good intentions wants to earn your time, not waste it.

I’ll never forget one moment that showed me what real intention looks like:

I was out with someone I’d been dating for a few months (not my most recent ex, but someone I had a genuine connection with a few years prior). At some point during the night, someone referred to him as my boyfriend. I quickly corrected them, saying, “No, he’s not my boyfriend.” I didn’t think much of it, but I noticed the shift in his demeanor. He got quiet. I asked, “What’s wrong?” and he looked at me and said, “Would you be my girlfriend? I’m tired of not being able to say that, and it’s what I want—if you do.”

I will remember that for the rest of my life. Because real intentions don’t play games. When a man knows what he wants, he acts and does so with purpose, before it’s no longer an option available to him. If he doesn’t? He doesn’t know what he wants.

Don’t waste your precious time while he uses you as a trial run while he tries to figure it out.

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