Three Tips for Guys Dating in 2025 - With Context

Enjoy each other's company!

I've got a slightly different post for you today, and I want to get right into it. The video is available on my Youtube channel and my podcast on Spotify if you'd rather listen or watch.

My goal here with this piece is to give just a little background on me, and why/how I came up with these three tips.

I never dated in high school, my only relationship was a church one, with a girl I'd literally see only on Sundays and at events. It felt more like a middle school type of thing if I'm being honest. I almost landed my dream date for homecoming, but I found out with a week left to go from word of mouth in school that she was ACTUALLY going to go with the guy she had broken up with.

My first year in college was more of the same. I still had never made out with anyone, still wasn't drinking, and was still wearing whitey-tighties. I got invited to hang out with a bunch of girls as they were getting ready to go out because I was the "nice" guy and had NO idea. All the girls always thought I was a nice guy. It was because I had no intention of breaking my religious virginity contract. Yeah, I may have had the 18-year-old body of a Greek god, but I had never even made it to French-kissing yet.

Then it happened. I had been invited over to "hang out" with a girl who I knew had an interest in another guy. And as I walked into the dorm, I saw the guy leaving her hallway. While I was a little hurt inside, I understood. My whole life up until that point was just watching guys get chosen over me, even though I was "nice."

So, I started reading. It was 2003, and I was sick of being nice. I read article after article on being a gentlemanly a$$hole. And it was disturbing how it worked. I honestly hated being that guy, but the results it brought were undeniable.

I pretty much got what I wanted, mostly from who I wanted, but it was also thrown at me. Most times I said yes, just because I could. Even when I tried to say no, they doubled down. So, if anyone knows that most women don't really believe what they say, or that they tend to follow the crowd more, or that 99% of them are not ready for actual stability until they've been through it enough, I'm sorry that I may have been that lesson for some, as they were also for me.

This a$$hole stage lasted through college and probably up until around 2020. 2020 is when I lost my last long-term relationship with my partner, who chose her sous-chef while I was busy trying to make something of a previous podcast and Youtube channel. But how we had gotten into that relationship was exactly the same. I was her personal trainer, and she had a boyfriend. Live by the sword, die by the sword. Everything always comes back in a way. We broke up and she quickly moved on, as per usual for women, and I had to sit back and wonder what happened.

It's why I'm finally in another single phase, and have the perspective to actually see what works, and what works with honesty and truth.

Why am I telling all of this? I have been THERE. I have DONE THAT. All of it. Anything you can think of happening, I've actually done it, been in it, seen it, been around it. With that, let's get into what actually works in 2025, in the healthy way.

Dating Rules for 2025

Vet Yourself First.

What is it that you "want" from her? I feel like going into a relationship, on either side, wanting anything from someone, is what leads to disaster. Just because you want something doesn't mean that you don't want to give something back, I do recognize that, however, it's what you lead with that matters the most.

Do you just want to see what they look like without clothes on? Do you just want sex? Do you actually like her? If so, why? Remember, admiration, respect, and mutual interest are the three keys to starting a fantastic long-term relationship where both parties are on the same page. With those keys, both parties approach the relationship completely differently. Those keys make you more patient when developing a relationship with someone.

My experience tells me that developing a relationship any other way, especially with sex first, can lead to problems.

Lead as a man but pay attention to her cues.

We should be taking the lead in specific areas. The thing that we automatically shy away from when it comes to women is probably the area that we need to learn to lead in.

Personally, I took the lead in disciplined areas, things that required discipline. I never took the lead to do fun or exciting things that women enjoyed. I realize this was a habit I picked up from my father, and one I have let go of.

A woman will give us so much information through body language, subtle words, subtle looks, and things she will say over and over. I know men have been accused of low emotional intelligence and not being "vulnerable" but it definitely takes one to know one. Women also need to tell us exactly what's bothering them, and a lot of them do, and that's why paying attention is what matters for us men.

The next part of this paying attention is being able to see if she can pick up what you're putting down. This works from her side as well. What I'm inferring by this is figuring out how easy it is to understand each other.

Have you noticed this in your relationships? The misunderstood part of this is that it should be natural for you to speak and interact with someone. If you find yourself changing, and not in good ways, it's a good indicator the relationship will not be healthy for you. People should be able to be themselves when around people they love, but most of us find ourselves changing to make someone else happy, thinking that the making them happy is what will satisfy us. This is the first step in losing a relationship, because eventually we become unhappy.

Take turns naturally initiating conversations, don't force anything anymore.

No more forcing things to happen. I believe the first two parts of this discussion should be giving us that information, but it needed to be said.

Don't always wait for the other person to reach out, recognizing that other people may feel exactly like you do. If we are all waiting for other people to reach out, we will never develop the relationships that we desire to develop.

No need to try to push it, no need to try to play games with it. Ask people about themselves, and if they respond, continue. If not, well, take a step back and do the first two things and see where that lands you.

Enjoy the time spent

This needs no explanation. If you don't enjoy it, take a step back. Life is here to be enjoyed.