Remember that making mistakes is human.

As with any endeavour, you will learn as you go.

Having said that:

• a healthy relationship does not mean you will agree on everything and anything. The important part is being able to have mature dialogue.
• condoms. buy several and try on your own how to open one. how to use one, and how to remove it. Non-negotiable. Condom. 100% of the time.
• look how she interacts with those on a lesser position. It is easy to see people be kind with their betters, but it is far more revealing about their character when you see how they treat a friend down their luck.
• digs at your maturity or lack thereof. Understand that women are at their peak in attractiveness and then they decline. you, on the other hand, are going on a longer curve. Your prime is 35+, when you acquired your status and resources. So don't sweat it. Also, it does not matter what you do with your free time, be it Netflix or playing games. I am married, I support my family, and I have plenty of hobbies. By the metric of "playing games" I am a kid, since I DungeonMaster DnD games, hell, I spent several days crafting Tiles for our next campaign. Maturity is being able to postpone rewards. If you fulfil your obligations, you can do with your free time whatever strikes your fancy. Since you postponed your "reward" (free time) after you fulfilled your duties. That makes you by definition, mature.

-You are already winning. Women are attracted to "social Proof". So now that you caught the eye of one, that means you "have something" interesting going for you. Cue the next one thinks you are a greater catch even if you are exactly the same. It can be illogical, but that's how it works for feminine stereotypical psychology.

-pay attention at what they DO. Do not take them at their word. It bears repeating. Look at what they DO. If they understand credit balance and are saving for something, that is an indicator of their ability of controlling impulses. Tattoos everywhere and piercings everywhere aren't bad per se. Since ink is a substance and a piercing is a ring. But the information they relay may be categorized into "Gives into sudden wants without concern of impact in her career" or "gives into peer pressure". Rollo tomassi got a list of red flags, by itself a single one isn't important. Is the issue of trends that makes you open your eyes.

-body language. If she is interested, you may see how she closes the gap. How her posture changes. Pay attention not at her words but at her body language.

-this is the big one. LIMIT the time. It is really weird and I would have not believed myself but the nature of the beast is this: we want titties, they want attention.

Again, Limit the time.

If you are always available, that lowers your value. If you are a scarce resource, she feels that she needs to compete to "earn" that attention, and then it increases her interest. Weird huh?

"This weekend I am helping Fred with his car" "I am going to be painting my niece's room" "Etc." That means you have STUFF to DO. Women are, men DO. So learning to DO stuff is a desirable trait. But that limits your availability, which, we would like to share cuz more time would mean more titty proximity time.....but that would in reality lower your tity chances.

So do not be afraid to be firm with saying "no." Paradoxically, even if they argue, that means you got STUFF to DO.

I remember when I was a virgin, I would allude that I've dated other girls before but never went into too much detail (because I was lying lmao).

When you do have sex, wear a condom. Not only will is it safe, but it will help tremendously with preventing premature ejaculation from being a virgin. I was terrified of blowing a load within 5 seconds because of all the horror stories I read online, only to wear a condom and last about 30-40 minutes of on and off sex. (There were times I was sucking her titties and not penetrating her.)

Yeah you'll probably fail all her shit tests, lose frame, develop oneitis, and get dumped. Better have several women lined up. Scarcity makes men do stupid stuff.

My advice: Never marry your first piece. My granddad warned me about this. I didn't listen. HUGE mistake. It doesn't matter who the girl is. She's not different. She's not special. Don't be stupid like I was.

On your first date have fun and don't stress it. Save self reflection/analysis for later. No need to overshare things you're insecure about, steer conversations to things you want to talk about. If you ask her questions about herself she will probably do most of the talking for you. If she's into you there's very little you can do to fuck it up.

You're doing great.

Virgin: it's fine, don't tell her.

See sex and dating as a journey. This girl isn't the destination, she's part of the journey.