TL;DR version: If you want to date, the best time to do it is 18-28. To do it well, you need to prepare while you're in high school.

Let me explain... while there are concrete benefits to monk mode, I side with Sandman's assertion that young men should date in their 20s to both be able to appreciate single life later, and experience the few good parts of relationships so they don't regret not doing so later.

Here's what I wish I would have known: AWALT. At the age when women are their most attractive (18-25), they are either looking for a resource or a sex toy. You want to be the sex toy. Why? Because there's nothing worse than having sex with a woman who isn't sexually attracted to you, and is doing it just to keep you invested in the 'relationship' because to her you are a resource.

Can you be sexually attractive to the young twentysomethings into your thirties? Absolutely, but hair loss can strike in your late twenties/early thirties. It puts you out of the market for a lot of women and it's something you can't fix and can't always plan for.

So you've got ten good years to go after women. How do you make the most of it?

Again, AWALT. In today's Western world, love is dead (if it ever existed). Either a woman wants you because she wants to bang you, or she wants you because she wants your resources or your status. To become the guy she wants to bang, you need to put in the work, and the best time to do that is in high school.

Why? Because you're not going to miss out by ignoring women and focusing on yourself in high school (gym, job, studies). First and foremost, adolescents are fucking crazy and any kind of relationship is just going to be a minefield. Second, unless you are exceptionally lucky, your hormones are going to screw up any chances of enjoyable relationships anyway, between acne, general teen angst, the the propensity to make stupid decisions (getting a girl pregnant). So why not build yourself up instead so that when you go to college or your first job, and your hormones are at least somewhat in check, you're ready to hit the ground running?

Here's what I recommend for you guys in high school:

  • Keep a small social circle of like-minded individuals. You never want to be the loner. Life is all about who you know, and if you let your social skills deteriorate, it will bite you in the ass later. Find three to four good friends, and by that I mean guys that would help you move, not the popularity bullshit games normal to your age group. And yes, guys. You do not want to be the guy whose 'friends' are women.

  • Leverage that testosterone. You'll never have as much coursing through you with as much time to make use of it. Hitting the gym now and getting as big as your genetics will let you will serve you well in life. Building yourself now will be much easier than trying to do so later.

  • Get a job/build skills. I did manual labor and apprenticed to a tradesman. I never ended up going into the trade, but it was a great experience that taught me not to be such a dumbass and put money in my pocket. Since you're not trying to attract women by being a resource, you don't need much, but you do need enough to get yourself a decent wardrobe, decent car and be able to afford going out every now and again.

  • Fucking study. I know it sucks. Most of what they teach in high school you will never use again, but that's not the point. You are learning how to learn, how to solve problems, and how to communicate. Those are the skills that will power the rest of your life. If you have control over your classes, don't waste time on bullshit. Knock out the core (math, life and physical science, English or your native language, history, economics, civics, and a foreign language). Ideally, pick a foreign language for a country with hot women. If you have the interest, talent, and most importantly extra time, then take a look at the arts or humanities. If you enjoy doing so, or want to go to college, I would suggest playing a sport. College admissions offices like seeing well-rounded people. If not though, spend that time working, studying, and building skills. Popularity alone is not a reason to play a sport - you're not going to remember who you went to high school with in twenty years, but you're sure as hell going to be dealing with the effects of a serious injury then.

Ultimately, when you hit the adult world, be it college or a job, you should be as physically fit, stable, and attractive as you're ever going to be. Put yourself out there and see what interest you get. Don't chase women (they decide within 30 seconds if they're ever going to sleep with you, and if not, will just use men who chase them for attention and resources). Rather, let them come to you. Don't get a woman pregnant (and I truly hope RISUG or something similar comes online for your generation), and most importantly, do not fall in love.

This last part is hardest, and it is the one true danger of dating in your twenties. For that you only need to read the life stories of the men on this forum to see where love ultimately leads you. Stay strong, enjoy what you can from the fairer sex, then go your own way once you've had your experiences.