I'm 29, and I feel like alot of you guys.
Highschool.....when I look back on it, it was a joke. The place I went to was a dump, totally over crowded, terrible "education", you're confined all day. I think even if you're really confident with women in highschool, go to prom, getting experience....you're still a teenager.
You worry about whether you're wearing your backpack the right way. When I was in highschool, Cross Colors and beepers were the coolest things. Really, that's a very very tough age.
I could have done alot more in terms of experience, but I'm also really glad that I've gotten past that stage. I'm much more comfortable with my looks, wardrobe, style, much more comfortable around people.
-My self education has improved dramatically. I've probably read 150-175 books in the last 5-7 years on all kinds of subjects. Women, business, finance, biographies, current events, self help. That's been a big plus. You can never stop learning.
-More varied interests, hobbies, lifestyle. I belonged to Toastmasters a few years ago, that was a good experience. Met some really nice people, flirted with some hot mid 30's professional women at some of the parties thrown by one of the hosts.
In your teens and early 20's, you live a very sheltered life.
Your "growth" as a person is usually heavily controlled/defined by school, and whether you've grown in a certain subject, or whether test scores or GPA has grown.
Between school, homework, tv, misc...you have very little time to actually work on yourself or even focus on it. That's something I've really noticed as I get older.
Life was really confining and strict back then. You're in school 7 hours a day, 5 days a week, 9 months out of the year, for almost 17 years! From kindergarden, age 5, to age 21, 22, 23.
The beauty of getting older is that you have so much more time to work on yourself. Look at this site....you can learn about things you couldn't have even dreamed of earlier.
I realized a few years ago at 26, 27, that I was where I should have been at 18, 19, 20. It's like ok..."from this day forward, this is what I should have been doing at 20."
To catch up, consider getting rid of tv, talk radio, and really trivial things people do. Besides a little tv at night, I watch maybe 2-3 hours during a typical week. I have *alot* more time to work on myself, my goals, surf the web, plan my life.
I've thought alot about my overall life strategy, what I want to do, accomplish. The really big things for me were...
-Highschool Degree
-College Degree
-Own a house
-Debt free
-Experiences with women
-Learning/growth
-Travel
-Trying to have a good time along the way.
Not taking things too seriously or too strict.
If you're 26, but you feel like you're 18 with women and dating for the first time....it's 8 years, but I dont think you would have had 8 years of continuous relationships and a perfectly smooth ride up. That might be low confidence talking, assuming the best would have happened, and now you're in the worst position.
In the big picture, I think college degree, owning a house, no debt, no addictions, growing/learning....those are the most important things. With women.....you really can't control that. What if she turns out to be a pyscho, what if she moves away, what if you get attached and wonder if you'll ever date other girls..
Not to get too philosophical or mystical, but people live so close to their dreams. You go through life within inches of what you want. All you have to do is reach over and get it.
-Getting a girl in bed starts by saying something. I live in a big city, there's 2 million women here, how hard can it be?
-People agonize so much over their clothes, their style...what am I going to wear?? Is it cool enough? Will it make the right impression?
And you live 10 minutes from any type of clothing store you want. You can try anything you want.
-You worry about where to live or where to go. Is this the right neighborhood? Is this the right area?
And you live in this huge country with so much variety...the beach, the desert, mountains, ocean.
-In terms of entertainment, nightlife, restaurants, you've got places all over the world to go to.
Getting back to the OP and original question, your first experiences are important, in your teens and 20's. They definitely form a part of your overall life. I would try to focus on experiences and events more than trying to find the perfect person.
Get rid of as many distractions as possible, focus on what you really want. Live in the present.