Look at it this way:
Experience is like wine. It gets better with time. I'll talk about the lover aspect later
Heartbreaks and the stress aside, the more one is knowledgeable about this things, its usually the better, because i have come to realise that at the end of the day, THERE ARE MANY THINGS THAT NO ONE WILL TELL YOU ABOUT RELATIONSHIPS, but
you are expected to know. That's why you see threads like "she did this and that" and people reply "r u stupid? can't you see the writing on the wall?" A guy who gets dumped 3 times in a row might see a pattern and derive a conclusion on how to "see the writing on the wall" and take action.
The world is a terrible place. Playas and Hustlers, stalkers, unstable obessesed psychos and serial daters are mixed with the good people. How are you going to sort them all? This is where experience comes in. And you don't get it in textbooks. You get it on "the field"

As for the lover aspect, its ironic. Guys search for virgins, but women prefer a guy with "experience". How does one get this experience?

General consensus demands that the guy must be capable in THAT department. Afterall, is it just your mind when you feel you should be the one to take charge in bed, at least most of the time, but you haven't done "it"? So you get nervous, and then she senses this, and after all is said and done, you mention the worst words ever: "DID YOU COME?". KAI! Experience!
As a mentor of mine said, its the little things that matter. And you only learn this by what? Experience!
A girl slapped her boyfriend when he asked for a bl*wj*b outright. Why? cause he asked outright! Nlanders told him to guide her codedly. Would that happen again? No, because of experience!
We all are the sum of our experiences.