First Experience

First times come with many unexpected facets and is often accompanied by awkward moments. Think about how many graceless stories you've heard about first kisses. I refuse to believe anyone has had a straightforward dull first kiss experience, whether it be the anticipation leading up to it or the anticlimactic/revolting kiss (What to do with the tongue?!). But it's not the overall act that's makes it difficult. It's the intricate little things that makes it daunting, like arm positioning with hugs and its timing.
You can observe someone do something over and over but until you do it, you really don't understand all the aspects that come with it. For me, golf is probably the best example of this. The professionals make it look so simple but once I hit the links, I can barely make consistent contact (with some complete whiffs). Before last year, I thought I could pick up the game easily; I couldn't have been more wrong. There may be nothing more entertaining than someone playing tennis for the first time. It reminds me of how awkward playing a racket sport can be if you never played one before; everyone has gone through that phase at one point.
Some things that were much more complex than expected: Silk-Screening, Wood Carving
Discussions can also help prepare for something but once again but carrying it out encompasses so much more. As much as I have talked to people about relationships (and even giving much advice about them somehow), I am prepared to encounter particulars of relationships that I never would have thought about. I'm sure some of them will be annoying, others will be exciting, but I'm eager to take part in it.
Even the best storytellers cannot replicate the feeling of doing. While film has made great advancements, there will never be a replacement for actually being somewhere. I've watched videos of national parks and listened to stories about them, but nothing compares to being there. You don't comprehend the size, the beauty, the smell, the feel, and so much more that cannot be communicated in words/pictures/videos.
So the lesson here? Experience. You can read/watch as many books/movies/videos/pictures but it won't come close to doing it in real life. Experiencing will make you feel alive, create your story, and help understand the many idiosyncrasies in life. In turn, you'll further understand and connect with people.