I started wearing glasses in the 4th grade. I don't recall any big "I can see clearly now!" moment. It just was the way it was. Glasses seemed to suit my personality (nerd!) and I was fine with wearing them.
Then towards the end of my junior year of high school, when I still wanted to be an actor I decided I should get contacts so I didn't have to worry about wearing my glasses and/or squinting a lot onstage- only to be asked to wear my glasses in the first show I did after getting contacts. Ah well.
When I got those contacts I was honestly excited by the idea that I'd be wearing my contacts all the time, then one day I'd wear my glasses for one reason or another and someone would say "Hey! I didn't know you wore glasses!" It would be proof that I'd moved on from being the dork with glasses or more likely that I just wanted to be surprising to someone in someway.
Yesterday a co-worker asked about my glasses. I think I surprised her with my excitement about her question. She didn't know that I'd been waiting eight years. Of course even after all this time, I still have a preference for purple frames.