I've worn glasses my whole life, except for a short time in early high school when I pestered my parents for contacts. Mainly because a friend got them and I was so envious of how she looked without her glasses. At first I loved the freedom of not having to rely on my glasses (which I absolutely do need to see!) But contacts were hard to put in (at least for my eyes) and really annoying after a while. So by year 9 I went back to glasses and was very comfortable with how I looked. Having the right frame and high index lenses definitely helps if you have a strong prescription. I dated a lot in high school and later in uni, always in glasses. Usually guys are very curious about my glasses, like whether I could see without them (um, no) and why I don't wear contacts (don't have a good reason to). But I do get many compliments and never any negative comments.