I'm a glasses guy and my wife wears both contacts & glasses. She is planning to have PRK (laser surgery in Feb) however. My dad is actually an eye doctor so I have a little insight on this subject. Your eye doctor should be able to get you some trial lenses fairly cheaply that you could try out and see what you think. I believe it really just comes down to getting used to wearing the contacts (putting them in and taking them out), but you'll always need glasses as a back up or to give your eyes a break unless you can function normally without correction.
My sister tried contacts, but was never successful because they always suctioned to her eye and would even leave a red ring on her eye. At first she wanted the with the color contact first came out so my dad let her "play" with them without success. I have never had any interest personally. Generally, people with really poor vision can get a better correction with a contact lens, it has something to do with astigmatism or something like that.
I say spend a few bucks and try a couple of pairs out, the disposable contacts are good for about a month and the doc might be able to get you a couple free pairs.
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