My daughter was determined to be borderline needing glasses about half way through 5th grade (when she was 10 1/2). She needed some correction, but it was mild and even the lowest prescription would be a tiny bit more than what she needed, so it wasn't necessary. By midway through 6th grade, she mentioned that she was having a difficult time reading the smart board at school. It was't b/c of a blocked view (other kids' heads in the way or other obstruction), but b/c her vision had changed enough that correction needed to happen.
We went and had her vision tested again, ordered glasses. When they came in, it took a while before she wore them for any length of time. Mostly she'd take them with her in her bag and only pull them out for the classes she was having difficulty reading the smart board in. But as she became accustomed to wearing them (when you first begin wearing them, they can give you a headache b/c of the abrupt adjustment in your vision. It can take a little getting used to), she began wearing them more often.
She is an avid reader, so she was wearing them at home to read, and most of the time at school. She did not wear them in her martial arts classes, or sitting around at home playing video games, watching TV, etc. But she plays piano, and she began wearing them when she played (so she could see the written music more clearly).
Now, 2 1/2 - 3 years later, she wears them almost all of the time. In fact, I noticed her in the kitchen Saturday afternoon (after she'd taken a nap) and it took me a moment to realize why she looked so different. She didn't have her glasses on.
I've never had to encourage her to wear them, or not to lose them, or take care of them in any way. She hasn't expressed any interest in contact lenses, even though I've asked her to let me know if she wants to try them. (Teens and glasses, appearances, inconvenience of wearing them in the heat/sweaty conditions/rain, etc)
I would say that if your son is not having problems without wearing them (he isn't making mistakes in his school work due to vision issues) then let him decide when he is ready. I would NOT give him contact lenses until he wears the glasses routinely, personally.
I find it odd that he has headaches when he is not wearing his glasses, though. Is he far sighted or near sighted? I am very near sighted, and the only time I can recall EVER having vision related headaches, was a short period of time (about 4 years ago, so when I was about 42-43) when my vision IMPROVED and the glasses I had been wearing became too strong for the correction I needed. I went in expecting to need a stronger prescription and it was the opposite. I needed a weaker prescription. That's the ONLY time I've had headaches related to my vision.
That may not be how it works with other people, but since that has been my personal experience, it makes me at least ask the question regarding his vision correction.
I will warn you as well, when someone first begins wearing contacts (if you should decide to go that route) there is an adjustment period with those as well. He will not be able to put them in and just wear them all day right away. The first few days it will be for 4 hours at a time or so. Then after a day or two, upped to 6 - 8 hours. And after a time of adjustment, he'll be able to wear them all day, most likely. But, all day is a long time (not just 8 hours, but when he gets up and gets ready for school, 7 a.m?, until he gets ready for bed at night... 9 pm maybe? You're taking 14 hours or something... he will not be able to do that right out of the gate. So he wouldn't really be able to wear them to school right away anyway.)
How long has it been since he got the glasses? It might be time for another appt anyway to see if his vision has changed any. Even though he chose the glasses and you think they're cool and lots of your family wears them, he just may find them annoying. Because, well, if you aren't used to them (and sometimes even if you are) they are just a pain to deal with. They fog up in the humidity, they fog up in the cold, they get wet with the rain and you can't see through them, they can make your nose sore, or year ears, or if you fall asleep with them on they make the sides of your head behind your ears sore. And your peripheral vision range changes... if you aren't used to wearing glasses, you can visually be bothered by the frame itself. Or the edge where the correction stops and uncorrected vision begins (peripherally to the lenses). And they can make you sweat around your eyes, and slide on your nose.
If you have oily skin the lenses stay oily and need constant cleaning, too.
He will eventually come around when it affects his quality of life for the worse to not have corrected vision. I'd let that do its work. But if he hasn't been in for a while, another vision exam would still be a good idea.
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ETA if it turns out that he doesn't like his current glasses (style/frame, etc) and his prescription is up to date, you might consider letting him try another pair (or two or three?). There is a company called Zenni optical that is much better priced than buying glasses from your optometrist. My glasses normally run in the $350 range when I buy them at my eye doctor. But I can get a pair at Zenni online for $17 (including shipping!). It could be a less expensive way for him to try a few different frames.
I HATE trying on frames at the eye doctor's office, b/c, well, they don't have my lenses in them and so I can't SEE what they look like on me very well! I used to wear contact lenses to my vision appts just so I'd be able to see when trying on new frames. LOL
But, I dropped my glasses in a doctor's office (putting on the gown, ugh) and I decided it wasn't worth spending another $300 for the next few months before I was due for another eye appt. So I went online to Zenni. You upload a pic of yourself, and click the frames you'd like to try on, and you can see them on "yourself" online before you order. :) I get the non-glare coating, etc, and my last pair was $16. Delivered to my door. They arrive in a hard plastic storage case, with a cleaning cloth included. Exact same correction quality in the lenses as far as I can tell. They even sell sunglasses.
Just a thought.
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Sorry to add again, but good call Diane B. I hadn't even put together the other posts and things going on in the household. His reluctance (refusal?) to wear the glasses might very well have some connection to not only his need for some control of what's going on in his life, but also a means to maintain the status quo, which he is losing. You know the young mind and it's faulty logic: Maybe if I can keep everything the same, nothing else will change, either..