I had braces in high school and never had a problem with it, though I'd always wait a day or two after a tightening. You might want to grab a slice to experiment with beforehand, though, just to make sure you can.
I think that relies on the crust been the problem really, depends on how tough the crust is. Soft crust should be fine. Tough or thin crust won't be. So really up to your judgement of were to get a pizza that's soft and don't damage them on that.
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I had braces for two years in my teens and don't remember there being an issue with pizza. I was always told to avoid popcorn and celery, but those are the only two foods I can think of. I know I ate pizza during that time, but never had an issue.
All your dentist. It doesn't seem wise. Just use a fork. If that bothers him then he's way too fragile to be worth dating.
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