I just graduated high school and a bunch of my teachers told me to stay in contact with them. Do they actually mean it? And if they do, do they mean to just send them updates about my life every couple of months or so?

Definitely!  They wouldn’t say it if they didn’t mean it.  Maybe 1-3 times a year?  Otherwise it would be pushing it into staying in touch as friends and not everyone has time for that (both you and the teachers).

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