It depends on the legalities of the country, state or province that you live in. The laws vary.
At 16, what is the oldest I can legally date?
Actually, there is no legal age for who you could date, it's the legal age you can have sex with them. The legal age of consent varies with each state. In some states the legal age is 14, in Wisconsin it's 18. So you would have to look up what ever state you live in. BUT, if your just going to go out, and enjoy each others company with no sex, there is no age limit.
well if your 16 then somebody either your age or like 18 that's not bad . I hope I helped you.