That's true, but for the first few months, Reddit was not like Usenet, mailing lists, or message boards at all. There were no text-only posts (and certainly no image or video posts), nor were there comments. It was purely designed to share links to other websites.
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Assuming his family is extremely wealthy, the stakes might not be as high for him as that number makes it sound.
A gift of jewelry suggests an infatuation to me regardless of price though, so it might be good to talk with her about how she would react if he didn't just think of her as a friend.