Actually there are plenty of people who would do something like that for their friends. I don't know much about the dating scene but I have a number of friends who do dedicate time and money to arrange dates for their friends. I'd say the benefit you get is the satisfaction you gain from helping out a friend.
It's usually because the ".com" version of the domain is taken and the sites cater to a more tech savvy audience. I'm not sure I've seen examples of medium or large companies/services using .io domains. (Exception would be survey.io, but it's a few years old)
As psycr says, it's also a reference to I/O and could also represent 1 and 0.
It looks like YC is actually shifting to investing in products that have a real way of generating revenue this time. I'm not sure if this is a trend in the whole VC community though.