Have you seen this op-ed in The New York Times? It's interesting and I agree with it. When people are faced with too many choices, they can't make decisions (that theory really came from The Paradox of Choice, which I have read, it's a really interesting book).
In terms of dating, I don't think technology has helped us. It's made finding people more difficult because there are too many choices (not all good choices). People rely on the digital world (texting, email, etc) so much that people aren't good at interacting with others face to face anymore (out of practice, never learned, blah blah).
And people go into checklist mode when they meet someone from an online source (job, education, hobbies, blah blah). I remember when it used to be, "Bobby, in my math class is so cute and funny." There was no, "Does Bobby have hopes to be blah when he grows up? Does he plan on going ivy or state? Does he swing dance on the weekends?"