One of the issues identified (ironically by Google Chairman Eric Schmidt in his new book) is the fact that a strong sense of group comraderie seems far more important in the younger generations than in the older. When I was a bit younger in web 1.0 2000 I attended movies with my friends, went to theme parks …I even braved entering a bar (though I didn’t drink).
I think as people age and get family the ability to do those single associated activities together goes away and older people suffer for it at work. The younger generation seem them as parent types and don’t want to include them in social gatherings and for those interviewing at a company it’s hard for the younger set to see them as yet another person that they can’t have fun with (or so they believe).
As for solutions I’m working on something that may bridge the gap but I can’t say much more on it.