Having a Ph.D at failing. That is to say, the person is BEYOND failure with lack of a saving grace in the eyes of others.
Often for a marginal error, lacking knowledge or logic based on a specific type of common sense or in some cases a life choice that may not be glorified by the "in" crowd.
1. Being a 40-year old virgin is a person who phails at life itself.
2. If you phail, you fail at failing and that's the worse.
3. Because you thought Master Chief would hit Smash Bros. Brawl, you phail to understand video games.
4. I asked for a hamburger and you put cheese on it when I didn't ask you to, you phail at taking orders.