Streekgeek-
(from the Merriam-Webster dictionary)
blissful (adjective):
1: full of, marked by, or causing bliss
2: happily benighted <blissful ignorance>
Which brings us to answer the philosophical question, as well.
benighted (adjective):
1: overtaken by darkness or night
2: existing in a state of intellectual, moral or social darkness: unenlightened
[example: the poor benighted souls who do not know the joys of reading]
“Ignorance is bliss” does not mean that the ignorant are blissful in the first definition. It does not mean that they experience “complete happiness” (which is the definition of bliss). It means that they are happily unconcerned with their problems because they are simply unaware of them.
Would you say that a person who is suffering from cancer but does not know it is experiencing complete happiness?
Both of the individuals you describe are in a position either to experience complete happiness or not. This is a matter of personality and perspective. If the question was whether complete happiness which is founded on ignorance of one’s true situation can be considered complete happiness, I think there is little doubt that this happiness is fool’s gold.
If the question was simply who is having more fun right now, I suppose that could be the ignorant and blissful individual. However, I would hardly consider that a philosophical question.