"Obviously, you've never seen a woman skydiving in a hoop skirt"

This quote is most likely meant to be humorous, as it is an unlikely scenario. It indicates that the speaker has seen something that is not typical, and that the person they are speaking to has not. It is most likely implied to be a spirited jab at the person they are talking to, as if to state that they have not seen or experienced as much as the speaker has. The quote also indicates that the speaker is open to new experiences and is not afraid to try something that is out of the ordinary. It might also be analyzed as an obstacle to the person they are talking to, to attempt something brand-new and out of the ordinary. In general, this quote is likely suggested to be humorous and to challenge the individual it is directed at to attempt something new.