Is the speaker really saying "let's see what"? Please check the script.

Are pelicans easily witnessed in the United States?

In North America, wild pelicans live mostly near the Atlantic Ocean and Pacific Ocean. In the United States, American White Pelicans can be found in the north-central and western parts of the country. Living in groups called colonies, where they are depends on the time of year and their migration pattern. Generally, it is common to find them along coasts in the wintertime.

What's the main difference between a "gem" and a "jewel?"

Technically, a "jewel" is a refined stone. Jewels are made from gemstones! Quite often a jewel is referred to by its type of gemstone. A "gem" is an unrefined, unprocessed stone. However! "Gem" is also often used to refer to a refined precious stone. Ex: I'm getting this gem converted into a jewel. Ex: Diamonds are the most beautiful gems.

What does "win over someone" mean?

To "win someone over" in this case means to gain someone's affection or make them like you. It can also mean to persuade someone into agreeing with you or allowing you to do something. Ex: I don't normally like dogs but this dog has won me over. Ex: The lawyer won over the judge's approval and won the case.

Why did he used subjunctive here?

The subjunctive mood is used in this case because he is discussing something which may or not happen, but that he hopes will happen. The subjunctive mood is often used to express a hypothetical situation or pose and idea that someone wishes could happen. In this case he is asking hypothetically whether it would be okay to ask her out, and so asking in the subjunctive mood is a way for him to not ask her directly and feel less rejected if she says no.

What does "skeptical" mean? Does it include a negative nuance?

To be skeptical means to be suspicious or doubtful about someone or something, to not be fully trusting. Ex: I am skeptical about whether this solution will be effective. Ex: Don't be so skeptical about the vaccine! It's backed by science.