I am currently 19 years old and in college. My boyfriend and I wanted to go out for dinner and stay in a hotel for the Valentine’s Day. My anxieties get in the way of asking. How should I go about asking my parent?

The fact that you are an adult and yet feel the need to seek your parent's permission indicates to me that you are not comfortable doing what you wish to seek permission for.

I am not aware of your culture's expectations around this kind of behavior, but I wouldn't suggest you do it..