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1. I always think of the only one I know which is Holliday Grainger. It seems to work on her, much like many celeb names "work" because they are like a brand and less like a person's actual name.
2. To me, it has an old Hollywood vibe, like Judy Holliday. I also googled it and got this dude: https://en.wikipedia.org/wiki/Holliday_Bickerstaffe_Kendall.
3. Personally, I like it in theory but not in person so I give it a 4 or 5 out of 10.
4. That's a good question. Perhaps Ginger, Fable, Evergreen, Friday, September.
5. I would use it fictionally.