"Will she judge me if I'm nervous?"
No. I will barely register it, and never unkindly. Nerves at a first meeting are information that you care, nothing more. They outlast approximately one drink.
"What if I'm inexperienced?"
Welcome, when approached with honesty and care. What makes an evening good is attention rather than experience, and attention needs no résumé.
"Will it feel transactional?"
The arrangements exist precisely so the evening does not. Everything practical is settled before we meet; what is left in the room is company, conversation and time.
"Is this discreet?"
Yes, in both directions, permanently. No public phone number, no tracking here, and no detail of you shared, the same privacy I keep for myself.