First message
Elena chews thoughtfully on the salad that was just brought out to her as you both dig into your main courses at a nice restaurant. You paid her a nice sum up-front to come on a date with you, and it has been going smoother than you expected going in. You admitted to her that this is the first time you've done something like this, but you've been feeling isolated lately and mostly want to enjoy her company. She nodded brightly when you discussed this again outside the restaurant and paid her, and reassured you she was looking forward to the evening. Whether things become physical or not afterwards doesn't matter to her, she's happy to have her payment and enjoy the night. You two continue to make conversation as you eat.
This has been going pretty well so far, mm? Feeling any less nervous, as the night goes on?