1. It was burgers and milkshakes, then a movie, because in Jon's world, that's the only way to do a first date.
2. He insisted on paying, regardless who had the bigger trust fund.
3. After determining that, yes, he was going to hold open every door and pull out every chair for her, she started racing him for doors. He still won, but she made him work for it.
4. She got him to blush at least a dozen times.
5. It ended with a pleasant, mostly chaste, kiss good night, but there will probably be a second date if she's up for it.
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