After briefly introducing yourself, you feel as if your date is going okay. She's interested now because you're new and different, but since you're not a party pony and don't have a talent that can be easily applied to that, it'll harder for you in the long run. You're not doomed, of course, but you'll have to try extra hard to show her that your personality is a close match for her. What you choose to talk about over diner and what you choose to order will have a huge impact on your success.
You show your reservation to the waiter and he nods, directing the two of you to a private booth for two. It's dim inside with most of the light coming from a large candle on the table. The way her face shines under the flickering light is truly enchanting. You feel like you could sit there and stare into her sky blue eyes forever.
She picks up the menu, but rather than look it over she simply stares at you. “You know what? I'm feeling adventurous. I'll let you order for me.”
“Me?” You gulp. You'd best make a wise choice. Tearing your eyes off of her, you scan the menu yourself. After some deliberation, you pick the item that you think she'll like the best. When the waiter comes back, you whisper this so as not to ruin the surprise. He raises an eyebrow, but you grin. Professionally, he writes down your order and walks off.
Pinkie Pie is folding the napkins into little origami flowers. While that's super-cute, you'd rather not let her get bored. You should strike up a conversation before the food arrives, but what should you talk about?
[Earth Pony] Make fun of the other races
Talk about how rich you are
Stand on your head and quack like a duck
Shower her with compliments