Pinkie Pie: Um, so… what can I do to help? Not much I can think of besides chatting…
Applejack: Keep watch in the ballroom in case our "main event" heads there and Ah can't follow. Maybe use Streetwise to ask the nobles about the Prince.
Pinkie Pie: Can do!
DM: Just remember, you don't have your bonus since this isn't Ponyville.
Pinkie Pie: I got it, I got it! <roll> 25!
DM: Hmmm… On the surface, the nobles have nothing but nice things to say about Blueblood. He's charitable, he has a keen eye for fine art, yadda yadda yadda… But one or two ponies open up and describe him as rather reclusive. Despite all his public work, the details of his private life are something of a mystery.
Twilight Sparkle: Could I ask Princess Celestia about her nephew?
DM: Sure, but she will reply,
Princess Celestia: What about him? That's an odd thing to ask out of the blue. I didn't know you two were acquainted.
Twilight Sparkle: Ah. Well. Maybe I'll just not… ask… then…
DM: Oh, wait, so you didn't actually ask that?
Twilight Sparkle: Nope. Nope nope nope. There are two scenarios in my head. One, Celestia already knows and she just hasn't brought it up yet. Two, she doesn't know and she's gonna be even more upset with us. Either way, my plan is to basically buy Rarity time to woo the Prince before Celestia can raise an objection.
DM: By… just not talking about it?
Twilight Sparkle: Yep. Yep yep yep.
Rarity: I will make my move, then. I won't approach Blueblood directly, but "admire" some rose bushes nearby and see if he approaches me.
Applejack: Do I have line of sight to that position?
DM: You do.
Applejack: Alright. Places, everypony. It's showtime.