Make aggressive moves.
We're not going to offer an explicit YOLO, as that acronym is as played out as Kwame's polka dots. Seriously though, if there's ever a time to make a no-regrets move, it's when you're home for the holidays. So, implied YOLO.
You were a coward in high school. There were many opportunities to clumsily woo girls that you squandered. But you don't need that kind of shame and regret in your life now. You're an adult. You think you're a competent lover. If you say, "Hey, let's get out of here" with complete confidence, it might work out. And if it doesn't, you'll never see this person again. No risk.