Skip it.

[Minako would have told him to go for it, but Jim? Nope. He's all about situations where he can provide for his date and make her feel safe with him. That can't be done if he's falling on his ass over and over.]

I think the joint lessons are the sort of thing you go for when you're completely committed to each other. Make sure you've got someplace warm you can go to after the hike. A coffee shop if you want to play it safe, her place if you're going for another base.