Well, haha, this brings back memories when I was still in school. I wax my own eyebrows, it's painful but so much easier than plucking. I don't think the legs would be very bad but this is coming from someone who has actually waxed their arms (OUCH!). Just always soothe it with aloe or a soothing lotion afterward.
Oh and I'd definitely get waxed a few days before you're supposed to see him so you don't have that ugly red inflamed skin.
Edited to add: If you bleed bad or have sensitive skin, apply a powder to the area before waxing.