Id go alone the first time.. there's no pressure from someone who knowns what they are doing. That way you won't feel rushed or being watched by a critical eye or whatnot.

Don't overthink what to do. just take a walk in a nice place if you enjoy being outdoors. Maybe find a place with a nice view, or stars in the sky or some shit. Or just go the other way and chill with some ps or porn or whatever gets you goin ... music is cool too, but your head might be too much all over the place the first time to really be thinking much about it. nothing that demands too much concentration .. that will take away from it.

best advice i can give you (if youve never smoked before) is when your inhaling, chase the smoke down with some air after you take a pull. Just take a good hit, hold your breath momentarily then open your mouth and gasp in a little air then hold your breath a couple seconds after. It will make sure all the smoke in your throat and mouth that doesnt get to your lungs if forced down. Easiest way to avoid "not getting high the first time"