There were a bunch of us in a town, which consisted of a little house or whatnot.  Maybe we were in a foreign coungry - I don't know.  But I was following around a wild-haired man (that looked sorta like Evel Dick on Big Brother), and I was feeling very very fond of him.  It was a comfortable love I think.  I was giving him space to talk with an older lady - his mom or grandma.  And he was summing up his love for her in a small joke (that wasn't funny, but more poemish).  He had a knife in an old green case (short katana?) and I was going to try and buy it from him.  Donna said I should ask 2 or 3 dollars for it. I ended up not wanting to push the issue for a bit and when I got to it she'd already bought it from him for me.  (My supervisor reminds me of Donna, and she said I should ask my employment to pay the $260/mo supervision cost.) 

We were piloting a ship in the water.  The co-captains and captains had to be within 60 feet of the steering column.  Donna (my aunt) had the captains hat and she said she was going to give it up and I was on my way, but an older lady called it and I said "that's okay, I've gotta go pee right now anyway."  Then I said "you might want to look, I haven't checked it in a while."  Sure enough, she was about to have to steer into a hole in the mountains underwater.  I went to pee and got sucked into a weird underwater creature.  I was fighting my way out of it when another of my comrades fell in with me and was screaming (the comrade was a multilegged almost octopus-looking thing)... I found my way to the surface of the water 'cause the ship didn't notice that I was gone.  I followed the direction they were going ~ I was skimming over the really shallow water.  I looked on the bank and saw scary-looking tribes that were frozen in motion.  Since my direction-sense was good I continued to follow where the ship was going.  I got almost to the island where the ship was surely going to be docked for the night.  The tide pulled me and my octopus-buddy straight away from the shore and I was trying to swim and trying to swim back to the shore and the water was much deeper.  My buddy was having a harder time, but finally I made it... (I don't know if the buddy made it)

I'm gonna try my hand at this, but Definately welcome more ideas!
I know what the first segment is about.  
As for the second segment... I'm afraid I'll be set back if I give up control, but eventually I'll get there?  And more forward or aggressive people are helping me out and taking control from me?  What's with the shallow water and the deep water?  Ohh... At first it's not so bad, but then just when I think I'm getting there it gets a Lot more tough, and then I reach my goal and my support system?  That part is kind of like me getting a job.  At first it wasn't so bad, then everything hit at once and I was in deep and needed a job.