I got it second try, but I noticed he always picked whatever I had last picked. Dunno if he does that with anyone else. First play through I picked rock and won. Then I picked scissors and he picked rock. Then I picked paper and he picked scissors. Second play through I picked rock and he picked paper, so I picked paper and he picked rock. Then knowing he'd pick paper I picked scissors and won.
Anyone else have him pick whatever you last picked? Did it all 4 times for me.