Numerous other places have detailed the activities that Brucie likes, so I won't duplicate that information here.
I will point out that if you're trying to have multiple events with Brucie in the same outing (i.e., bowling, eating, show), the "helicopter" and "boating" events are impossible to link up in this way. When you arrive at Brucie's map marker, you're immediately placed into the boat or heli, and Brucie returns home upon landing the craft, allowing no chance to link these events with other activities.
Also, winning one of Brucie's street races or delivering one of his "exotic export" cars will also improve his like factor by one percentage point (and may increase respect as well--mine is at 100 already, so I can't verify).