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The last two is when Robins in kitchen. Talk to them and click "Talk to Robin". The progression 3 option will give you one images which is the "Make Robin a special 'milkshake' ". The other picture is from the "Affection" tab, and its the Progression Level 3 option, which is "Fantasise about Robin"

So for the first two, you have to talk to Robin while they're in the living room. Under the "Affection" tab, both scenes will be unlocked from the Progression 1 and Progression 2 options which are "Watch a show with Robin" and "Compliment Robin's outfit"

I don't think there was any special interactions in his room, other than walking in on him. What images are you missing? I have them all so I might be able to help guide you in the right direction