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In a medium bowl, mix together the jello mixes and boiling water; stir until jello is dissolved.
In a separate large bowl, beat cream cheese until smooth. Gradually beat in the milk with the cream cheese and mix until smooth.
Pour in hot jello mixture with the cream cheese and stir until completely incorporated. Add the can of crushed pineapple and mix well.
Place bowl in the fridge for 20-30 minutes or until mixture starts to thicken.
Remove from fridge and fold in Cool Whip and place back in the fridge; let chill for 2-3 hours before serving.
If desired, top each serving with whipped cream and sliced strawberries.