Personally I tend too switch off between approaches, which I find helps keep it fun. I think of the approaches sort of like:
1) the marathon: set a lofty stuffing goal, and pursue it throughout the day/evening. X number of calories, Y donuts, Z menu items, whatever. Avoid discomfort and boredom through a drawn out process full of a variety of foods.
2) sprinting: set a lofty stuffing goal and get it down FAST. Overcome discomfort and boredom by consuming thousands of calories before they set in (question your life choices amidst stomach cramps shortly after). I tend to prefer something drinkable for this--melted ice cream, half and half, etc.
3) Absent minded: do something else (e.g. movie or video games) and just eat freely without setting a goal--the key is to occupy your attention as much as possible to minimize your ability to check in on how much you've eaten. Snacks/bite size things are ideal, e.g. donut holes. Then when you're feeling done, marvel at how much you put away without even realizing it! And of course... there will be so little left in the containers that you might as well just finish it... and then you can head to bed topped off and content
4) the daily-life-secret: incorporate a mini-stuffing into some small window of time or privacy as you go about your day. For example, a travel mug full of regular latte and a travel mug full of breve or coffee+heavy cream look the same from the outside