I still do sit-ups four mornings a week, push ups two mornings and run everyday, unless we are up at our house in the mountain. I'm at 220 lbs. now, I got up to 230 lbs. last summer and I didn't like how it effected my physical activity. Still about forty pounds overweight.

I will go with number one. I have fantasized about eating until I pass out.

I have enjoyed the most in my modest gain, is the mirror! I love looking at my larger belly and butt.

Good luck with your gaining quest. I'm following you now as well. I wish I had the courage to do the same thing! Again, best wishes and enjoy yourself!

Some challenges might be fun. Order pizza and have a time "contest" to see how much you could eat. How many ice cream cones can you eat in a day. Anything like that would be really fun.

I'm not on a budget and just casually gaining, as someone mentioned on this thread, pasta. I lot of super market chains have the boxed macaroni and cheese, which sell for a $1.00 and even less, makes almost a family size portion. I binge on it every so often to feel really stuffed, you might try it.

I think it is "do able". It depends on your age, metabolism, etc. I have gained five pounds in two days. But I'm old, so I gain very easily.
Yes you would look like a fat guy.

I can relate. I have been a subtle encourager of my wife weight gain. She's not happy being overweight and I try to me supportive.
Since I retired from the military reserves and no longer have to watch my weight, I have been steadily gaining and enjoying my growing waist and butt. I love the view in the mirror of my pot belly bulging over my briefs, someday, I will have the courage to totally let go and get huge.

I would include social/family/work related reason for "can't gain". I would love to let go, but two of the three above keep me in check.

My wife is a number 1, I'm afraid. I am currently a number 3 or 4. Fantasy, 5 or 6. Great stream.