Would you believe me if I told you that weight gain is actually a fetish in some people?
Anyway, to your case, I will suggest starting off slow, like pushing yourself to eat a little bit more i.e. when you eat your meal, but do NOT stuff yourself because if so chances are you'll vomit everything. Just keep it under control. Also, you may put off a little your exercises and focus more on eating, so move as little as possible to gain faster. Being a Christmas period, what could be nicer than sitting in your warm house enjoying eating your turkey (let's say) and watching the snow fall? Keep in mind that after a big meal, you should best sleep, so it won't be burned (I think that's why the say "don't eat much at night). And try to skip breakfast because it raises your metabolism. Sleeping it off gains you weight much faster, After a couple of weeks, you will even be able to eat thrice what you were eating before! Gaining 30 pounds in a month is quite a goal for a skinny guy, so I guess you'll be there at February.
About fat foods, don't overdo it. You can eat once a week, but if you do it every way, you'll gain weight faster, but the unhealthy way. Don't bother with cholesterol. What JPL said, eat foods high in nutrition and stuff and healthy foods in larger amounts. Fat food may work as a "boost".
So there you have it. Again, don't overdo it, because if you get mad with it you'll wake up one day weighing 200 lbs and I guess you won't be satisfied! 8)
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