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I am making myself eat every few hours!

I was 288 and I went down to 136.

Up to 152 now.  I am a 5'10 41 year old male........I have never gone below 2500 calories a day.

The problem I have is that I only gain weight when I eat junk!

I had cholesterol issues in the past so it is very hard for me to load up on donuts and burgers etc. as I don't want to go back on meds!

Any advice?

eat more

ur male, u should be starting at 3000 to gain

Congratulations on the weight gain. So here are some alternatives to junk to keep the cholesterol issues in check while continuing to gain.

(and yes, 3000 calories a day or more is best)

So, you do want to avoid transfats and hydrogenated oils, but all other oils, including saturated, will be good for your heart and your weight gain.

You also want to avoid a lot of processed sugars as these turn out to play a bigger part in bad cholesterol counts than fats do. Which means avoid low-fat options as food processors up the sugars hugely to compensate for lower fat. Fruits are fine in whatever quantity you want.

Coconut oil -- excellent choice -- cook with it wherever possible. Add flax oil or hemp seed oil on steamed veggies after they're cooked, or salads. Lots and lots of nuts and nut butters on anything and everything. It's about 120 calories for each tbsp of oil you add so that can really keep your calorie count up to where it needs to be. It's about 110 calories for every 10 or so nuts you can consume too!

They've been all over the animal fats for a while now, but it turns out they aren't enemy number one in heart disease development. Which means, get whole milk, full-fat yogurts (no added or synthetic sugars, but fruit versions o.k.) and cheeses and enjoy.

Butter (saturated fat) is better than margarine (hydrogenated fat). Load up baked potatoes with sour cream, butter and cheese.

Nothing wrong with making your own pizza at home (just buy a frozen pizza shell). Just pick a jarred pizza sauce that is low in (or has no) added sugars.

Hope these ideas get you started. Best of luck.