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homemade chicken strips, tator tot casserole (both my kids favorite), pork tenderloin with veggies, I throw in carrots and spaghetti squash in spaghetti for added veggies, grilled chicken of any kind, stir fry/Chinese/Asian chicken of any kind with rice.

Not like super heathy, but my picky 5 year old will OK pesto, zucchini noodles (any sauce) and fried rice which our family loves.

ETA: she will also eat soups and chili well; mainly chili and Italian wedding soup

It's such a hard habit to break. I find that DS is more willing to try new things when he's just a little hungry. If he's very hungry it's hopeless and everything will be terrible... It's hard to hit that perfect moment.

@Shantuck: you aren't alone! This is my biggest struggle. Will he eat tomato sauce on pasta? Sneaky chef makes a tomato sauce with a bunch of hidden veggies. I also tried zucchini noodles the other day and she ate them... I was shocked.
I will also cut sweet potatoes like fries and she will eat those. She likes hummus so I try to give her vegetables to dip because dipping is fun (she's 2 )
https://www.thesneakychef.com/products/

Get him involved in the prep of dinner, setting the table. I find DS is more willing to try something unusual if he's helped make it.

We do family meals but nights we are having something spicy or I know DS just really doesn't like I'll do a separate meal. Just keep trying as I know that DS will one night declare he doesn't like something and the next night eats it. I always make him try one bite.

In your case I'd try and make things in bigger volumes for him that you can have in the fridge a few days or freeze. Then you don't have to cook a separate meal so often.

My 5 year old has issues eating and the recommendation is usually food chaining, offering one meal with at least one item that he or she likes. I know making them try at least 2-3 bites of everything works for some kids. If it is very problematic you can go to an ot for feeding therapy.
Eta I try to make the favorite foods healthier. Shredded sweet potato or zucchini in pancakes, muffins loaded with veggies (toddler muffins), using squash in place of sauce on pizza. We have no luck with any meat so lots of hummus, bean quesadillas, peanut butter.

@skipra: going further on the foodchaining thought, it also means introducing foods that are just a little bit different than what your kid eats. It can be really lonely as a parent with a kid that has food issues...a lot of people like to tell me it's my fault for a whole host of reasons!

Say you want your kid that eats French fries to eat a baked potato. You wouldn't go from one to the other, you'd do it in steps, introducing first different French fries, like thick cut if your kid eats shoestring. Once they accept that, you do the different shaped potato patties, like those face shaped ones. Then you do tater tots. Then you try hash browns. then you try mashed potato, then the baked potato.

It can be really effective, there's a great book that I am using for my son's issues, with the support of a feeding therapist.

@skipra: Oh, thank you for that suggestion! My son will eat ketchup but is not so keen on tomato sauce, so for pizza, he likes it with white sauce, which is so shocking to me, but whatever, I will take it!

I think the first thing to do is eat what you and DH are eating with great gusto. Enjoy your own food. DH and I went through a phase where we ate a lot of entree salads and he and I would make loud noises when we ate like "MMMMM, this is SOOO good!" while DS1 ate his dinner. Sometimes it would include deconstructed pieces of things from our salad, like some of the chicken, a few bites of carrot, etc. Sometimes it would be something totally separate.

Food chaining and helping with meal prep helps too. For example, I had DS1 help out with the salads. I would chop lots of romaine into Tupperwares and ask him to help me sprinkle toppings on each one. Shredded carrots, cucumber pieces, cherry tomatoes, chunks of chicken, etc. I would snack on things while I did it, and he would try a few pieces of stuff too. He discovered he really loved croutons so when he would see us eat our salads for dinner, he'd lean over and pick some croutons out. Which is how he discovered ranch dressing or honey mustard (which we sorta picked strategically) were also tasty. Then he would sorta ask for a bite. Then he would ask for his own salad and insisted that a salad had "lettuce, cumber, cawwot, cooton, no tayto, no adocado, I don't like."

Its not like we eat salad for every meal or anything, but now when he sees us eating a salad, he'll ask for a little on his plate too. Its not this crazy foreign thing and we never pressured him about it - its just a normalized portion of someone's meal, kwim?

I add shredded zucchini or yellow squash to pretty much everything. Its virtually tasteless and gets soft when you cook it, so it just sorta melts into whatever you're cooking. I throw it in with the dry pasta when I make mac n' cheese, I put it into my sauce pot when I'm making spaghetti, etc.

There was a time when I made a big pot of marinara with all sorts of veggies (spinach, onion, peppers, celery, carrots, zucchini) and then blend it with a stick blender. THEN I would add separately cooked browned meat to the pot and that would fly. Now they don't really care about the veggies if they are soft and chopped small.

I've made a broccoli sauce for pasta that's just soft boiled broccoli, garlic, olive oil, parm cheese, and a little lemon juice (optional) blended until smooth. Its a green sauce which might be kinda fun for kids. Without the lemon juice, it tastes more like broccoli cheese soup.

We also bought a sandwich pocket maker:

http://a.co/f7dxGuY

This is a way to kinda make a pizza-type meal a little healthier. You can use whole grain bread, have your son help lay on healthier toppings, like chicken sausage or turkey pepperoni, then you can tuck in a little bit of spinach or mushroom and make a little hot pocket type meal. You can obviously also use this for other kinds of sandwiches with different kinds of meat, sauces, cheeses, etc.

My kid also really thrives on routine. So we'll say "today is soup day" and he knows that day we're having miso soup with tofu for dinner with a bowl of rice. Now he asks if its soup day because we always have a soup day during the week and its become one of his favorite meals. Its a comforting thing to him. So maybe find a soup he might like (we did Italian wedding and chicken veggie soup with rice too) and that's something you can tuck a good amount of nutrition into as the weather gets cooler.

In the same vein, I sorta use menu templates when I'm planning for the week. Like pasta, curry, soup, Mexican, leftovers, etc. There's a rhythm to our weekly meals so even when one week its Indian curry and the next week is Japanese curry and the week after that is Thai curry, its "curry day." Same with pasta - the kind might change, but its "pasta day!"

And FWIW, my brother was a NOTORIOUS picky eater. Like, he ate so few fruits and vegetables he had horrific constipation as a small child and had to have enemas regularly. Obviously, as a family we ate a varied and pretty healthy Asian diet, but he ONLY ate certain brands/flavors of certain (highly processed) things and he was like that all the way until he was like a junior or senior in high school when he started broadening his palate a bit to go out to eat with his friends. Then he went to college and it was like a switch flipped and he wanted to try everything the wide world had to offer, including food. Now he's one of the biggest gourmands I know and eats everything and enjoys fine dining as a hobby.

@looch: I don't see why not. I use shredded yellow squash when I make mac n' cheese and if you use the small holes on your grater, you can't even see them. We added extra butter, a few slices of Kraft singles, and heavy cream to our mac n' cheese because DS1 had weight gain issues as a young tot and I couldn't get enough fat into his diet!

Also, I've whipped egg whites into oatmeal without tasting it at all - that might give you a boost of protein.

The biggest hit for my 4 year old is snack dinner- which is just tiny piles of healthy-ish food we have in the fridge. Some usual additions are thawed frozen peas, baby carrots with hummus, crackers, fruit, babybel cheese, strung cheese, lunch meat turkey or salami, turkey meatballs, and black beans.

I also love the suggestion of deconstructed dinner from Dinner A Love Story: http://www.dinneralovestory.com/top-10-deconstructed-dinners/

Basically she pulls ingredients out while cooking so she only cooks once but still accommodates different tastes. When we have chili, my kids get a plate of diced tomatoes, beans, plain ground beef, and shredded cheese, all separate.