Serious Eats - seriouseats.com

yup, glad to find I'm not so weird after all...
reeses: around the rim, then peel the chocolate off the top and bottom, then the PB
kit kats - nibble chocolate from all sides, then layer by layer
what messy freak doesn't eat their m&m's in color order? I eat the yucky colors first (brown, yellow).
popcorn, chips, etc all must be eaten one piece at a time... people who shove multiple pieces of popcorn in their mouths at one time should be shot.
remember the hostess butterscotch krumpets? I peel the butterscotch frosting off and eat the cake first, then butterscotch. Actually, I do this with anything that can be peeled and eaten in layers.
but the weirdest one, that people have actually commented on... I refuse to put anything in my mouth without looking at it first. Apparently this makes me weird... watch me eating a sandwich and I supposedly go cross eyed right before each bite. It's not enough that I saw the sandwich before the last bite, I must inspect each one.
No, i did not grow up with older brothers who put nasty stuff in my sandwiches.

If he's working and going to school full time my first inclination is to assume that a great deal of his eating during the day will be done in the car, at a desk, or in a hurry before whatever the next thing is... all of which requires food that is not messy and ideally could be eaten with one hand.
You can put just about anything inside a wrap sandwich, so it doesn't have to be the same ol' lunchmeat... I use them to jazz up leftovers all the time. Leftover roast beef = sliced roast beef wrap with provolone and horseradish, or beef with sliced red onion and bleu cheese. Etc. That way you aren't spending 5 extra hours a day making his lunch, and it's still fresh and yummy.
Snack-type things are great so that he can choose to have a midAM snack or combine it with lunch later, etc... if he has an office/desk/etc pack him a bag with some healthy whole grain crackers, nuts, dried fruit, etc all conveniently in little single servings (just divvy up into mini tupperwares) and a jar of peanut butter. He can use these to make yummy snacks or, if he has to, a meal... I do this for my hubby and it prevents him from running to the snack machine too often.
Apples are sometimes difficult to eat in a professional setting (midway through, must set on desk, pick up phone, rummage through folder, etc) but if you slice it in the AM and put it in a tupperware it WILL be fine in the afternoon - just keep it cold.

funny thing, I looove leftovers... I enjoy feeling like I somehow outsmarted the food gods and got two meals for the price of one. Also, I was raised eating leftovers constantly (that standard joke about "the original meal has never been found") with "smorgasboard night" at least once a week.
My hubby, on the other hand, never ate leftovers as a kid and so is completely horrified by the idea (granted, who would want to eat his mom's leftovers? But that's another post.
So I hide them and disguise them, like he's 7 years old and I'm sneaking veggies into his food. Like PP'ers, I always try to wait a full 24 hours before the transformation... enough time that the two meals don't connect in his mind.
I can turn just about anything into soup or stirfry, often with the addition of some noodles or additional veg. Quesadillas, piedine, etc... fancy words for "I smushed some leftovers between two tortillas and now you think it's like bar food." Leftover meats and veg often (read: on a weekly basis) reappear as a cold salad over some lettuce later in the week.
Case in point: Saturday night was red-cooked (soy) pot roast type thing with soba noodles, chinese cabbage, water chestnuts... meat reappeared as "steak and eggs" on Sunday morning, tonight is soba noodle bowls (add more broth) topped with shredded beef and veg, chile sauce.

use constantly: bamboo tongs, microplane, box grater, colander, mini chopper (mini food processor), wire basket for grilling, silicone baking mats and 1/4 sheet pans
why did i buy (or why did I register for): tabletop rotisserie, extra small crockpot, bagel biter.

okay, I have definitely been there, many all nighters in college. As architecture majors we were the best at not sleeping for three days (and then playing with lots of sharp exacto knives...)
Here's what you need to do: drink LOTS of water. Tons. It keeps you hoppin' cause you'll need to pee constantly. I associate peeing with waking up first thing in the AM. Time it right and you can convince yourself that you really did just roll out of bed after a long night's sleep.
Since you will presumably be working while all-night-er-ing, food that won't rub off on med school apps is key. grapes are good and can be frozen for extra fun. smoothies are a yummy way to work in those messier fruits and you can add some kind of protein and just sip that fourth meal (also, insulated or non-condensation cup very important, don't want water all over that important document).
something small and crunchy in the car - nuts or maybe wasabi peas? They will definitely keep you awake and reaching for water!
avoid beer - any alcohol actually - and caffeine. I did not take this particular piece of advice, unfortunately.
nothing warm... no comfort food here. small, cold, crunchy.

can you eat other nuts? I have some nice brittle recipes that I think i got from food network... one is hazelnut and one is sliced almonds. You could also try a sesame seed brittle, similar to the sesame seed candies.
I love the texture of peanut brittle, also the brittle part, but I don't like the whole peanuts, so I go for other-nut-brittle instead. I'll see fi I can dig them up when I get home.

When my mom made peanut brittle, she put peanut butter in the brittle candy part... I'm guessing that's not a standard thing?

kale and smoked neck in the crockpot... oddly enough, a childhood comfort food of mine, although we tended to eat it in the winter.
Tons of kale, some smoked (pork) neck or a few ham steaks if you can't find that, salt, little bit of chicken broth. Stick it in the crockpot and that kale cooks down to nothing!

cabbage and kielbasa in the crockpot... another childhood staple... cut up cabbage, kielbasa links, caraway seeds, little bit of sliced onion... great with a grainy mustard and a beer.

I actually just finished IDoF and found myself mentally editing the rules as I read. the "grandmother" rule I altered to "don't eat anything that ANYONE's grandmother wouldn't recognize" because I do eat lots that dear grandma wouldn't recognize, but someone's Greek or Indian or Japanese grandmother might.
The only one of the rules that I truly break is that I do on occasion use splenda or splenda-sweetened baked goods, which I bake myself. It's not an artificial-sweetener overload, just an occasional thing, but MP would definitely not approve.

FRUIT. seriously. You might want to try "reset"-ing your body's understanding of where the line is between "sweet" and "not sweet." try not eating anything sweetened with sugar (or artificially stuff) for a week or so. Then eat a granny smith apple or some in-season, really ripe peaches or strawberries or watermelon. Let foods that are naturally sweet in and of themselves be the "sweet" things in your diet. You can't go wrong with a piece of fruit.
And the occasional small piece of very dark, very expensive chocolate!

I am a big fan of south beach and have lost a good amount of weight with what I consider very little heartache (being a food lover).
To clear up a couple things:
1. SBD does NOT restrict carbohydrates, and you are NEVER asked to count carbs, net carbs, or any of those other silly things. The diet (although in the most succesful form it's really just a "way of eating") emphasizes food low on the glycemic index - food that your body has to work on getting to the nutrients. Good fats (unsat), protein, and fiber are all important - but again, you NEVER have to count anything.
2. Yes, for the first two weeks or so you are supposed to give up all fruit and grain products. However, it's not so much that "fruit and grains are inherently bad" but more that "most people eat lots of crap" and this is a way to wean yourself off the crap. A whole apple... good thing. a big glass of processed apple juice... all sugar, which immediately rushes to your bloodstream, causing a spike and then a big dip (when you rush for MORE food). It's all about getting off the rollercoaster of blood sugar highs and lows.
3. Atkins, for a while at least, did not restrict fat (saturated) intake and in fact pushed things like full fat bacon, cheese, etc. SBD recommends emphasis on the "good" fats found in evoo, nuts, seeds, etc and lean meats.
4. "You always have to cook." Entirely not true. Find me a restaurant in America that won't serve you a green salad with some chicken on top. Just say "no croutons." Order the grilled salmon with extra veg, no potato. It's actually very simple to eat SBD without slaving over a hot stove. It's also easy to eat SB with others who are non-SB... you aren't restricted to shakes or bars or anything that you can't find in a normal restaurant setting. I've eaten good SB friendly meals in ITALIAN joints. And no nasty frozen meals... I know they make SBD meals, bars, etc... stay away from them, seriously. That's not what eating is all about.
5. I would absolutely agree with PP's who suggested contacting a nutritionist, especially when dealing with a lot of weight or another serious medical condition. They can also give you more information - but read the SBD book first (blue cover, I think) which will give you a better understandingn of the principles behind the diet.
6. SBD does not ask you to count calories, fat, carbs, grams of anything... which is very good for everyday living. Some people ask, well then how can you lose weight? I used to have very "moody" blood sugar with lots of highs and crashing lows. I finally was eating about every 2 hours just to keep from fainting - although I tried to eat healthy snacks (fruit, granola, yogurt) I was eating WAAAY too much... my body didn't need all those calories, but my blood was telling me it needed more glucose. Not a good situation... SBD cleared up the blood sugar issues, I promise, in 2 weeks flat. I don't count grams of anything, but I have lost a lot of the weight simply due to the fact that I am only eating when i'm hungry, because my body's not addicted to sugar anymore.

In order to understand it, you really have to read the book or talk to someone, because there are a lot of misconceptions out there that can derail your BF's efforts if he falsely believes them. Good luck!

Lots of great suggestions and I picked up some tips just scrolling through.
veryculinary, as the summer is halfway over you may want to think about getting in some cooler weather crops in a month or so (depending on where you are exactly)... lettuce for sure, and beans I believe, do better in slightly cooler weather. DH and I grew lettuce this spring and the difference in the grocery bill was noticeable (we eat a lot of salad).
Use the freezer, not only for freezing large bulk-buy quantities of things, but also onesie-twosie portion leftovers. Obviously this works better with some things than others.. but soups, stews, chilis, pot roast... stick a single leftover serving in the freezer. If it means the difference between eating it two weeks from now (rather than ordering takeout) or it going bad and getting tossed... freeze it. Instant tv dinners and much better for you.
Keep snacks with you. This sounds counter-intuitive, but if you are out and about (or just at work) sometimes it's easier to go for the vending machine or deli or bakery... all of which are more expensive than the handful of roasted almonds you threw in your bag that morning. I carry a baggie of nuts, an apple, and a water bottle constantly, and it really cuts down on the "extra expense" of snacking.
Find a grocery with a bulk food aisle. Most of the ones near us don't have them anymore, and I know it might sound counter-intuitive, again, to go to Whole Foods, but ours is the only store in the area with bulk bins. Bulk Bulgur is very cheap, very easy and quick to prepare and filling and nutritious as well (also bulgur salad is a good kitchen sink for leftovers that may have otherwise gone to waste).
Careful menu planning, to echo others... make sure you are using your leftovers and not letting things go bad.
Good luck and I hope that things turn around for you and your hubby!

I know you're already thinking pasta, but what about stuffed shells? You can boil and stuff the shells, then freeze them in a single layer on a baking sheet. Once they're frozen, slide them into a big ol' freezer bag and present with a jar or two of good quality tomato sauce. This will allow the new parents some flexibility (are there just two of them that night? Make half, or the whole batch if grandparents are coming over. etc) so that they aren't heating up a casserole and then eating XYZ for three days in a row.
Also, DH figured out that they are pretty yummy heated in the micro, just one or two at a time. He didn't even put sauce on them. Throw some frozen chopped spinach into the cheese for more nutrition.

Unfortunately it really does seem like the basic skills of cooking are being lost on the younger (ie, my) generation... I am the only, and I mean ONLY person my age that I know, who has both the skills and equipment necessary to roast a whole chicken. Yes, that most basic of dinners, roast chicken, mashed potatoes, maybe some carrots or brussels sprouts roasted as well... waaaaay beyond most people my age, it seems. And I have a lot of other young married friends. It seems they are serving their DH's cold deli sandwiches for dinner (aka "cooking" or "playing Betty Crocker" as one friend puts it) or ordering out.
Now granted, I am not making Thanksgiving dinner every night of the week... but come on! Isn't this a basic skill to be learned before leaving the nest?? My parents considered basic cooking skills, as well as balancing a checkbook, two necessary things to know before leaving the house.
The other "dying skill" it seems, is the ability to use leftovers. I guess because so few people cook their meals, the concept of using that leftover chicken in a salad tomorrow night is waaaay beyond.