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Asking

Asking is better than waiting for them to tell you, since there's a number of reasons why they may not tell you.

It may slip their mind, they may think you already know, or they may assume there will be something to accommodate their requirements anyway.

If you ask, you show your willingness to accommodate their dietary restrictions and you show that you care enough to ask. This might convince someone who is hesitant to accept.

How to Ask

When cooking for a group of people, ask it right in the invitation.

As mentioned above, it shows right off the bat that you're willing to accommodate them and showing that you're a good host.

Also, by putting it in the invitation, you're asking in general. If you're afraid that asking personally might imply anything, here's your chance to avoid that.

People I know who organize foodstuffs for events that attract lots of people with lots of different food related wishes have taken to calling the collection of this "Culinary handicaps", although it might depend on the setting whether or not people enjoy a description like that.

Probably "dietary requirements" is a safer way to put it.

(I'm not sure whether this is on topic for interpersonal skills, though. It sounds more like an English Language Learners question. Or maybe a Cooking one.)

Generally it is on them to tell you, but it is nice of you to ask. Asking shows that you care about their needs and special requirements and I don't believe anyone would find it as rude or awkward or as an implication of a disease.

A good idea is to ask before hand if anyone has any dietary restrictions so you can plan food for them and not during the meeting when all the food is already prepared.

Since there is no location tag, I'll answer from a Dutch perspective. You say: "Do you have a special diet?". Simple as that.

Everyone will understand why the question is asked (the reasons you already summed up) and will also understand such things can not be seen from the outside. Nobody will take offense in this, as they are asked this same question every time the eat with strangers, whether it's in a restaurant or as a guest in peoples home.

In fact, if someone would take offense, it would be them that broke etiquette, as such a question is considered harmless, polite and expected.

Come to think of it, I should add that not asking the question might get you some raised eyebrows from people. Restaurants will normally provide the needed information in their menu's, but in a private setting you are more or less expected to ask beforehand.

is it on them to tell me about it, or do I ask them?

If I don't tell you and you don't ask me then it's up to me (as guest) to decide whether to take what I'm served.

If I don't want something I can say, "No thank you", at the time -- but some hosts/hostesses see that as a bad thing (even if that's my choice), which is awkward, so maye communicating in advance is better.

I count it as socially skilful of them if, once informed, someone remembers my dietary preference the next time without asking again.

how can I do that without implying they have i.e. health issues?

"Is there anything you don't eat?"

In most cases the guests will tell their hosts if they have any special diets that they follow. However, in the event that they don't or they forget then it's often best to ask beforehand. It's best to do this indirectly through something along the lines of:

So, is there anything you want in particular?

This will offer them a chance to suggest anything (whatever they suggest will of course be in line with their special diet). However, if they don't have anything to suggest then simply ask:

Yeah, so, is there anything you can't eat? I once cooked these big, fat barbecue ribs for my friend only to discover they were vegan and it was unbelievably awkward so since then I always remember to ask people.

This approach is pretty good because it keeps things casual and informal. It also shows the person that you're not only asking them and that you ask everyone and most importantly of all it also helps to lighten the mood with some humour which will make the exchange less awkward and tense.

I figure if I know someone well enough to be cooking for them then I know them well enough to ask if they'll actually want to eat what I'm cooking.

I usually just ask people if there's anything they don't eat. They can fill me in, or not, on the relative importance of their "don't eat" status. So, for example, I know my Jewish friend won't eat a bacon sandwich and is totally non-negotiable on that, my friend who needs a gluten-free diet won't eat bread and is non-negotiable on that, and my friend who doesn't care much for onions would prefer not to eat them but at a push can pick them out.

If someone presents a list of requirements so arduous that it's all but impossible to please them, do the best you can this time and don't invite them again.

Can't comment yet, so to clarify. If someone is such a picky eater that it's all but impossible to satisfy them, it may be that it's easier to just not bother trying. It's easy enough to choose something to satisfy a well defined restriction or preference, for example not serving bacon when my Jewish friend is visiting (knowing he not only won't eat the bacon but also won't eat anything that might have touched the bacon).

I knew someone a few years ago who had severe food allergies that seemed to constantly evolve. She couldn't have any dairy, any wheat, any seafood of any type, and it was far from rare that each visit brought a different food she was sensitive to. It was all but impossible to cook anything that worked, not least because the dish she might have eaten last time I saw her would make her physically sick this time. In a simple case where you're entertaining one or two people (in this case, the lady and her husband) it's easier to manage. If you're trying to entertain a group of people and there's one person who either can't or won't eat anything, it may get to the point where it's easier to just not invite them. I figured it went without saying that if the particular person is sufficiently important to you that you want to accommodate them no matter what then you'll accommodate them no matter what.

I think, that asking for "dietary restrictions" or whatever beforehand is not so simple, as there may be cases, which you think are perfectly normal to do and some people think they are totally normal to avoid at any cost, to the point, that they do not consider it as "restriction".

Also the list of what possible would not be welcome will be long or incomplete, probably both (hey, I would not consider to mention I would not like eating live spiders for example ... but I would not eat it)

So I would rather came with something like "I was thinking about ham and eggs and bread for this meeting, would you all like it, or should I came with something else?"

Then it is on the people to either say "yes, good with me" or say "Sorry, I do not eat anything of pigs", "I would not like eat even the eggs, as they are animal babies" or "I cannot eat bread if it contain gluten as I am allergic to it"

So now you see, that the original choise was not best for this group and considering available ingrediences (now and here) you offer something else: "And what about vegetable salad with olive oil?" and now is is all good except the lady there, which say "I would rather get it without oil at all" (as she try to loose some weigtht before season) and you say "yes, no problem, I will not add it on your plate."

Everyone is happy and you know, that you can provide that. And nobody have to solve long puzzles about living spiders, monkeys brains, mushrooms and all other possible foods, which somebody "just does not like" for any personal reason (dislikes, allergy, religion, cultural, whatever).

I will bet, that for ANY food exist at least one person, which does not want to eat it.

Some of my friends are vegans, some of my friends say "it is not food, if there is no meat in it" (and means like at least 75%) ... there are people saying, that doing steaks over "rare" should be punished by law, others like it "really, really well done" (that is just a small step under "totally charcoiled") ...

But usually even in large groups is possible to find small number of subgroups, which would like SOMETHING common for the subgroup and so it is possible prepare like 2-4 kinds of food and make everybody happy.

But IMHO is better to offer, what you can do (have acces to ingredients, have practice with and such) and ask, if it is OK with everyone (and then target the parts, which does not fit), than ask everyone, what he/she/it/... would like (as you end with as much request as are people in the party) or ask what each one does NOT like (as it results to long incomplete lists and feels awkward to many people to talk long about what everything they cannot/do not want eat. But saying "I would prefere salad without oil and just watter instead of beer" is not so hard and is easy to fullfill.)