Two is a couple, three is a crowd..
But let us assume that you have a real crowd to please, maybe a dozen or more people.
1. The season
This is really easy. In the warm season, even if the day is cool, you can serve any dessert that people associate with summer. Trifle is usually a huge crowd pleaser, with the kids being attracted by the jelly, the men by the sponge cake, and the women by the innocence of the dessert (surely a homely dessert like trifle is actually good for you?). Alternatively, get five or more different kinds of fruits, chop them up but keep separate, and then serve the bowls of fruit with cream, ice-cream and fresh mint leaves. Everyone can then assemble their own fruit salad and the dieters can stick with a sliver of watermelon.
Ice cream may sound boring, but you can make it interesting by serving plain vanilla, but with a whole bunch of add-ons that every person can decide for themselves to eat or leave. These can include the usual chopped nuts, thousand and ones, and chocolate vermicelli but also fresh berries, sliced fruit, sponge fingers with apricot brandy for drizzle, cherry preserve, etc.
In winter, it must be a warm dessert. It is hard to bake one big dessert that will serve 12 or more people, but again you can bake two or more sponge cakes and when they get out of the oven, serve it immediately with a selection of fruit preserves, flavoured custard, warm brandy (or brandy sauce), buttered coconut spread, etc. Fruit cake (with more than just raisins) served with hot butter sauce seem to please most people, but one must concede that it is a lot of work.
2. The occasion
An occasion where you have a mix of adults and kids allows you to make something simple because kids usually do not like fancy desserts. If you have only adults, you can shoot for something more elaborate like a Pavlova.
Try to determine beforehand whether anybody has any allergies or intolerances. Most desserts use dairy or wheat flour, and many people can not eat those products. This is also a good reason why you should try to serve something basic and then allow guests to choose from add-ons.
If the crowd is the local nursery school you can pretty much get away with anything – and if it actually flopped in the making the kids just seem to love it more. Serving wedding cake at a christening is also not quite the thing, so do try to make the dessert fitting to the occasion.
3. The presentation
You can really serve the most simple of desserts and have people talk about it afterwards with awe and envy if you get the presentation right. In summer, decorate the dishes with fresh edible flowers like nasturtium or rose. Fresh sprigs of mint go with almost anything and smell delicious. Go for colour, excitement and contrast when choosing the bowls and the serving platters. At night, use candles.
In winter, coffee beans and cinnamon sticks can be used to decorate a hot dessert and to send a subliminal message of cosiness. Hot desserts served at the same time as steaming jug of coffee also seem to be more inviting. A swirl of chocolate sauce on a plate really makes a difference disproportionate to the time it takes to do it.
Finally, if somebody does not want dessert, please leave them be! You can’t please everyone and sometimes a person really has had enough.