Anniversaries come in a range of sizes, and a gift that fits a first year rarely fits a fortieth. Chocolate scales neatly across all of them, provided you match the collection and its personalisation to the milestone you are actually marking.
For the mid-range milestones, a tenth or a twentieth, the occasion earns a fuller collection. These are the anniversaries people tend to mark with a dinner or a small gathering, and a larger box suits both the moment and the room. Personalisation with the year or a couple's names lifts it from a nice box to a keepsake of a specific date.
A hamper also solves the group-gift problem neatly. When a whole office contributes, the gift needs to feel worth the collection taken up for it, and a full hamper looks the part without anyone having to organise something elaborate. One order, one generous box, and the maths of who gave what disappears into a single considered present.
One honest point that applies to any recipient. If he asks about ingredients or dietary suitability, point him to the published product information rather than reassuring him yourself.
Choose a chocolate made with care, present it simply, order in good time, and your favours will do exactly what they should. They will say thank you, look the part on the table, and quietly make it home in a handful of pockets.
What lifts either above a last-minute grab is what is inside and where it comes from.
Lily O'Brien's chocolate O'Brien's has handcrafted its chocolates in Newbridge, Co. Kildare since Mary Ann O'Brien started the brand in 1992, so a hamper carries a bit of provenance you can mention as you hand it over. A gift with a story behind it always feels more considered than one without.