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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.
A housewarming gift has a narrow brief. It should suit a home the owners are still arranging, it should not add to the pile of things they have to find space for, and it should feel chosen rather than grabbed on the way over. Chocolate meets all three, which is why a hamper or a share bag tends to work better than another candle or a plant that needs looking after.
New babies and christenings bring a run of gifts aimed squarely at the child, which is lovely and also slightly misses the people doing the hard work. A chocolate gift, especially a personalised one, quietly addresses the parents and the wider family at a point when a small kindness lands well.
Thank you is the most common thing a gift has to say and the easiest to get slightly wrong. Too small and it reads as an afterthought. Too large and it puts the recipient under a strange obligation. A mid-size chocolate collection or a share bag sits in the right register for almost every version of the occasion.
If you are ordering with a printed message, keep it short and warm, and allow a little extra time for the personalisation, especially in the busy end of the year.
For an early anniversary, a first or a second say, the register is warm and unshowy. A mid-size collection, perhaps with a short printed message or the date, Lily O'Brien's Chocolates says you remembered and you made a small effort, which is precisely the tone those years call for. It is a gift between two people rather than a public statement, so restraint reads better than grandeur.