(a face) like a wet weekend = a boring, disappointing time (or, of a person – looking miserable)
e.g. I am going on a family holiday but unfortunately, my cousin is coming and he has had a face like a wet weekend since his girlfriend ended their relationship.
This primarily British idiom, used since around 2000, alludes to the misery and disappointment of when weekend plans are spoiled by rainy weather. It applies to a situation or person. The idiom is often used as “like a wet weekend in…” and the name of one of many places is added. Modern usage: “It is not easy being seen as the corporate grim reaper, the man with a … face like a wet weekend. Insolvency practitioners are not the sort of people generally welcomed with unbridled enthusiasm and a beaming smile” – Scotsman newspaper.

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