My boss wants to take my wife on a date

What kind of spineless pussy are you? Fuck no she don't go. The mere mention of it from either of you is pathetic! Who the fuck does your boss think he is to even ask?

Yes she should go. But you should make him wait until the third date to fuck her.

My wife boss fucks her almost daily

If you trust her, let her go.
She'll probably have fun.
Women enjoy the attention.

I don't see what the big deal is.
This time of the year, my wife will attend numerous Christmas Parties with single male co-workers, male friends or some of her dad's golf buddies.

You should agree only if you get something out of it.

Agree. Tell your boss she'll blow and fuck him but you want a raise and bonus.
Tell your wife to suck and blow him but don't say anything about the raise and bonus. .

My wife and I have been married 22 years and together 26. We have a long time mutual friend that's very successful in his career but makes poor choices in the women department.
To this day, my wife still looks stunning in a cocktail dress or formal dress she wore back in her college days.
Around 10 years ago, my friend was getting an award from his work but didn't have a date to attend the banquet with. My wife offered to accompany him.
Since then, she'll attend his annual holiday banquet and she'll travel to their awards banquet in July. The awards banquets are usually held at a major city like NY, Miami, Houston or Nashville.

My boss lost his wife to cancer a few years ago. The holidays are very depressing for him because his kids live out of state and only visit for a few days. A tradition he and his late wife did was have attend a dinner at the local country club with his golf buddies and their wives. He wasn't planning on attending alone the first year but I agreed to go with him. We did and had a great time. He's a kind guy and said he will never date again but since then we started going out a few times a month. Just dinner & a movie or a weekend trip.
My husband doesn't mind.

Yes. And they should discuss an arrangement