We used to do this as locals a couple times a years, but it's been 4-5 years since the last time. My wife is probably wondering what happened there. There's probably some newer options but:
Downtown: Joule Hotel, great hotel, CBD Provisions or an Italian place for dinner, Midnight Rambler is a basement speakeasy type place for good drinks and sometimes live music
Thompson Hotel, can do dinner at Monarch (about as high end as it gets in Dallas) or the sushi place, drinks or dinner at Catbird also an option, for those 2 you wouldn't even have to leave the hotel unless you want to
Lots of uptown options, ZaZa, Crescent, Stoneleigh
North of Downtown: Park Cities Hilton is a short uber to Highland Park Village, we love Bistro 31, there's some other options, it should still be lit up from Christmas and its pretty spectacular. Ladies usually love walking the shops they're all insanely $$$$. Theres a couple cocktail bars, they can get packed and with college not back probably will be with Park Cities kids still at home.
The above rec of McKinney and Grand Hotel isn't bad either, I haven't ever stayed at the hotel but downtown McKinney is awesome and very walkable, look at Harvest for dinner and theres a speakeasy called Room One Eleven, even requires a password found on their social media.
Only comedy club I've ever been to in Dallas is the Addison Improv, hotels around there will all be standard business class hotels, and while there is plenty of food and drink options, it can be hit or miss immediately nearby
