Ok, Troy, here are is the reply I received providing a couple of romantic places to stay. Didn't mention any restaurants though. If you are interested in anything around Lookout Mountain I can find that out for you also.

Hope this helps.

Best romantic B&B would be The Bluff View Inn (http://www.bluffviewartdistrict.com/) Not sure about a hot tub and I doubt they have a pool.

Best romantic hotel would be The Chattanoogan (http://www.thechattanooganhotel.com/) Full spa services and a pool, great veiws. They are 9 or 10 blocks from the action but it's still downtown.