What to do? This holiday is a little frivolous, but there are some things to be had. This quest will ultimately reward you with a suit or dress of three colors each and it fairly simple. The key lies in the gifts though, that is where most of the ""real"" loot is.

Firstly, you need to buy a https://vanillawowdb.com/?item=21829 perfume bottle and a https://vanillawowdb.com/?item=21833 cologne bottle as well as https://vanillawowdb.com/?item=21815 love tokens. You give the tokens to NPCs in exchange for Pledges/Gifts of Adoration and gives you a 60-minute https://vanillawowdb.com/?spell=26680 Adored debuff for 60 minutes. Which NPCs you can give tokens to depend on what you are wearing. Cologne will allow you to give to female NPCs, and perfume for male NPCs. Your own character gender doesn't matter. The pledge/gift is a box that contains many things and if you get pledges/gifts while you have a debuff then you only get the gift collection items. You should a guaranteed pledge/gift if you aren't Adored, but that can change.

The pledge/gift will contain any one of three types of gift collection items and some other random items. Most of silly but what you want to pay attention to is https://vanillawowdb.com/?item=22259 Unbestowed Friendship Bracelets. You may continue to give tokens to NPCs, but doing so means your pledges will only have gift collection items or one of the rarities and you run the risk of being https://vanillawowdb.com/?spell=26898 heartbroken. That debuff will not allow you to give love tokens for 60 minutes, unless someone is able to use one of their unbestowed friendship rings on you. This will rid the Heartbroken but not the Adored.

To acquire the collections you need 15 items, each city has 3 items and you need to bundle 5 of each of the 3 item types into gift collections. Then you bundle each of the 3 city collections into a faction collection. And those are pledges of loyalty, cards, and a gift. While it may seem random there is some method to the madness. Depending on who you get your pledges from increases the chances you will get certain items. I think they chance the chances every year but you should pay attention to the three pledgees.

1. Female Guards
2. Male Guards
3. Non-Guards

Non-guards will always yield gift items and give gifts of adorations, the guards will give pledges of adoration and swap between pledges of loyalty and cards but they will have a preference. It is tricky in Darnassus and Undercity, where all the guards are all female or all male respectively. But as I have seen there is an equal chance to get cards or pledges of loyalty. And in addition there is always a chance you will get one of following rarities. It should be assumed all pledges/gifts will average around 1% - 3% to receive one of these in addition to its usual contents.

https://vanillawowdb.com/?item=22279 Lovely Black Dress
https://vanillawowdb.com/?item=22235 Truesilver Shafted Arrow
https://vanillawowdb.com/?item=34480 Romantic Picnic Basket

NOTE : Pledges/Gifts of Adoration are UNBOUND so you can be free to sell/trade them with other toons or fellow players and maintain the rarities. Once you take stuff out of them they are BoP, with the exception of the black dress.

This is an optional prequest for https://vanillawowdb.com/?quest=8903 Dangerous Love designed to get you to go to Stormwind.

There are in fact three quests called Dearest Colara, starting in https://vanillawowdb.com/?quest=8897 Stormwind, https://vanillawowdb.com/?quest=8898 Ironforge, and https://vanillawowdb.com/?quest=8899 Darnassus. Accepting one of them will cause the other two to become unavailable--there's no way to do all three in the same year.