In no particular order: Ante Up by truelyesoteric
Word Count: 9,000+
Warnings: Personal assistant Jared, Rich Jensen. Drunk Jensen. Monologuing Jensen. Not quite practical situations. This is fluff people. This also makes me happy.
Summary: Jensen owns a lot of hotels all over the world. Jared is his personal assistant who has been with him all over the world. They come to Vegas a couple times of year. This time is a little different….
I love fics about misunderstandings, if only because Jared and Jensen are so utterly oblivious and adorable in this.
This basically features businessman Jensen and PA Jared having such a camaraderie and chemistry together that their friends want to bash their skulls in when they can't see it themselves. Jensen is planning on getting married to some girl he barely knows that isn't honestly a match for him, Jared is feeling horrible since he assumes his love for Jensen is unreturned, thus where the angst and misunderstanding comes in.
For all it's angst, it's really fluffy and humor filled with a lot of the regulars we normally see acting flabbergasted at J2's airheadedness. So it's a long, fluffy, fic that features great characters and a story you can settle down with when you're feeling bad.