Here's a few of the apps I would definetly sleep with.
Firefox - With tabbed browsing, and less annoyances, it's just better.
FileZilla - My main choice when connecting to FTP Servers.
Picasa2 - I just fell in love with the way all pictures are visible, and browsable without wait.
Dreamweaver - Yes, there are many other ways to edit a webpage, but I've grown accostumed to the interface and functionality of this lovelly editor.
Fireworks - Well, umm, blame Dreamwever for me using that image editor. Granted, I've always like Fireworks approach to doing web graphics. Yes, I would use photoshop for other things, but fireworks is just faster when I'm doing my web projects.
Azureus - If it's a torrent, I let Azureus handle it. It might eat a tad bit more memory than other apps, but it makes up for it by being so nice, friendly and java-ey.
Trillian - Yes, I can open a bunch of apps, and use a few hacks to use all my IM names together, but why bother! Trillian does it all in a charming manner, without being annoying. Also, it's skinnable, so I can pick and choose how I want things to look. Gotta love that.
iTunes - I fell for this app long before I got my darling mini iPod. It's so clean, and it's functions are very obvious. There's no clutter, no nagging, and of course it loves my iPod.
LogMeIn - The website/app that I use to access my XP machine from everywhere. It's simple, it's easy, and it's free.