We've all been warned, yet we all have likely done it at some point. Dating your best friend can be the most comfortable feeling in the world because you end up being able to share everything with them, but if you end up finding yourself not ready to share everything...well, that's where the heartbreak may settle in. It's tough to admit when you want separate lives because that means ending the relationship, and for the folks out there who don't quite have the skills to stay friends, you end up losing your best friend too. And that sucks.