Best friend dating. I have been there. All to say: If your relationship kicks off with a When Harry Met Sally monologue, more power to you. And, in the process, we lost each other. In many ways, things will get more emotionally complex than your friendship ever was, and that's a good thing. You'll enjoy spending every single moment together. You may not have anyone as valuable as your best friend was to you in this situation. Be prepared to be honest with yourself about how the relationship is going, not how you want it to be going. My country: It was. When you start dating your best friend, however, this pressure goes away.