This is particularly difficult if you've been going out with your ex for a very long time. You have no idea what is cool and hip on the dating scene and you're not really sure what to wear or how to act because being yourself just seems like a ridiculous concept. What is acceptable these days? No matter how many huddles you have with your friends before (and sometimes even on) your first date, nothing can prepare you for it. It's going to be awkward, you're going to feel uncomfortable and all you're going to be able to think about is your ex and how badly you'd rather be at home watching Netflix. Or you could be pleasantly surprised and actually enjoy yourself. Who knew?