Tell him how you feel because it’s better than watching him closely and searching for signs he feels the same. It’s better than torturing yourself by rereading texts, trying to figure out whether there’s a hidden message behind his words, whether his compliments were casual or whether they meant something more, whether you’re on your way to a serious commitment or whether he is only entertaining you until he finds someone who gets him more.
Tell him how you feel because it’s better to risk rejection than to risk regret. Although it might hurt to hear he doesn’t feel the same, it will hurt even more if he walks away without ever knowing how you truly felt about him. It will hurt even more if you feel like you should’ve done more, like you should’ve spoken sooner, like you missed your only opportunity at a love story with him. You don’t want to be kicking yourself for keeping quiet. You don’t want to wonder what could’ve happen if you made another choice.
Tell him how you feel because hiding your emotions isn’t going to protect you. You could still get hurt, even if he has no clue what you’re thinking, even if he’s completely oblivious to the fact you’re interested. He could start dating someone new tomorrow — but there’s a better chance that new person will be you if you speak your mind, if you wear your heart on your sleeve, if you let your heart be seen. If you don’t tell him how you feel, he might never tell you how he feels, and you know that question has been eating you up inside.
Tell him how you feel because the timing is never going to be right. You’re always going to come up with a new excuse about why you aren’t ready. You’re always going to tell yourself tomorrow is a better day. But you don’t want to hide behind your procrastination forever. You don’t want to trick yourself into thinking there’s a right and a wrong way to do this, because as long as you speak from the heart, you’re on a good path.
Tell him how you feel because you’ve been dying to get this off your chest. You’ve been itching to get the words out of your mouth. Even though you’re terrified of his reaction, all you really want is to see that reaction, to see whether you’re on the same page, to see whether he has been pining after you for as long as you’ve been pining after him. You’re tired of questioning. You just want to know.
Tell him how you feel because you deserve the chance to move forward — or move on. You deserve to know whether it’s time to take that next step with him or whether it’s time for you to heal your heart and search for someone new.
Tell him how you feel because it’s better than leaving your heart hungry. It’s better than leaving your soul aching. It’s better than leaving your mind wondering. 
