Is it bad to admit feelings to a friend?

I made a post if I should tell my friend I like him.
I guess I should not. If it is considered bad then that is hypocritical in case my friend would think so too, seeing as he's admitted feelings for me several times in the past completely out of the blue. One time it was when we had not texted in a month.
I dont tell people my feelings usually anyways. I rather play it cool and never risk making a fool of myself ever. Unfortunately that has given men the impression that I am cold so for a while I decided to date women but I have not had any luck + women thinks im cold too. I can never do anything right.
I am very confused by my friend. He's being both distant and sweet at the same time. He's acted that way before. At least one of those times in the past I brought up how we decided to date once but then it didnt go anywhere and asked him how he feels nowadays, and he said he's always had special feelings for me and that I know he does.
I dont know how I could know that though and I cant say I do.