Don’t tell him. It’s not the woman’s place to chase a man — and telling him you love him 😯 when he’s never even asked you out, is doing exactly that. 😕 If a man is interested in you, he’ll ask you out! And if by the time he’s in his mid-thirties, as you and your friend are, he hasn’t asked you out, chances are that he doesn’t see you as a girlfriend type. You can try and change that, but you’re going to have to change your behavior. Stop being his friend and stop acting like his friend. Instead, act like a woman who’s interested in him by flirting with him! 😉 If you change your behavior, maybe he’ll change his, and if he doesn’t, look elsewhere for a date.