I'm kinda going through this right now. I feel like I've let him know that I'm interested because we flirt with each other all the time, not in a sleazy way but it's very obvious that we like each other. But he's not stepping up in the sense that things aren't moving past flirting stage Shrugs, I don't know what else to do. I can't show interest any other way outside of holding up a big sign Honestly I feel like there's nothing else we can do besides dress nicely, light flirting or showing some signs of interest, smiling, etc. You feel like men are too shy now or have been hurt too much to ask women out anymore?