Should I ask this guy out again?

So a guy at work has been flirting with me for months. He's shy, and I'm older than him. He'd do all the typical flirting stuff... but never made a move to ask me out. I finally asked him out for a drink, and he said he'd like to go. He was visibly nervous, and blushed. The day of... he called me and canceled. He told me I caught him off guard but he asked me if I was going to the work party. I could tell he felt bad because he asked me if my wknd was ok. After this incident, he continued to flirt... and still does. He blushes more now!

I can tell he's still interested. He mentioned yet another work party that I should go to next month. He shows up to help me out at work, and I catch him staring and smiling at me. Should I ask him out again? I just don't think he will do it.


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  • I'd just drop it. He's a coworker, which is already bad enough, and the ball is really in his court. He knows you're interested. He cancelled so it needs to be up to him to reschedule.