When/How should you ask a guy out?
28 March 2021, 17:54

27F and have been crushing on a coworker for over a year. I know I know the saying... that's why I held back for so long. Well now I realized it's probably more than a crush and he's reciprocating as well. He's much older than me (mid 30s) and he seems a lot more confident than I am so I figured after the flirtatious exchanges he'd ask me out first. That never happened and now I'm coming into realization that this guy will probably never ask me out despite both of us having feelings for each other. My "friend" gave me really chilling advice saying if I don't ask him out now, there will be more options after COVID is over.... so now I'm thinking she is right and I will most likely loose chances with him if I continue to keep waiting for him to make a move. We are both in a professional setting and I know it's not the best decision, but I'm not looking to stay there for very long. Should I take my chances and ask him out? How does one do this? I've never asked anyone out before.... how would a guy feel if a girl asked him out first? Also, how do I ask him out subtly without fully raising flags like this is a date date... but more like getting to know each other? COVID is making it even harder to do just that because coffee shops are closed.

Lots of my close friends told me not to pursue it but after explaining to them that this guy is legit my ideal guy and he's one of the best people that I ever got to meet in my life; I feel like I would totally miss out if I don't try but I'm so shy, introverted and not confident but he's the complete opposite so I was hoping he'd make the first move. We've done the most cliche flirting that you see on a romantic movie like passing out sticky notes, whispering at each others ears, and starting at each others eyes like no tomorrow... but it still hasn't progressed to anywhere. Please give some advice :)

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