This is something I've always had issues with. I would have occasions where I've tried toning it down to the point where women claim they thought I was just being friendly. I've occasionally used "someone's been doing their squats" on dating apps to try to be subtle when complmenting their curves which I assume is still creepy? Or I'd offer a bracelet to a woman at a rave while we're in the middle of a convo and be like "I forgot to tell you I come with the bracelet" and not let go of it for a split second which once got a light laugh as a reaction but apparently that's also creepy?

Most people on reddit have told me it's not scripted and flirting just comes naturally on the spot but for some reason with me it doesn't always come naturally and I just run out of things to talk about. maybe it's because I overthink everything.

How did you guys overcome your awkwardness and make it more natural and appealing? Does it just depend on the girl, how you look or how you say things? also curious what women have to say. for whatever reason it's difficult to draw the line between flirty creepy and funny sometimes.

Ultimately I want to get better at escalating things into something further, like a kiss, a date or a hookup.