What I tell my nephews: flirting is basically this – give moderately strong signals of interest with plausible deniability (for you) and outs (for her), and then be attentive for returned signs of interest and riff off of that. If she plays with you, you can ask her out.

It’s not actually that complex, any boy who plays a video game involving stealth where you move a character and the camera at the same time is more than capable of being a skilled flirt. People just aren’t taught how to speak in allusions and innuendos etc but it’s very trainable.

It takes practice. I’m actually liking the video game analogy – there is similarly an algo for “move into space, hide behind cover, anticipate enemy movements, shoot them in the head while paying attention to the entire field of battle” – it just takes practice and you will fail

The trick is to make sure that your failures are survivable. So first identify a list of things you should never do/say (ie blurt out “I love you”, “will you be my girlfriend”, anything that puts the other person on the spot) and then try a bunch of things other than that

Probably like 9 out of 10 times, you’ll end up being too vague or incoherent – but as long as you didn’t say anything outright creepy or corner her, you’ll be fine and you can live to try again another day. Do this 1000 times and you’ll get the hang of it