I'm not really certain I would be all that frustrated IRL if it took me two minutes to attempt to something difficult.
For what it's worth taking 20 is actually not the same as rolling a d20 20 times. Because of probabilities and stuff. You could get a 20 on the first roll, or not until the 100th one.
Flirting and romance are better just handled with RP. And even those are somewhat minimal in most games I play.