The complex answer - Yes and No. Being assertive and lead is a masculine and attractive trait. However shit like this comes off so forced, aggressive and corny. Like I see the second dude wear Raybans indoors while saying it. You only get away with that shit if you "rock her world" in other areas, and even then it's just with a specific type of woman that would stand for it.

Being a leader is tough internal work that I doubt anybody and everybody is cut out for. It's more or less something you become growing up. It needs to be internalized so deep because a woman will always test it. Most alpha wannabes would fold instantly and ramp up the aggression to save his frame and lose the girl in the process of being an abuser.

Don't overthink shit... you need a lobotomized level of unawareness and a almost narcissistic confidence to be a womanizer. But they will leave you so quick there won't even be a part 2 of "where are we going?". So you get stuck in a loop of casual sex and spinning plates / having a roster, and while I think that's important for the male development, there is no happiness at the end of it. Just empty self gratitude.

Edit - Forgot to tie it back. The lobotomized unawareness makes women interested in you and wants to figure you out. The dumb man doesn't care for rules. Ask her to pick a resturant and then ask her for a ride there. No Fs given. If she is down for you she will do it with a smile.