I have come to understand that in order to get what you want from women and life in general, you need to be assertive and pursue it with all you have. Assertiveness being the balance between passivity and aggressiveness. The thing is, I am assertive when it comes to platonic actions, such as not being afraid to ask for a different dish at a restaurant, conveying to a friend that they annoyed me and should not repeat the same action in the future, or just walking up to strangers because I wanted to see what they are like. Making new friends isn't an issue anymore. I have actually been told by numerous men and women that I am a personable, social man. But I keep repeating the same mistake of being too passive when it comes to pursuing a woman sexually. I take too long, and the woman gets bored, but I don’t know how to go about capitalizing on my sexual interests without seeming too pushy. Seddit, how do I go about fixing this? Do I just go all out trying to escalate every chance I get?

Note: I have a friend who is able to hook up with women fairly easily, even ones in relationships. This is not my goal, but it amazes me as to how even after a woman tells him “no, I have a boyfriend” he just pulls them over anyway and makes out with them like it is no problem at all, them loving it in the process. I don’t get how this works. Enlighten me, please.

TL;DR : look at the title.