Jump to navigation. We asked dating expert Marni Battista for her thoughts on what women can do to redress this imbalance if they're thinking "should I ask him out? Throughout dating literature and countless conversations amongst single women, it seems to be the general rule of thumb that men should be the initiators of every step of the dating process - from the first conversation, to the first date , to the first kiss and so on. Not only that, but we feel as if the act of blatantly asking out a man will cause us to appear desperate and send the wrong message. However, there are ways to take action without foregoing your feminine energy. Rather than charging up to a cute man at a bar and asking him out up front, use your feminine wiles to get the ball rolling.