A skirt-chaser is a man who keeps trying to have sexual relationships with many different women. You use it to show disapproval: you think he treats women as a sport, not as people. It names the person, not one evening. Skirt here is old, rather rude slang for a woman, taken from the piece of clothing — a way of talking about women as if the dress were the person. The whole word is dated and a bit newspaper-ish. Younger speakers are more likely to call someone a player, or simply say he is creepy or unfaithful. It is not a compliment, and it is not a cute joke.

拈花惹草的男人、到處獵豔的人（貶義、偏過時。skirt 用裙子代稱女性，語氣輕慢）