2,245. Flirting vs. Dating

Hilchos Issurei Biah 21:2

One who participates in any of the aforementioned activities is considered likely to participate in prohibited sexual intimacy. It is prohibited to gesture to or to wink at one of the forbidden relations, to joke with her or to act lightheaded with her; it is even prohibited to smell her perfume or to stare at her beauty. One who intentionally does any of these things is subject to stripes for acting rebelliously. One who looks even at a woman’s pinky with the intention of deriving pleasure is considered as if he looked at her private places. It is prohibited even to listen to the voice or look at the hair of one of the forbidden relations.

Hilchos Issurei Biah 21:3

The aforementioned things are likewise prohibited vis-à-vis women with whom intimacy is forbidden based on a Torah prohibition. It is permitted to look at an unmarried woman’s face, whether she’s a virgin or has previously been intimate, in order to determine if one finds her attractive in order to marry her. This involves no prohibition – in fact, it’s proper to do so long as one doesn’t look at her in a promiscuous fashion. Job 31:1 tells us, “I made a covenant with my eyes not to gaze at a maiden.”