יום אהבה שמח
2) Can one rationally explain the behavior or ritual apart from the gentile holiday or event?
3) If there are idolatrous origins, have they disappeared?
4) Are the activities actually consistent with Jewish tradition?
In the case of Valentine’s Day, one may certainly argue that the rituals performed today do meet these criteria. Sending cards and chocolates and giving gifts can be explained as rational expressions of love and appreciation independent of possible Christian roots. In addition, these Christian roots have been questioned by scholars, as well as the Catholic church.The academic work of Oruch and other scholars further proves that Valentine’s Day is not derived from the pagan holiday Lupercalia. Finally, the desire to express love and to offer gifts as a symbol of those feeling is certainly in line with Jewish tradition and values. The idea of a special day set aside to encourage coupledom is also well rooted in the Jewish tradition: Tu B’Av, the 15th day of the Jewish month of Av, was an ancient day of matchmaking that has experienced something of a revival in modern times.While it does not represent every opinion in Jewish literature, the source from the Rama does provide the most salient criteria for making this decision according to Jewish law and it is the basis upon which many rabbis allow Jewish participation in Valentine’s Day rituals.”
The full text of the article can be found here: http://www.myjewishlearning.com/holidays/About_Holidays/Non-Jewish_Holidays/Valentines_Day.shtml