According to a spokesperson for the Archdiocese of New York , Ash Wednesday should come before Valentine's Day. Period. Fortunately, the spokesperson says that that doesn't mean you have to abstain from chocolate hearts altogether this year. You can still do nice things for your partner on Wednesday; it's just that anything too extravagant won't be in keeping with the spirit of Ash Wednesday. If you were hoping to go all out this V-Day and observe Lent to the letter, the spokesperson says you can just scoot your fancy dinner or gift exchange to the night before.