As May approached her late teens, her family saw it was the time for her to be married. Phoebe Hearst, who was a close friend of her mother, funded May's extravagant debutante ball. She was 'brought out' in Washington. May was considered a great beauty with a petite figure, blue eyes and long fair hair attracting several suitors who courted her. The rejection of several marriage proposals frustrated her family. She was bought out again into Newport society in the hopes of finding a husband. May fell in love during this period and became engaged, but it was broken off. May plunged into depression, and it was around this time that her health seriously deteriorated.