2014: Wins the lottery (about 100 million after taxes lets say), immediately buys whatever he wanted like a nicer car, even some prostitutes probably.
2015: Probably will get approached by a gold digger, he will date her in spite of having never been approached first in his life.
2016-2020: Lives the most unfulfilling couple life ever, getting leached off his money, but since it's the only woman who ever said she loved him, he doesn't care. Will probably start taking drugs to cope.
2021 onward: After leeching off of him enough, she will quit him when she get bored. He will probably accumulate poor financial choices and will either kill himself or overdose.