Chelsea's Worst Match

1 of 7
Are You There, Chelsea?
Chelsea's Worst Match
Chelsea and Sloane's high school boyfriend
2 of 7
Are You There, Chelsea?
Chelsea's Worst Match
Chelsea and the virgin Christian rock star
3 of 7
Chelsea
Chelsea's Worst Match
Chelsea and the redhead
4 of 7
Are You There, Chelsea?
Chelsea's Worst Match
Chelsea and her gay gynecologist
5 of 7
Chelsea
Chelsea's Worst Match
Chelsea and the French chef
6 of 7
Chelsea
Chelsea's Worst Match
Chelsea and the emotional marketing executive
7 of 7
Are You There, Chelsea?
Chelsea's Worst Match
Chelsea and the minor (turned major) league baseball player