(Source: Axelle/Bauer-Griffin)
Prev 19 of 19 Next
19. Sara Gilbert and Linda Perry
Linda Perry orchestrated an epic proposal for her actress girlfriend that involved a surprise performance by a string band, during which the singer took out five different T-shirts, reading "Will you marry me?" word by word. 

After that, the ladies' moms and friends appeared, along with singer Tom Waits. He serenaded the gals with their song, "Missing You." Gilbert said in a later interview: "We had our proposal with our breakup song, which is great."