I think it's an interesting idea, but I'd be more willing to throw money away if it were going for charity rather than just to fill LJ's coffers.
Meaning, I'd Really Like to have Paul give Lilith and Aerden give Z'leena the bouquets of a dozen roses, but I'm too cheap to spend $6 on pixels whose image will disappear in two weeks. I'd rather just send Viv and Anna real roses.
However, you have all been warned: Tomorrow, I will be giving Valentine's Day gifts from my characters to characters they love.