Vanessa is disgustingly gooey and romantic so she probably adores his powers and hope he uses them for good, haha.
He can definitely flirt with Nessie - I think their pbs were on a show together! - but alas, her heart not-so-secretly belongs to ~chaosbomb.
I also have tothegunshow. I would be very amused to see Cupid using his powers against Dean until he learns to push past them because a) he's hyper masculine and SUPER DUPER HETEROSEXUAL, OKAY~ but also because everyone else who hits on him gets griped at, haha. :]