Today, I guess nobody would use "Hallo mein Lieber" to initiate a serious flirtflirtatious with somebody (using "du" in this sentence sounds wrong to my ears). This sentence has (if said to an adult) an ironic undertone, in which case you could say that someone initiated flirtatious while joking about it if this makes any sense.
Same goes for "Hallo mein Süßer / meine Süße".