First of all, how did they even know Medea's name? Did he even introduce her to Grayfia when she visited?
Secondly, wtf is this. Who makes a bet like that regardless of how weak/strong the opponent is.
Either you win and you look like a smug/arrogant bastard or you lose and look like a loser. Literally phyrric victory here.
I hope his shop points are worthless. He's never used it. I can already imagine his current mission reward not even equating to a thousandth of the price of a desirable shop item
Do not want harem in DxD? Hahahahahahahaha Hypocrites. Author-dono, please forgive us. I recommend you have your harem lists closed. It is not for nothing but human beings we are subconsciously influenced and there are hundreds of possible waifus Hahahahahaha. You do not like Rias ??? It is what there is, it is so in addition to that has already been hinted that it will not be the same.
KENSIST