Stick to the bro code, Kris is interested in Jessica but he was too shy to do anything about it so Chanyeol decided as bros to be his wingman and without Chanyeol, Kris wouldn't have managed to be with Jessica. according to the bro code, a bro who completed his mission deserves a girl as a way to pay your respect to him, Kris is terrible in being a wingman so he decided for easy route which in reality is the hardest route in existence. 

The only reason Chanyeol was successful in making Jessica with Kris was that Jessica had a deal with Chanyeol, Chanyeol said that he'll be finding a guy for Jessica, what are the chances, he found a guy who likes a girl and girl who wants to be like who happens to be the girl that the guy likes. In keeping with her promise, Jessica is suppose to find a girl for Chanyeol, unlike Kris who went with the short route, Jessica puts a lot of work in finding a girl suited for Chanyeol and the girl seem to like Chanyeol on the surface. 

Originally Chanyeol knew that only one of the either two 'clients' can find a girl for him, as back up if one fails he made a deal with both but it turned out the two were 'successful' in finding a girl for Chanyeol the only problem, unlike the miraculous Kris and Jessica situation where one guy is interested in a girl and a girl is interested to be with a guy, the two found two separate girls, one girl is interested in a guy and one girl is interested to be with a guy, the question now is 'who is who' 

Of course Chanyeol must put an effort also who will he pick to be with him, truthfully he shouldn't be worried who will he pick to be with him but who will pick him.