User blog comment:B214/Shin DxD 1 discussion/@comment-2607:FB90:3851:A5D3:0:14:ECCB:7501-20181029115052/@comment-108.7.145.117-20181030014524

"Sure, he's fighting his friends but again, it's not a death match. If they get defeated then they simply retire." They retire because they are heavily injured.

"Rias is a princess but why should that matter? She's no stranger to combat." 1) Still not a warrior 2) She is a glass cannon, her ability to withstand attacks is low compared to Issei, and neither her offense nor defense hold a candle to his sheer strength. He could kill her easily with a miscalculated blow, The retiring mechanism is not instant. 3) Rias is extremely prideful and she will not be holding back, but if Issei replies in kind... see number 2.

"Also Rias would feel insulted if Issei went easy on her." That's not what I said, what I said is that he would be conflicted for a variety of reasons He can beat her and win the match but risk hurting his friends and lovers and also possibly knock Rias out of the Finals or lose the match and prevent this, but fall out himself. Who and what will he priorotize.

"Rias and Issei are both competitive and hate to lose." And yet Issei is far more self-sacrificing

"If anything he would just use one of his perverted techniques such as Dreak Break." It's my turn to tell you that you likely pay not attention to fights, he probably wouldn't use it on Rias because he doesn't want to embarass her by publically denuding her.

"The issue with Ravel was her trait of "Supremency" which clased with Issei's trait of "Rightenous". Ravel's mother brought this up in volume 24. But that issue was already solved." When was it solved, Volume 25 had the battle plan worked upon by Ravel. Issei is still growing in that regard, and he is far behind Rias's abilities in that area, he lacks the ruthlessness needed to take down Rias bodily - because he cares deeply for her and is not accustomed to fighting her. The only time this has happened before was the non-canon Anime fight after she was infected by the Juggernaut Drive/Loki's curse.

"Issei has come a long way and has learned to keep his emotions in check during rating games." Correction, he has learned to keep his anger in check, the issue here is not anger, but the opposite of anger.

"she had no problem showing Strada her resolve to fight Issei." Strada is part of her challenge to Issei, to overcome the wall that is his emotions to her, for him to take his own goals as priority, even if it means beating her.

"you think Rias was worried about Strada?" Strada easily wore down Arthur Pendragon, the most skillful and powerful sword user in the series so far. He easily knocked back the Le Fay Pendragon's giant mecha Gogmagog (10 meters tall) and he would cut through swathes of buildings like fucking Zoro from One Piece with a single sword swing, and so precisely that the buildings did not collapse. He fought and beat Kokabiel, a leader class Fallen Angel who was on par with the Mao and Arch-angels of heaven in power, who themselves were near god level. Strada's holy aura is an additional problem for Issei THE DEVIL-DRAGON. Strada is also among those who fought against Trihexa and came away uninjured, which is no mean feat considering that it eliminated high and ultimate class devils with ease and could crush Gods. Strada is not the only challenge either, Crom Cruach is physically stronger than Ddraig even if Ddraig has more special abilities, and Kiba has never been hit by Issei in their sparring matches, EVER, even when Issei went all out, and can make Dragon-slayer holy and holy demonic swords (so double the damage), not to mention his possession of Gram and the other Demon Swords that once belonged to Siegfried. Then there is Akeno, who may lack Barakiel's physical strength but has her lightning dragons and impressive magic ability as well as her Queen piece. Koneko is also powerful enough to easily one-shot Evil Dragons up to the Grendel-clone level (the same Grendel dragon that in the Qlippoth arc, took the combined forces of Rias' whole Peerage to destroy (and even then incompletely). Rias's team are easily on par with Issei's in terms of strength and thus that makes this a game of skill and determined, timely strategy... something that can be handicapped if blinded by emotional attachment to the opponent(s)