Edit:(forgot the disclaimer) Disclaimer: I don't own Naruto and never will.
Was that too forward? Sneaking a glance at the object of the desire they came to the conclusion, definitely a terrible choice of words, especially since it seemed the object of his affections clearly didn't know who they were. Our brave protagonist opened their mouth to apologise and try to fix this situation-
"Would you like to restart this conversation? I feel like that would work out a lot better for you in the end."
A beacon of light split through the darkness they had been sure would consume this entire situation.
"That- that would be welcome." clearing their throat. Then paused seeing 3 familiar faces disappear behind a newspaper, from here the protagonist could see their shoulders shaking and could easily imagine their faces filled with mirth. Those three were going to die painfully. Sighing they continued, putting that aside.
"I like you, please go on a date with me, I know you probably don't know anything about me but please, just one date before you decide anything."
"...You know I must say that really wasn't an improvement from your first try."
"Um..."
"Look, Mr. Protagonist, if you're looking for someone, play a joke on or screw over please choose someone else, I have more pressing matter to attend to." Like whether or not Basil will live to see another chapter.
"No, it's not like that. I really do like you, and I'd really like you to go on a date with me."
"Hypothetically speaking, if you for some reason actually did, that is a terrible idea, why would you go do something like that."
Without hesitation the reply came, earnest as ever.
"I like you, whether you believe it or not my feelings won't change."
"Then you'll excuse me for not believing you."
"What do I have to do to convince you I'm being sincere!"
"If you are being sincere I think you should go see a psychologist about this delusion of yours."
"And if I'm declared sane?"
"Well, clearly someone needs to burn his degree."
"Then what would actually convince you I'm sincere."
"...logically speaking nothing. You should give up and find someone else."