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"So if I hadn't had to repeat the year, would you have gone out with me?" "I don't like hypothetical what-if talk."

Literal

"Then, repeat-year-do-not-[conditional-たら] go-out-give-[explanatory-question-んの]?" "Tarareba-talk [topic-って] like-not [explanatory-の]"

Excellent slang example. タラレバ話 ('tarareba talk') is a Japanese-specific term for 'hypothetical regret talk' — combining the two conditional endings ~たら and ~れば, which are the grammar forms used to construct 'what-if' statements. A noun derived from grammar forms, similar to English 'coulda-shoulda-woulda.' 留年 ('repeating a year') is a specific university/school term. んの is the ultra-casual contraction of のだ.