「お父さんとうまくいってないのか」「・・・」「すまない。立ち入ったことだった」

「」「・・・」「。」

'Things not going well with your dad?' '...' 'Sorry. That was too personal.'

Literal

'Father [with-と] well going-not [question-のか]' '...' 'Sorry. Intruding thing was.'

うまくいっていない 'not going well' contracts to うまくいってない. 立ち入ったことだった 'it was an intrusive matter' — 立ち入る means 'to enter, to pry,' and the past tense acknowledges crossing a boundary. The silent 「・・・」 is a powerful narrative device showing discomfort. すまない is a masculine apology, more earnest than ごめん.