気になる人をデートに誘おうといろいろ考えてきたものの、みごと撃沈。
「話の着地点を見失う」はあるあるだと信じたい

この子ですね　→　post #1959094

Thinking about inviting the person she has a crush on, she splendidly failed.
I'd like to believe that the "lost sight of the point of the conversation" happens a lot.

She's this girl　→　post #1959094