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In this song, the character is is over 40 and she has a great job but all her life she hasn't met that guy or partner that she dreams of having. She tries the bar to just simply enjoy a drink after a long day, but somewhere in her mind, she's looking for that guy unconsciously. She looks around just looking at people. She sees a man alone... and thinks "would he say yes if I ask him out" but thats just in her mind thinking. Soon after, a girl comes next to him and realizes that he was waiting for her to meet. And then in her mind, another question " so who's that girl?". A woman can have long conversations in her mind and imagine things alone. She`s not insecure, but she's kinda lonely sometimes. "Damedesuka?= why NOT me?"