"With Pen In Hand" is a song by Bobby Goldsboro that tells the story of a breakup and the aftermath of a relationship ending. The lyrics depict a person who is about to leave their partner, symbolized by signing their name on a document, possibly a divorce or separation agreement. The song expresses the loneliness and heartbreak that both parties will experience after the separation. The singer acknowledges that the love they once had may be difficult to regain but believes they can make it up to their partner. However, if their partner thinks it is impossible to rekindle their love, then the singer will accept the situation and leave, leaving their partner to fend for themselves. The song also touches on the concern for their child, Jenny. The singer questions if their partner will be able to take care of Jenny, support her emotionally, and raise her well in their absence. If the partner can fulfill these responsibilities, then maybe Jenny won't miss the singer as much. In the last verse, the singer imagines the partner lying in bed, feeling the absence of their presence. But, they wonder if their partner will have no desire to kiss or hold them anymore. The singer then ponders if their shared good times outweighed the bad times, and encourages their partner to go ahead and sign the necessary papers, signaling their departure. Overall, "With Pen In Hand" portrays the emotional struggle of a breakup, the concern for a child's well-being, and the acceptance of moving on after a failed relationship.
