Penny Benjamin (Jennifer Connelly) is Maverick's old flame, who reappeared when he returned to Top Gun. Penny and Maverick became estranged over the years after he took her on a date aboard a stolen fighter plane and Mitchell was nearly discharged from the Navy. Penny appears to understand Maverick in a way that no one else does, and their mutual attraction is evident, but she wasn't sure she could commit to him, and vice versa, given Pete's track record for being unreliable. However, Penny realized that Maverick had grown up and that he still wanted to give something back to Top Gun because his career as a jet pilot was far from over.

Penny was gone when the jubilant Maverick returned to Penny's bar, The Hard Deck, following the film's climax mission because she had gone on vacation with her teenage daughter, Amelia (Lyliana Wray). Penny probably fled because she was afraid Maverick wouldn't return from this assignment, even if it wasn't stated explicitly. Penny returned and reconnected with Maverick after word reached her that he was in love and had returned home. Charlie (Kelly McGillis) was Maverick's lone previous love interest in Top Gun, but that was 35 years ago. Maverick and Penny appear to be more evenly matched, and she may be the one to persuade Pete Mitchell to commit to a long-term relationship.

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