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What is this?
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Here, Em furthers the airspace luggage / love life metaphor (see jet plane, fly and airhead above). In a relationship, baggage is your past bad experience. Heart as damaged goods also refers to an upset emotional state. Case and overhead space fits the luggage side of the metaphor and a headcase is a mentally unstable person. He basically says you shouldn’t love him (put your heart in him) because you are an emotional wreck and he is nuts.
Slick wordplay. Perhaps a heart belongs in a heart case. A head belongs in a head case. But when a u put your love into someone who’s mental it is not gonna be a good decision.