We were sitting on his couch, talking about our derailing romance, hashing out whether we’d be able to remain friends. And then the subject changed to his career aspirations. As he spoke so animatedly about what he wanted to do, a light went off in my head: I could never be with someone whose job I didn’t really give a s*** about. That’s when I said abruptly: “Oh my gosh, we can totally be friends!” He looked confused.

—Jenna

Aftermath: A few weeks later, I met a fascinating urban planner.

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