Awkward, but is it grammatically correct? “It was Jen's and my first date.” Logic: It was Jen's first date. It was my first date. She and Jen hate each other. (Correct?) Thanks.
According to the Chicago Manual of Style, when two nouns possess the same entity, only the second takes the apostrophe: Jen and my first date. You're right. It is awkward because of the personal pronoun ("Jen and Mike's first date" would flow much more smoothly). So, I wouldn't use it. I would say "Jen and I went on our first date". "She and Jen hate each other" is correct.
