When Joe Biden proposed to Jill Biden, it wasn’t actually a one-time deal. In a surprising and arguably odd twist, he had to ask for her hand in marriage a whopping five times before she said “yes.” Talk about persistence. To be fair to Jill, she had some pretty understandable reasons to hesitate on getting hitched, including a failed first marriage, a budding career, and plans for graduate school. “I knew that if I married Joe, I’d have to give up my apartment, the only space that was just for me,” she wrote in Where the Light Enters (via Time). “I’d have to quit my job for the boys’ sake … And I’d have to become Jill Biden, senator’s wife. It was all too much.”
After her initial rejection, Joe popped the question three more times, before giving Jill a stern ultimatum in 1977. “‘I’ve been as patient as I know how to be, but this has got my Irish up. Either you decide to marry me, or that’s it — I’m out. I’m not asking again,'” she went on to recall him saying in her memoir. “His blue eyes, normally alight, seemed clouded with gray. ‘I’m too much in love with you to just be friends.'” Of course, she eventually agreed to his proposal, and the rest is history. Although this story ended on a happy note, an ultimatum isn’t most romantic of gestures.