Danny and Anna grew up having dinner with each other's families every year at the NAFWB conventions or the Pinsons' trips to Miami. Neither, however, would have ever thought anything about the possibility of a future together.

The two crossed paths at Welch College as students together for one year but didn't connect until the wedding of Danny's brother Samuel and Anna's best friend Elizabeth in the summer of 2023. Since Danny and Anna were the best man and the maid of honor, they had several opportunities to talk. Danny would later reveal that the wedding was when he first saw a serious future with Anna.

When the school year at Welch began that fall, Danny found opportunities at events to talk to Anna. At one party, they found themselves talking for nearly the entire time. By the end, Danny asked Anna to stop by the college coffee shop where he worked. When Anna visited him during his shift, they talked for two hours, and he invited her back again, then again, then again. During this time, Danny and Anna realized they got along awful well, and they went out together more and more often.

They made it official on October 7, 2023, after enjoying a jazz concert together. They spent two years together enjoying conversations, theater, music, day trips, and long walks before Danny proposed on April 24, 2025.