The day after their first date in February 2021, Damian Courtney Dizárd surprised Conswella Gilmore with a silver ring from David Yurman.
“Like the younger generation says, I wanted to shoot my shot,” Mr. Dizárd, 51, said. He then invited her to Miami for his birthday trip the month after, and Ms. Gilmore, 50, agreed to go.
They had been talking on the phone at all hours of the day for four months. “We built up a friendship, and then I felt comfortable enough” to make a move, said Mr. Dizárd, who goes by Chip.
They first met on Instagram in November 2020, when Mr. Dizárd went on Instagram Live and spoke about the importance of dreaming big. Ms. Gilmore had been following Mr. Dizárd, a wedding and event photographer, and his words resonated with her. She messaged him and they talked on the app for weeks. Then they moved their conversation over to phone. “We were talking about everything,” she said.
They had their first date at Woodmont Grill in Bethesda, Md., where he asked questions about her impression of him, such as “How did you feel when you first saw me?” He playfully took her phone and recorded her responses. (These days, they look at those photos and videos and reminisce on the good times from that night.)
The next day, they met at the David Yurman store in Washington and decided to browse around. Ms. Gilmore had her eye on a silver ring, but then her mother called and she stepped out of the store to pick up the phone. When she walked back in, Mr. Dizárd said, “I bought you the ring.”