These college sweethearts celebrated their engagement with a summer portrait session at the Art Institute of Chicago

Bennett (he/him) and Danny (he/him) met during college a few months into a Spanish course. They joke that they could have met even earlier if Bennett hadn’t ignored the guy who sat next to him on the first day, but they eventually started chatting, and Bennett began to tutor Danny. After two years together, the pair decided to split when Bennett moved to Madison, Wisconsin, to get his master’s degree.

A few years later, Danny found himself in Madison on a Sunday night in the fall. On a whim, he reached out to Bennett to see if he still lived in Madison and wanted to get dinner. One thing led to another, and they began dating once again. Soon after they got back together, Bennett had the opportunity to spend two weeks in Switzerland for work. He invited Danny along, and they added a week in Italy afterward. They spent three weeks in close quarters hopping between hotel rooms and small apartments, joking about how they’d probably end up getting married one day.

After several months living together, moving to a new state and adopting their adorable shih tzu, Leo, the boyfriends knew it was finally time for someone to propose. Even though the plan was always for Danny to be the one to do it, Bennett decided to take the initiative and surprise his partner. Using his birthday weekend as cover to get dressed up, Danny picked up dinner from one of their favorite restaurants, and they had an elegant dinner at home. When they were done, Bennett asked Danny if he wanted to get married one day, to which Danny replied, “Of course.” Then, Bennett got down on one knee, pulled out a simple brushed gold engagement ring with a single diamond inset and asked, “Do you promise?”

Not long after, Danny found a time for his own proposal when the couple was on vacation in Northern Wisconsin. On the first night there, after a home-cooked dinner with a bottle of wine from their first trip to Italy, Danny got down on one knee and proposed with a custom engagement ring made of family diamonds and three shades of blue gemstones, a design he chose because it was “fancy and special, just like its wearer.”

To celebrate their engagement, the two husbands-to-be spent a weekend away and had engagement pictures taken at the Art Institute of Chicago. The engagement photographer led them through the museum’s galleries, atrium and outdoor garden space. Danny and Bennett wore casual outfits for the photoshoot, donning shorts for the outside pictures and putting on matching white button-down shirts and complementary wristwatches while inside. As they wandered around the museum, the college sweethearts mused about how excited they were to finally call each other husbands.