While a guest on Late Night with Seth Meyers (2014), Andrew Rannells said that because he was the only gay man on the set during his sex scene with Corey Stoll, Rannells was asked to choreograph the scene. As he and Stoll had not known each other for very long, he felt the need to come up with small talk between takes while they were lying together naked. Rannells said that in an effort to make the shoot less awkward, he would ask Stoll questions like: "So what are you going to name your baby?" and "What's your wife wearing to your wedding?" while in the most intimate positions.
The title of this episode comes from the (real) tumblr that Marnie and Hannah discuss, "Old Loves," which publishes photos of celebrity couples who are no longer together. In 2014, Lena Dunham told Entertainment Weekly magazine that she was once scrolling through Old Loves when she discovered a photograph of her own (then-)boyfriend, musician Jack Antonoff, with his high school girlfriend, actress Scarlett Johansson.