The Bachelor stars were all smiles as they posed for cameras ahead of the star-studded event at The Rooftop at Pier 17 at the Seaport in New York City.
The pair spoke with ET on the carpet and opened up about making their red carpet debut together, after giving their romance a second shot earlier this year.
"This is probably one of the fancier date nights we've had," Kirkconnell explained. "Usually it's a low-key spot getting pasta or pizza around the city, so I think this is one of the more fancier ones."
James, 29, looked stylish in a brown and black plaid suit paired with black loafers and amber aviator shades. Meanwhile, Kirkconnell rocked a black dress with a plunging neckline and semi-sheer sleeves and skirt.
James also reflected on why they decided to enjoy a date night at the ESPYs, explaining, "I live vicariously through some of my friends who are playing professionally."
"What a good weekend for sports," James added. "I couldn't think of a better place to be celebrating tonight."
"I am probably the most unathletic person, so I'm very excited to be around such talented people tonight," Kirkconnell added with a laugh.
On the finale of his season of The Bachelor, James fell for Kirkconnell, but by the time After the Final Rose aired, the two had called it quits amid Kirkconnell's high-profile scandal in which she was accused of racist actions in the past. Kickconnell subsequently apologized publicly multiple times.
"She was like, 'If you're going to make this work, let's do it. But, if you’re not going to make it work, I’m going to let you do your own thing,'" James recalled during the latest episode of the Pomp podcast. "That’s really all I needed. It was an ultimatum that I needed. It’s been great."
"It was honestly a commitment that we made to each other that we were going to work on the relationship," he continued. "There came a point in time where it was evident that my working on the relationship looked different than Rachael’s because I wasn’t really honoring that commitment that I made to working on the relationship."