When Jennifer Lopez’s Ex Alex Rodriguez Hung Out with Ben Affleck’s Past Love Interest

In a move that once ignited the Hollywood rumor mill, Alex Rodriguez, the ex-fiancé of Jennifer Lopez, was spotted hanging out with Ben Affleck’s ex-girlfriend, Lindsay Shookus. In 2021, the two were seen together at Shookus’ birthday party in the Hamptons, igniting a wave of intrigue as at the time Lopez and Affleck had rekindled their old romance. Fast forward to 2024, Affleck and Lopez separated just two years after tying the knot.

As per The Sun, the sighting happened at an intimate gathering where magician Josh Beckerman performed for birthday girl Shookus, Rodriguez, and his business partner, Marc Lore. Footage from the event was shared on social media, immediately capturing attention. An insider said, “It’s certainly going to raise eyebrows, given Ben and Jennifer are back together so publicly. What are the chances that both of their exes have now hooked up?”

However, Rodriguez’s rep denied the allegations. “There is absolutely zero there. They have been friends for 15 years.” Rodriguez’s appearance with Shookus came just months after his high-profile split from Lopez. According to sources, “It definitely hurt his ego. [Rodriguez] was under the impression that he and Jennifer would go on as friends, but he is acting so needy that Jennifer cut him off. Jennifer seems very happy. She tried for a long time to get her relationship with Alex to work. She feels good that she decided to break it off. She just doesn’t trust him and didn’t want to waste any more time.”

Despite the public’s fascination, Rodrigues was focused on moving forward. Back then, in an Instagram post, he hinted, "I am about to step into a new beginning in my life. Anything that doesn't serve me is clearing out of my life. New energy is emerging. New levels are unlocking for me mentally, physically, and spiritually. I am remaining patient and know that this new phase of my life is coming," as reported by People magazine. 

At the time, Lopez and Affleck were head over heels for each other. Sources claimed, “She wants to give it a shot with Ben. They never really had closure and she has always wondered what could have been. The timing was never right and they were in different places until now.” Another source added, “Jennifer is still very excited about how things are going with Ben.”

Meanwhile, Shookus, the Saturday Night Live producer, dated Affleck on and off between 2017 and 2019, during which time their relationship also drew major media attention. Insiders revealed to Us Weekly, “She has a kid and an ex-husband and a job in New York and Ben has his family and a job in L.A., and while they love and respect each other, they just realized it wasn’t going to work.”