The Selling Sunset Star Ben Affleck Supposedly Tried To Date Before Getting Back With J-Lo

Ben Affleck was super single –- and trying to mingle — before getting back together with Jennifer Lopez in May 2021. The superstar a couple first got together in 2002, spawning the iconic Bennifer ship name. Affleck proposed to the "Jenny From the Block" singer with a six-carat pink diamond, according to Us Weekly, but the high-profile pair ended their engagement in 2004.

Lopez married singer Marc Anthony that same year and had twins, Emme and Max, with him. Lopez and Anthony divorced in 2014. Lopez went on to another high-profile romance and engagement with former MLB star Alex Rodriguez. The two split in 2021 amid rumors Rodriguez cheated with "Southern Charm" star Madison LeCroy. In an interview with Page Six, the South Carolina-based reality star vehemently denied ever having a physical relationship with A-Rod. Meanwhile, Affleck married actor Jennifer Garner in 2005 and they had kids Violet, Seraphina, and Samuel before divorcing in 2018, per InTouch.

There was no scenario in which any Bennifer shippers ever thought their ships would cross paths again, but 2021 found them single at the same time. After rekindling their romance, the lovebirds announced their engagement in April, per People, marking a mere 18-year detour to their potential walk down the aisle.

While the unexpected rekindling of Bennifer has fans ecstatic, Ben Affleck was active on dating apps before finding his way back to Jennifer Lopez. And the romantic reboot may not have ever happened if a Netflix reality star had accepted Affleck's advances. 

On a Season 5 episode of "Selling Sunset," 30-year-old luxury realtor Emma Hernan claimed that the 49-year-old actor reached out to her after they matched up on the dating app Raya — before he got back with J-Lo. "He may or may not have been texting me," Hernan told co-star Chrishell Stause of Affleck in the episode (via Us Weekly). "He may or may not have asked to grab ... coffee a few times." Hernan claimed that Affleck's "opening pickup line" to her referenced the fact that they both hailed from Massachusetts, but she found his approach more heartwarming than creepy. "We have the Boston connection," Hernan said. "It was very sweet."

While Affleck sent Hernan some DMs, she never met up with him in person. But Stause was tickled pink by the possibilities. "You could've foiled Bennifer," Stause cracked, noting that the Oscar winning star was "on the hunt." Hernan elaborated on the situation on the "Today" show, telling the morning show that she did talk to Affleck, but nothing more came of it. "We talked for a little bit," she said. "We never met up. I think this was pre his relationship ... before his current one now. He was super, super sweet."