Ben Affleck Used The Same Tactic To Romance Both Jennifer Lopez And Jennifer Garner

They say a leopard never changes its spots, and when it comes to Ben Affleck, they might just be right. Once wedded to fellow actor Jennifer Garner, the "Justice League" star has since remarried, and later divorced, singer Jennifer Lopez following a turbulent on-again, off-again relationship that stretched across decades. While Affleck might have trouble keeping his leading ladies, he certainly knows how to impress them, at least in the beginning, and it's notably with one tried-and-tested method. Although it probably sounds a bit retro to Gen Zers, the Oscar winner's preferred love language is, in fact, email.

Affleck originally met Garner on the set of "Pearl Harbor" all the way back in 2000. At the time, Garner was married to fellow actor Scott Foley, with Affleck proposing to J.Lo just two years later. Fast forward to 2004, however, and Garner was divorced, while Affleck had also split from his famous fiancée, leaving both of them single. The celebrity couple was first spotted out on a date at a Boston Red Sox game and, by 2005, they had tied the knot in an intimate Caribbean ceremony.

In a 2010 interview with Parade, Garner looked back on how it all began. The "13 Going on 30" lead acknowledged that of course the timing was right since they were both unattached, sweetly adding, "He's a very good writer. [...] He's a very persuasive writer" in relation to Affleck's emails, which were seemingly his version of love letters. When pressed on whether she still had them, Garner confessed to saving them all. Sadly, the couple called it quits in 2015, but with Affleck single again, he was free to try out his signature move once more.

In the meantime, Jennifer Lopez had her own relationship dramas to deal with. After a clandestine wedding to musician Marc Anthony in 2004, after which they welcomed twins, the pair sadly parted ways in 2014. Brief romances with Casper Smart and Drake followed, before she settled down with baseball legend Alex Rodriguez. The celebrity couple had plans to marry, but they ultimately split up in 2021 — ironically, when J.Lo was filming "Shotgun Wedding" alongside D'Arcy Carden. The timeline was muddied somewhat when TMZ reported that Ben Affleck and his former flame had been emailing each other as early as February of that year. 

The "Argo" director was doing exactly what he had done years prior with Jennifer Garner: Charming his way into her inbox. If it's not broken, don't fix it, right? Even more tantalizingly, according to insider sources, they weren't friendly catch-ups either but more emotional missives reminiscing about the good old days. The whole world learned about the emails, and the hilarious nickname "Pen Affleck," in 2024 documentary "The Greatest Love Story Never Told." The "Love Don't Cost a Thing" hitmaker even detailed how they inspired some of the songwriting on her album, "This Is Me... Now." 

Affleck reportedly complimented Lopez on how pretty she looked in recent paparazzi shots and even expressed a desire to visit her on set. Apparently, the two kept in regular touch until the shoot finished in April, coincidentally around the same time her split with Rodriguez was announced. From there, a whirlwind romance blossomed. The reunited couple married in Las Vegas in 2022 and had a second ceremony in Georgia two months later. But, by 2024, Bennifer separation rumors had started to swirl, and J.Lo eventually filed for divorce. If only all relationships could be as easy as hitting "send" on an email.