Jennifer Lopez and Ben Affleck Engaged: How They Made Their Relationship Work This Time Around

The 'Marry Me' star announced on Friday that Affleck popped the question.

Jennifer Lopez and Ben Affleck are living proof of the old adage the heart wants what it wants. And now, some 20 years after they first got engaged, the singer and actor are giving marriage another go, but with added perspective.

Bennifer -- as they were aptly dubbed back in the day -- first got engaged in November 2002 but broke things off in January 2004. Following their split, they each embarked on new lives with other mega stars. Lopez married Marc Anthony in 2004 and welcomed twins Max and Emme in 2008. She and Anthony split in 2014. Affleck would marry Jennifer Garner in June 2005 and had three children -- Violet, Seraphina and Samuel -- before separating in 2015. Their divorce was finalized in 2018.

Ben and J.Lo rekindled their romance in February 2021, after she and Alex Rodriguez called off their two-year engagement and called it quits after four years of dating. A source told ET back in May 2021 that it was the Armageddon star who began pursuing her again after they remained on friendly terms following their 2004 split. That source added Ben "always had an affinity for Jennifer and was the one who initially started pursuing her and making an effort to reconnect, romantically speaking."

They've done exactly that, and they've been inseparable ever since. Now, with a second engagement in the books, one's left to wonder how the couple plans to do things differently this time around. For starters, it starts with not putting so much pressure on the relationship.

Months after their reconciliation, a source told ET that ever since J.Lo and Ben reconnected, "what's made their relationship work is not putting pressure on it and just living in the moment and enjoying each other's company." In the end, Ben and Jen "just want to be genuinely happy together in life."

That same source told ET that Ben and J.Lo having separate life experiences really helped them grow individually.

"They have both conquered new life experiences, have had other relationships, and have grown tremendously since they initially got together years ago," the source told ET. "They have both recognized that and it's been really healthy for them."

Prior to Lopez announcing the engagement, the couple purchased a $50 million mansion in Bel Air. A source told ET last month that the big purchase was the next natural step for them.

"Ben and Jen want a house together in L.A., and probably a couple of other places as well, but this house in Bel Air is so great for them. They spend every night together when they can, and having this home will make that easier. It’s the next step in their relationship and since they are both in it for the long run, they can't wait to have a home together," the source shard.

At that point, the source said Ben and Jen were "excited" to further solidify their relationship and take that next step, as a couple and as a family unit as they hope to "bring everyone together" and have their families grow even closer.

"Jen and Ben are excited to further solidify their relationship and take this next step. At this point, they know they are meant to be together and they are prepared to elevate their relationship in this way and include their families in the process and bring everyone together as a healthy unit," the source explained. "It will be great for the kids and everyone is excited and can't wait to get even closer."

Just last month, a source told ET that getting engaged was an "ongoing conversation" for the couple, and it helped that they were open and honest about their previous engagement. The same source told ET that they actively talked about what didn't work in the past while using those experiences to strengthen their relationship now, culminating with Ben popping the question and Jen responding with a resounding yes.