Madison Beer and Justin Herbert engagement (Getty Images)Justin Herbert and Madison Beer just got engaged, and the internet is already obsessed. The Chargers quarterback got down on one knee "in front of a romantic landscape," and Beer said yes, sharing the news with a simple Instagram caption: "meet my fiancé." But before the two found their way to each other, both had their own dating chapters. Some sweet, some messy, one involving a Vine star and a very public fallout. Here's a look back at who they dated before saying "I do" to forever.Before Justin Herbert, Madison Beer dated a Vine star, a Beckham, and a Hype House memberBeer's love life has played out largely in public since her teens. Her first serious relationship was with Vine star Jack Gilinsky, whom she started dating in 2015 at just 15 years old. The relationship ended in 2017 after a leaked audio recording appeared to show Gilinsky being verbally abusive toward her. Beer later said she stayed in the relationship trying to "fix him," and warned fans not to make the same mistake. She followed that with a low-key summer fling with Brooklyn Beckham in 2017, which fizzled once he left for college in New York, then an on-again-off-again run with DJ Zack Bia from 2018 to 2019 that's widely believed to have inspired her hit "Selfish." She was also frequently linked to YouTuber David Dobrik, though neither ever confirmed it. Her longest relationship before Herbert was with Hype House's Nick Austin, which lasted roughly three years before split rumors surfaced in December 2023. Fittingly, when the Herbert rumors first broke in August 2025, Austin reacted to the news of his ex moving on by posting a Pink Panther meme, a petty little parting shot that fans haven't forgotten.Justin Herbert's dating life was quite a mystery before Madison Beer Herbert, on the other hand, has kept his love life almost entirely under wraps. The only name that's consistently come up is NFL reporter Taylor Bisciotti, who he was rumored to be linked to before Beer entered the picture, though neither side ever confirmed anything. True to form, the quarterback has said before that he'd rather people know as little about him as possible, calling himself someone who doesn't even want to read an article about his own life. That makes this engagement one of the few times fans have gotten a real window into his personal world.The happily ever after had their own ups and downsWhat's notable is how different their dating histories look on paper. Beer's relationships have unfolded almost entirely in the public eye, often soundtracked by her own music. Herbert's have stayed private enough that most of what's "known" is speculation. That contrast followed them right into this relationship. Beer revealed on a podcast that their actual first date happened at her house because they were both too nervous to be seen in public, admitting their conversations run so deep she "could have her hair on fire" and not notice.Their romance wasn't without its critics, either. Herbert caught heat earlier this year for skipping voluntary team workouts to join Beer on tour, with commentator Skip Bayless accusing her of pulling focus from his football career. Chargers coach Jim Harbaugh shut that down fast, praising Herbert's work ethic and saying he was "happy" his quarterback had "good balance" between football and his relationship.Now that the two are engaged, it's a case of two very different approaches to fame and romance landing in the same place, one who's dated in the spotlight her whole life, and one who's spent his career avoiding it. Fans are already calling it one of the more unlikely power-couple pairings of the year, and with a wedding presumably on the horizon, don't expect either of their dating histories to stay quiet for long.