Examine their past romances, from traveling the world with Leonardo DiCaprio to getting engaged to Alanis Morissette.

01

LEONARDO DICAPRIO: 2011

Combining work and play? An N.Y.C. dinner to discuss an upcoming project turns into a world-tourist romance in May 2011 when Lively and DiCaprio sail the French Riviera, tour Italy, and bike the streets of New York City before calling it quits in October 2011 for “amicable” reasons. Their relationship started in November 2010.

02

RYAN GOSLING: 2010

After a sweet October 2010 Disneyland date, Gosling and Lively are seen getting flirty at a December N.Y.C. afterparty for his tearjerker Blue Valentine. They are only briefly linked before Gosling tells PEOPLE, “She’s an incredible actress. She’s a good friend. You’re not allowed to have friends in this business.”

03

PENN BADGLEY: 2008 – 2010

Observed: The resident couple of Gossip Girl enjoying their romance off-screen in 2008. Following Badgley’s exclamation to PEOPLE that his costar is “an amazing person and she’s beautiful,” a romantic holiday to Mexico culminates in a snapshot of the two sharing a kiss in a pool. They did, however, break ways in October 2010, one month after Lively told Allure, “I don’t comment on my relationships.” Just like their on-screen counterparts.

04

SCARLETT JOHANSSON: 2007-2010

In April 2007, Hanson is spotted holding hands with Reynolds in New York City, not long after assuring Seventeen magazine that she is unmarried and not searching for love. A year later, the pair gets engaged, and that September, they tie the ceremony in sєcrєt. But in a joint statement released in December 2010, they add, “After long and careful consideration on both our parts, we’ve decided to end our marriage.” “We entered out relationship with love, and it’s with love and kindness we leave it.”

05

ALANIS MORISSETTE: 2002-2007

In 2002, at Drew Barrymore’s birthday celebration, Morissette discovers a unique admirer in Reynolds. The singer tells PEOPLE, “We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate,” just prior to Reynolds proposing in June 2004. Following years of intermittent relationships, the two finally call it quits in February 2007, which is two months before he starts dating Johansson.

06

RACHAEL LEIGH COOK: EARLY 2000s

Prior to her 2004 marriage to actor Daniel Gillies, Cook spent the early 2000s courting Reynolds. She admitted to dating in the past to InStyle in 2005. “It was one day after our wedding that I noticed my ring in the mirror and thought, ‘Wow, the celebration is over.’” But since I was never very good at it, I’m really happy.”