Who was the first openly gay Sexiest Man Alive?
Jonathan Bailey (2025)
"What, like it's hard?"
Legally Blonde (2001)
Which couple both famously wore an all denim outfits for the 2001 AMA's?
Justin Timberlake and Britney Spears
What city is referenced in the album 1989?
New York City
Who was the first woman to be Vice President of the United States?
Kamala Harris
Who was the first Person of Color named as Sexiest Man Alive in 1996?
Denzel Washington
What Rom Com is this quote from?
“But mostly, I hate the way I don’t hate you. Not even close."
10 Things I Hate About You (1999)
What is Nick Jonas and Priyanka Chopra's age difference?
10 years
Taylor Swift made a cameo in what TV show? (bonus points if you can name the episode/her role)
New Girl (Cece and Shivrang's wedding day, she and Shivrang ran away together)
Who was the first woman to win a Nobel Prize?
Marie Curie
Which Marvel star won Sexiest Man Alive in 2014?
Chris Hemsworth
What Rom Com is this quote from?
"To me, you are perfect."
Love Actually
On what movie set did Freddie Prinze Jr and Michelle Gellar meet?
I Know What You Did Last Summer
Which album did Taylor Swift write by herself, with no co-writers?
Speak Now
Who was the first female Supreme Court Justice in the U.S.?
Sandra Day O'Connor
Who became the oldest Sexiest Man Alive winner at age 57?
Patrick Dempsey
What Rom Com is this quote from?
“I’m not asking you to marry me. I’m asking you to do me a favor.”
Leap Year (2010)
Which celebrity couple starred together in Mr. & Mrs. Smith?
Brad Pitt and Angelina Jolie
What two actors are featured in the All Too Well short film?
Sadie Sink and Dylan O'Brien
Which woman was the first to fly solo across the Atlantic Ocean?
Amelia Earhart
Who was the couple honored (instead of a singular person) in 1998 People Magazine?
Richard Gere and Cindy Crawford
What Rom Com is this quote from?
"But our love... It's like the wind. I can't see it, but I can feel it."
A Walk to Remember (2002)
What was the first romantic comedy won the award for Best Picture?
It Happened One Night (1934)
What classic book is referenced in “This Is Why We Can’t Have Nice Things”?
The Great Gatsby by F. Scott Fitzgerald
Who was the first woman to direct a film that won Best Picture at the Oscars?
Kathryn Bigelow