1.
Jennifer Garner attended her first red carpet alongside Scott Foley in 1999. At the time, the duo had been dating since 1998 and were eventually married for three years from 2000 to 2003.
3.
Beyoncé attended her first red carpet event in 1998 alongside Kelly Rowland, LeToya Luckett, and LaTavia Robertson.
4.
Ryan Reynolds attended one of his first red carpet events with Traylor Howard in 1999. At the time, Ryan and Traylor were reportedly dating for a brief period while starring together on the ABC sitcom Two Guys and a Girl.
5.
Samuel L. Jackson attended one of his earliest red carpets with LaTanya Richardson Jackson in 1993. The duo got married in 1980 and have been together ever since.
6.
Chris Evans attended his first red carpet event alongside Jessica Biel in 2001. The duo reportedly dated for a little while in the early 2000s.
7.
Julia Roberts walked several of her first red carpets in 1989 alongside Dylan McDermott. The duo dated for a brief period in the late ’80s after starring in Steel Magnolias together.
8.
Leonardo DiCaprio walked his first red carpet alongside his mom in 1993.
9.
Cher walked one of her first Hollywood red carpets alongside Sonny Bono in 1973. The duo were married from 1964 to 1975.
10.
Oprah walked her first big red carpet alongside Stedman Graham in 1987. The duo started dating in 1986 and have been together ever since.
11.
Reese Witherspoon walked one of her earliest red carpets alongside Chris O’Donnell in 1993. The two reportedly dated for a few months, but neither ever confirmed the relationship.
12.
Jennifer Lopez walked her first movie premiere red carpet in 1995 alongside David Cruz, her then-boyfriend who she had been dating since high school.
13.
Jennifer Aniston attended her first red carpet event in 1990 alongside Charlie Schlatter. They dated while they were starring together on the short-lived sitcom Ferris Bueller.
14.
Courteney Cox walked the red carpet alongside her then-boyfriend Paul Brown in 1987. They reportedly only dated for about a year.
15.
Christina Applegate attended one of her first red carpet events alongside Matthew Perry in 1988. The duo had just starred together in the TV movie, Dance ’til Dawn.
16.
Gabrielle Union attended one of her first red carpet events in 1998 alongside Dulé Hill. The duo went on to star in She’s All That together in 1999.
17.
Tom Cruise walked his first notable red carpet alongside Heather Locklear in 1982. In 2013, Heather revealed it was their “first and last” date.
18.
Keanu Reeves attended one of his first red carpets in 1989 alongside Winona Ryder. The duo have been good friends for years and eventually went on to star in countless movies together, staring with Dracula in 1992.
19.
Kaley Cuoco attended her first red carpet premiere in 2002 alongside David Gallagher. The duo became friends after Kaley appeared on 7th Heaven.
20.
Dolly Parton attended her first Hollywood red carpet event alongside Lily Tomlin and Jane Fonda in 1980.
21.
Jessica Chastain walked the red carpet alongside Michael Urie in 2007. They had attended Julliard around the same time and starred in a play together in 2003.
22.
Linda Cardellini attended her first red carpet premiere in 1999 alongside Busy Philipps. The duo starred together on the short-lived, but beloved, comedy Freaks and Geeks.
23.
Angela Bassett walked her first red carpet alongside Wren T. Brown in 1993. The duo starred together in The Heroes of Desert Storm in 1991 and went on to star in Waiting to Exhale in 1995.
24.
Meryl Streep and her husband Don Gummer walked their first red carpet together in 1979. The duo have been married since 1978.
25.
And finally, Miley Cyrus attended her first big press event alongside her dad Billy Ray Cyrus in 2006. Of course, they were both starring in Hannah Montana at the time.
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