Inside Jen Aniston's strong bond with Sandra Bullock and Bryan Randall

Best friends Sandra Bullock and Jennifer Aniston aren’t strangers to double dating! The A-listers became close about five years ago, multiple insiders reveal exclusively in the new issue of Us Weekly. Early on in their friendship, the duo loved to go out with Bullock’s boyfriend, Bryan Randall, and Aniston’s then-husband Justin Theroux before the latter couple ended their two-year marriage in late 2017.

“Sandy felt comfortable enough to bring Bryan to Jen and Justin’s wedding” in 2015, a source tells Us. Theroux, 47, and Randall, 53, “got along great,” adds the Aniston insider. “The four of them would often do things as couples,” including hitting up Bullock’s Bess Bistro in Austin, Texas, with the then-newlyweds in September 2015.

39 PHOTOS
Sandra Bullock out and about
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Sandra Bullock out and about
NEW YORK, NY - DECEMBER 17: Sandra Bullock attends the 'Bird Box' New York Screening at Alice Tully Hall, Lincoln Center on December 17, 2018 in New York City. (Photo by Theo Wargo/WireImage)
BERLIN, GERMANY - NOVEMBER 27: Sandra Bullock attends the European premiere of the film 'Bird Box' at Zoo Palast on November 27, 2018 in Berlin, Germany. (Photo by Andreas Rentz/Getty Images for Netflix)
SAO PAULO, BRAZIL - DECEMBER 09: Sandra Bullock signs autographs at Comic-Con São Paulo on December 9, 2018 in Sao Paulo, Brazil. (Photo by Alexandre Schneider/Getty Images for Netflix)
NEW YORK, NY - DECEMBER 17: Sandra Bullock arrives at 'The Late Show with Stephen Colbert' at the Ed Sullivan Theater on December 17, 2018 in New York City. (Photo by Raymond Hall/GC Images)
LONDON, ENGLAND - JUNE 13: Sandra Bullock attends the 'Ocean's 8' UK Premiere held at Cineworld Leicester Square on June 13, 2018 in London, England. (Photo by Jeff Spicer/FilmMagic)
LONDON, ENGLAND - JUNE 13: Sandra Bullock attends the 'Ocean's 8' UK Premiere held at Cineworld Leicester Square on June 13, 2018 in London, England. (Photo by Jeff Spicer/FilmMagic)
LOS ANGELES - JUNE 7: The Late Late Show with James Corden airing Thursday, June 7, 2018, with guests Sandra Bullock, Sarah Paulson, and Awkwafina. (Photo by Terence Patrick/CBS via Getty Images)
TODAY -- Pictured: Hoda Kotb, Sandra Bullock, Gesine Bullock-Prado and Jenna Bush Hager on Tuesday, June 5, 2018 -- (Photo by: Nathan Congleton/NBC/NBCU Photo Bank via Getty Images)
NEW YORK, NY - JUNE 05: Sarah Paulson (L) and Sandra Bullock attend the 'Ocean's 8' World Premiere at Alice Tully Hall on June 5, 2018 in New York City. (Photo by Michael Stewart/WireImage)
NEW YORK, NY - JUNE 05: Sandra Bullock attends the world premiere of 'Ocean's 8' at Alice Tully Hall at Lincoln Center on June 5, 2018 in New York City. (Photo by Taylor Hill/Getty Images)
JIMMY KIMMEL LIVE: GAME NIGHT - 'Jimmy Kimmel Live: Game Night' special edition episodes air in primetime every night of the NBA Finals. The guest for Sunday, June 3 included Sandra Bullock ('Ocean's 8'). (Randy Holmes/ABC via Getty Images) SANDRA BULLOCK
TODAY -- Pictured: Hoda Kotb and Sandra Bullock on Tuesday, May 22, 2018 -- (Photo by: Nathan Congleton/NBC/NBCU Photo Bank via Getty Images)
NEW YORK, NY - MAY 24: Sandra Bullock is seen leaving her hotel on May 24, 2018 in New York, New York. (Photo by Alessio Botticelli/GC Images)
NEW YORK, NY - MAY 22: Sandra Bullock is seen on May 22, 2018 in New York City. (Photo by Raymond Hall/GC Images)
NEW YORK, NY - MAY 22: (L-R) Sarah Paulson, Awkwafina, Sandra Bullock, Cate Blanchett, Anne Hathaway and Mindy Kalling attend the 'Ocean's 8' worldwide photo call at The Metropolitan Museum of Art on May 22, 2018 in New York City. (Photo by Daniel Zuchnik/FilmMagic)
BEVERLY HILLS, CA - MAY 03: Actress Sandra Bullock speaks during the Beverly Hills Bar Association's 2018 Entertainment Lawyer of the Year Dinner at the Montage Beverly Hills on May 3, 2018 in Beverly Hills, California. (Photo by Frederick M. Brown/Getty Images)
LAS VEGAS, NV - APRIL 24: (L-R) Actresses Sarah Paulson, Mindy Kaling, Sandra Bullock, Cate Blanchett, Anne Hathaway and actress/rapper Awkwafina attend CinemaCon 2018 Warner Bros. Pictures Invites You to The Big Picture, an Exclusive Presentation of our Upcoming Slate at The Colosseum at Caesars Palace during CinemaCon, the official convention of the National Association of Theatre Owners on April 24, 2018 in Las Vegas, Nevada. (Photo by Gabe Ginsberg/Getty Images)
HOLLYWOOD, CA - MARCH 04: Sandra Bullock arrives at the 90th Annual Academy Awards at Hollywood & Highland Center on March 4, 2018 in Hollywood, California. (Photo by Steve Granitz/WireImage)
NEW YORK, NY - JANUARY 24: Sandra Bullock seen at the 'Ocean's Eight' film set in Central Park on January 24, 2017 in New York City. (Photo by Robert Kamau/GC Images)
NEW YORK, NY - DECEMBER 03: Sandra Bullock is seen filming 'Ocean's 8' on December 3, 2016 in New York City. (Photo by Alessio Botticelli/FilmMagic)
NEW YORK, NY - DECEMBER 03: Sandra Bullock seen on December 3, 2016 in New York City. (Photo by Raymond Hall/GC Images)
NEW YORK, NY - NOVEMBER 07: Sandra Bullock, Cate Blanchett and Rihanna are seen filming 'Ocean's 8' in Central Park on November 7, 2016 in New York City. (Photo by Raymond Hall/GC Images)
NEW YORK, NY - OCTOBER 31: Sandra Bullock and Cate Blanchett are seen filming 'Ocean's 8' on October 31, 2016 in Queens borough of New York City. (Photo by Alessio Botticelli/GC Images)
NEW YORK, NY - OCTOBER 24: Actress Sandra Bullock (R) and Cate Blanchett are seen on the set of 'Ocean's Eight' on October 24, 2016 in New York City. (Photo by Raymond Hall/GC Images)
LOS ANGELES, CA - JANUARY 06: Actress Sandra Bullock accepts the Favorite Movie Actress award onstage during the People's Choice Awards 2016 at Microsoft Theater on January 6, 2016 in Los Angeles, California. (Photo by Lester Cohen/WireImage)
LOS ANGELES - JANUARY 6: Sandra Bullock and Melissa McCarthy backstage at the PEOPLE'S CHOICE AWARDS 2016, from the Microsoft Theater on Wednesday, Jan. 6, 2016 (9:00-11:00 PM, live ET/delayed PT) on the CBS Television Network. (Photo by Francis Specker/CBS via Getty Images)
NEW YORK - OCTOBER 29: Sandra Bullock seen out in Manhattan on October 29, 2015 in New York, New York. (Photo by Josiah Kamau/BuzzFoto via Getty Images)
NEW YORK, NY - OCTOBER 29: Sandra Bullock is seen heading to Today TV Show on October 29, 2015 in New York City. (Photo by Alessio Botticelli/GC Images)
THE TONIGHT SHOW STARRING JIMMY FALLON -- Episode 0355 -- Pictured: Actress Sandra Bullock on October 28, 2015 -- (Photo by: Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images)
NEW YORK, NY - OCTOBER 28: Sandra Bullock Visits 'The Tonight Show Starring Jimmy Fallon' at Rockefeller Center on October 28, 2015 in New York City. (Photo by Theo Wargo/NBC/Getty Images for 'The Tonight Show Starring Jimmy Fallon')
HOLLYWOOD, CA - OCTOBER 26: Actress Sandra Bullock attends the premiere of 'Our Brand Is Crisis' at TCL Chinese Theatre on October 26, 2015 in Hollywood, California. (Photo by Jason LaVeris/FilmMagic)
HOLLYWOOD, CA - OCTOBER 26: Actress Sandra Bullock arrives at the premiere of Warner Bros. Pictures' 'Our Brand Is Crisis' at TCL Chinese Theatre on October 26, 2015 in Hollywood, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
BEVERLY HILLS, CA - OCTOBER 17: Sandra Bullock at the 'Our Brand Is Crisis' Press Conference at the Four Seasons Hotel on October 17, 2015 in Beverly Hills, California. (Photo by Vera Anderson/WireImage)
TORONTO, ON - SEPTEMBER 12: Actresses Sandra Bullock (L) and Zoe Kazan attend the 'Our Brand Is Crisis' press conference at the 2015 Toronto International Film Festival at TIFF Bell Lightbox on September 12, 2015 in Toronto, Canada. (Photo by Jason Merritt/Getty Images)
TORONTO, ON - SEPTEMBER 12: Actress/producer Sandra Bullock speaks onstage during the 'Our Brand Is Crisis' press conference at the 2015 Toronto International Film Festival at TIFF Bell Lightbox on September 12, 2015 in Toronto, Canada. (Photo by George Pimentel/WireImage)
TORONTO, ON - SEPTEMBER 12: (L-R) Executive Producer/actress Sandra Bullock, Producer Grant Heslov and actress Zoe Kazan attend EW's Must List Party during the 2015 Toronto International Film Festival at Thompson Hotel on September 12, 2015 in Toronto, Canada. (Photo by John Shearer/Getty Images for Entertainment Weekly)
TORONTO, ON - SEPTEMBER 11: Actress Sandra Bullock attends the 'Our Brand is Crisis' premiere during the 2015 Toronto International Film Festival at the Princess of Wales Theatre on September 11, 2015 in Toronto, Canada. (Photo by Jason Merritt/Getty Images)
TORONTO, ON - SEPTEMBER 11: Actress Sandra Bullock attends the 'Our Brand is Crisis' premiere during the 2015 Toronto International Film Festival at the Princess of Wales Theatre on September 11, 2015 in Toronto, Canada. (Photo by Jason Merritt/Getty Images)
TORONTO, ON - SEPTEMBER 11: Executive Producer/Actress Sandra Bullock (L) and Producer George Clooney arrive to the 'Our Brand Is Crisis' photo call at Princess of Wales Theatre on September 11, 2015 in Toronto, Canada. (Photo by John Shearer/WireImage)
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The ladies have helped each other through hard times too. Whether it was divorce or the loss of a parents, they have stuck together. “Sandra was there when Jen and Justin got divorced,” says the source. “She was someone Jen could lean on.” Though Aniston, 50, wasn’t in the picture when Bullock, 54, endured a devastating split from husband Jesse James in 2010, she was there for her friend when Bullock’s father and two dogs died within weeks of one another last fall.

“Jen was extremely thoughtful when Sandy’s dad passed away,” adds the insider, likely because she’d lost her mom — with whom she had a famously difficult relationship — just two years earlier. “They’ve bonded because they each had complicated relationships with a parent.”

After the Friends actress and The Leftovers actor split, dinners continued with the model-turned-photographer. “The dynamic hasn’t changed, even though Justin isn’t around anymore,” continues the insider, adding that the Murder Mystery star “adores” Randall. “Jen, Sandra and Bryan still hang out the same way they always have. They all just click and have a strong friendship. Jen counts Sandra and Bryan as close friends she loves to have around.”

27 PHOTOS
Justin Theroux and Jennifer Aniston together
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Justin Theroux and Jennifer Aniston together
HOLLYWOOD, CA - JULY 26: Jennifer Aniston and Justin Theroux attend the ceremony honoring Jason Bateman with Star On The Hollywood Walk Of Fame on July 25, 2017 in Hollywood, California. (Photo by JB Lacroix/WireImage)
HOLLYWOOD, CA - JULY 26: Jennifer Aniston and Justin Theroux attend the ceremony honoring Jason Bateman with Star On The Hollywood Walk Of Fame on July 25, 2017 in Hollywood, California. (Photo by JB Lacroix/WireImage)
PARIS, FRANCE - APRIL 13: Justin Theroux and Jennifer Aniston attend the Festival Serie Mania Opening Night, at Le Grand Rex on April 13, 2017 in Paris, France. (Photo by Stephane Cardinale - Corbis/Corbis via Getty Images)
Jennifer Aniston and Justin Theroux seen leaving Chanel store in Paris on April 12, 2017. (Photo by Mehdi Taamallah/NurPhoto via Getty Images)
PARIS, FRANCE - APRIL 11: Actor Justin Theroux and Actress Jennifer Aniston attend the 'LVxKOONS' exhibition (Louis Vuitton and Jeff Koons Collaboration) at Musee du Louvre on April 11, 2017 in Paris, France. (Photo by Bertrand Rindoff Petroff/Getty Images)
PARIS, FRANCE - APRIL 11: (L-R) Justin Theroux and Jennifer Aniston attend the Louis Vuitton's Dinner for the Launch of Bags by Artist Jeff Koons at Musee du Louvre on April 11, 2017 in Paris, France. (Photo by Stephane Cardinale - Corbis/Corbis via Getty Images)
LOS ANGELES, CA - APRIL 04: Actor Justin Theroux and actress Jennifer Aniston attend the season 3 premiere of 'The Leftovers' at Avalon Hollywood on April 4, 2017 in Los Angeles, California. (Photo by Jason LaVeris/FilmMagic)
BEVERLY HILLS, CA - FEBRUARY 26: Actors Jennifer Aniston and Justin Theroux arrive at the 2017 Vanity Fair Oscar Party Hosted By Graydon Carter at Wallis Annenberg Center for the Performing Arts on February 26, 2017 in Beverly Hills, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
HOLLYWOOD, CA - FEBRUARY 26: Actors Jennifer Aniston (L) and Justin Theroux pose backstage during the 89th Annual Academy Awards at Hollywood & Highland Center on February 26, 2017 in Hollywood, California. (Photo by Christopher Polk/Getty Images)
NEW YORK, NY - SEPTEMBER 28: Justin Theroux and Jennifer Aniston seen on the streets of Manhattan on September 28, 2016 in New York City. (Photo by James Devaney/GC Images)
NEW YORK, NY - SEPTEMBER 24: Jennifer Aniston and Justin Theroux step out for dinner in Manhattan on September 24, 2016 in New York City. (Photo by Robert Kamau/GC Images)
NEW YORK, NY - JUNE 21: Jennifer Aniston and Justin Theroux seen out on June 21, 2016 in New York City. (Photo by Robert Kamau/GC Images)
NEW YORK, NY - JUNE 19: Jennifer Aniston and Justin Theroux are seen in Midtown on June 19, 2016 in New York City. (Photo by Alo Ceballos/GC Images)
Jennifer Aniston and Justin Theroux attend the 'Zoolander 2' world premiere at Alice Tully Hall in New York City. ?? LAN (Photo by Lars Niki/Corbis via Getty Images)
SANTA MONICA, CA - JANUARY 17: Actors Jennifer Aniston and Justin Theroux arrive at the 21st Annual Critics' Choice Awards at Barker Hangar on January 17, 2016 in Santa Monica, California. (Photo by Gregg DeGuire/WireImage)
SANTA MONICA, CA - JANUARY 17: Actor Justin Theroux (L) and actress Jennifer Aniston attend the 21st Annual Critics' Choice Awards at Barker Hangar on January 17, 2016 in Santa Monica, California. (Photo by Tiffany Rose/Getty Images for Santa Margherita, Heineken and Proximo Spirits)
SANTA MONICA, CA - JANUARY 17: Justin Theroux, Will Forte and Jennifer Aniston attend the 21st Annual Critics' Choice Awards at Barker Hangar on January 17, 2016 in Santa Monica, California. (Photo by Kevin Mazur/WireImage)
NEW YORK, NY - NOVEMBER 16: Justin Theroux and Jennifer Aniston attend the Celebrity Charades Goes Medieval Gala 2015 at Capitale on November 16, 2015 in New York City. (Photo by Randy Brooke/WireImage)
AUSTIN, TX - OCTOBER 03: Actors Justin Theroux and Jennifer Aniston attend HBO's 'The Leftovers' Season 2 Premiere at Paramount Theatre on October 3, 2015 in Austin, Texas. (Photo by C Flanigan/WireImage)
HOLLYWOOD, CA - FEBRUARY 22: Actors Justin Theroux (L) and Jennifer Aniston attend the 87th Annual Academy Awards at Hollywood & Highland Center on February 22, 2015 in Hollywood, California. (Photo by Jason Merritt/Getty Images)
BEVERLY HILLS, CA - FEBRUARY 22: Actors Justin Theroux (L) and Jennifer Aniston attend the 2015 Vanity Fair Oscar Party hosted by Graydon Carter at Wallis Annenberg Center for the Performing Arts on February 22, 2015 in Beverly Hills, California. (Photo by Alberto E. Rodriguez/WireImage)
LOS ANGELES, CA - JANUARY 25: Justin Theroux and Jennifer Aniston attend the 21st Annual Screen Actors Guild Awards at the Shrine Auditorium on January 25, 2015 in Los Angeles, California. (Photo by Amy Graves/WireImage)
LOS ANGELES, CA - JANUARY 25: Actors Justin Theroux (L) and Jennifer Aniston attend the 21st Annual Screen Actors Guild Awards at The Shrine Auditorium on January 25, 2015 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)
LOS ANGELES, CA - JANUARY 15: Actors Justin Theroux and Jennifer Aniston arrive at the 20th Annual Critics' Choice Movie Awards at Hollywood Palladium on January 15, 2015 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
LOS ANGELES, CA - JANUARY 15: (EXCLUSIVE COVERAGE) Actors Justin Theroux (L) and Jennifer Aniston attend the 20th annual Critics' Choice Movie Awards at the Hollywood Palladium on January 15, 2015 in Los Angeles, California. (Photo by Jason Kempin/Getty Images for A&E Network)
BEVERLY HILLS, CA - JANUARY 11: Actor Justin Theroux and actress Jennifer Aniston attend HBO's post Golden Globe Awards party at The Beverly Hilton Hotel on January 11, 2015 in Beverly Hills, California. (Photo by Jason LaVeris/FilmMagic)
BEVERLY HILLS, CA - JANUARY 11: Actor Justin Theroux and actress Jennifer Aniston arrive at the 16th Annual Warner Bros. And InStyle Post-Golden Globe Party at The Beverly Hilton Hotel on January 11, 2015 in Beverly Hills, California. (Photo by Jon Kopaloff/FilmMagic)
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