Clooney was first photographed with Alamuddin in October in London, where the two shared a bite at Berners Tavern – and a cab ride – together. The two were discussing a satellite program over Syria, Clooney's rep said at the time. By the holidays, according to a source, Alamuddin was a guest of Clooney's during a vacation to Los Cabos with his pals, including longtime friend and Casamigos Tequila business partner Rande Gerber and his wife, Cindy Crawford.
The two kept a low profile until after Valentine's Day, when Alamuddin joined Clooney for a special White House screening on Feb. 18 of his film The Monuments Men. The couple held hands at the event with President Barack Obama. After, the duo joined Clooney's costars Matt Damon and Bill Murray at Willard Hotel's Round Robin & Scotch Bar, where, an onlooker told PEOPLE, they were stuck like glue.
Days later, the couple landed in N.Y.C., where they stayed at Manhattan's Carlyle Hotel and dined at French restaurant Rotisserie Georgette with Gerber and another of Clooney's Casamigos business partners, real estate developer Mike Meldman.
On March 27 they turned up on the West Coast at another dinner table with friends. This time, they feasted on Japanese with Clooney's friends John Krasinski and wife Emily Blunt at Kazu Sushi in Studio City, Calif.
Almost a month later, they were ready to show off their big news. On Wednesday they were spotted at L.A. restaurant Craig's with friends, with Alamuddin wearing a huge ring, and the following night they met up with Gerber and Crawford at Nobu in Malibu.
Of the engagement, a source tells PEOPLE, "George and Amal are trying to keep things very low-key, but they also aren't really trying to hide this, it doesn't seem. I think it's like they want the people they love to know that this is real, that they plan on being together forever."