Whether you depict cities or meals or boyfriends, keep them brief and compress them together. When the montage ends we’ll arrive at an actual scene, but with the sense that considerable time has passed. Another method to imply time passing is intercutting. End one scene and jump to a flashback, alternating between the past and present. That way, when you jump back to the present you won’t have to arrive at the moment you left off. Each jump allows you to fudge time, implying it’s passed. Or you can intercut between characters. Think of the various plot threads in John Berendt’s Midnight in the
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