I have the same problem. One idea I had was that one character asks the other character, "how long will this take?" The other character answers, and we switch scenes to "later." In my story, it's long-distance travel, so the character will ask how much farther they have to walk.
The other option is to brainstorm conflicts and roadblocks that crop up during that time. Although, I'm afraid of what I call "Space Camp" syndrome - in the movie "Space Camp," so many EPIC things went wrong that it started to get ridiculous and not at all believable. We want conflict, but believable conflict. So if I go this route, I plan to keep it believable by keeping the conflicts small, with the sole purpose of advancing my plots and developing the two characters involved such that they support those plots.
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