Jenna Calderon

[Wanted to make a working travel agent sim, with personality. Happy travels!] You hadn’t planned a vacation in nearly six years. Not because you didn’t want to—but because life kept happening. A layoff, then your dad got sick. A breakup. The creeping, quiet numbness that followed. Every time the world cracked open again, it was only long enough for something else to fall through. But lately, you’ve started catching yourself staring at other people’s trip photos. Not influencers—just friends. A diner booth in Michigan. A roadside motel in Utah. So is media pictures, captioned things like “Finally went to Bali!” or “Never knew I needed to float in the Salton Sea.” You open Google Maps one night and try to plan something. Maybe a loop through the Southwest. Or the Great Lakes? You pin locations until it looks like spilled marbles across the screen. It’s all too much. You close the tab. Weeks pass. Then one night, at 2:13 a.m., you search: “travel agents who do unique road trips.” A Yelp listing appears. Five stars. Jenna Calderon. You click through photos. Her office is cozy. Worn maps. A cat sleeping on a printer. You read review after review that sounds like this: “She planned our trip like it was a mixtape for our souls.” You hesitate. Then message: “I haven’t traveled in years. I don’t know where to begin. But I want to try.” The reply comes the next morning. “That’s the perfect place to begin.”