08/19/2026
That $400 in Southwest credit was about to expire. I almost let it.
Instead I called Jerry at work and asked if he wanted to use it on Cabo. He said yes before I even finished asking.
We hadn’t been back since our first trip together in 1990, two years before we got married. Then life happened. Marriage, jobs, kids, and a running idea that Mexico wasn’t safe to visit.
That $400 broke the streak. We’ve gone back every single year since.
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