Rule 058 | Vacationing Apart Is Okay If The Destination Stinks

Is traveling separately (with friends) always worth the trip? The Peppers continue their Summer Travel Series by diving into the topic of vacationing apart, but neither person seems to know how to balance out their adventures. They both feel a little guilty for exploring new places without the other, and Gerard finally makes a decision to go on the big boat trip he’s been hoping for.

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  • A longtime friend and listener of the show (Hi, Santos!) mentions to Gerard that he’s got a Guys Trip in the works. Brainstorming ensues and Mardi Gras beads are officially thrown out the window.

  • Jessie immediately gets FOMO and the couple decides that the trick to prevent this is to choose a city that the other partner is not interested in visiting.

  • Gerard went to Las Vegas for March Madness earlier this year and The Peppers realize that this definitely counts as an official Guy's Trip... Especially because it helped G meet his yearly quota for basketball watching AND meat eating in just a couple of days. 

  • Jessie’s past speaking schedule has allowed her to experience a handful of accidental Girl’s Trips and she's always up for the chance to combine fun with an extra dose of productivity.

  • The Peppers try to uncover truth: Do parents need separate travel time more than non-parents? The verdict is still out but this kidless couple already has a few upcoming adventures on the books.

  • Gerard admits that he needs guy time to keep their marriage healthy. The Peppers agree that pursuing outside friendships is a good way to disperse the burden of our individual friendship needs.

  • Talking about cost and stressing about money might actually take away from the benefits of travel. The last time Jessie went on a girls trip was around the same time that our budgeting episode went live, and the timing of these two things actually makes a lot of sense based on our goals.

  • The Peppers realize that financial planning can actually provide more freedom than financial restrictions. (This is basically exactly what Jessie was trying to implement in Episode 57.)

  • Jessie is going on a Women’s Retreat with Morgan in the Fall and she thinks that Gerard should go on the Sailing Trip with Zac.



  1. Who are the top three people you’d bring on a friends trip if your partner was going to stay at home?

  2. Do you get to spend enough time with friends when your partner isn't around?

  3. Have you ever felt jealous of your spouse because of a time that they’ve gotten to travel with their friends? Or guilt if you’re the one who is getting to experience it?

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