Episode Details

How to make girls trips, weekend getaways, and friendship travel actually happen

This week, I’m joined by one of my favorite people to talk to about friendship on and off the microphone: my assistant producer and friend, Rebekah Jacobs!

We're discussing something she does far more often than I do—traveling with friends. Rebekah is a frequent girls-trip traveler. She’s the friend who is always hopping on a plane, meeting friends for a weekend away, or squeezing in a 24-hour getaway. Meanwhile, I realized while preparing for this episode that I’ve traveled with friends far less often than most people might assume, especially for someone who talks about friendship for a living. 

Together, we unpack why friendship travel can feel so difficult to pull off, especially during busy seasons of life. We talk about kids, schedules, money, logistics, guilt, and the challenge of finding a date that works for everyone. But we also talk about why it’s worth the effort.

In this episode, we discuss:

• Why you don’t need a big friend group to take a friendship trip (one-on-one is great too!)
• How to finally move a trip from “We should do that sometime” to an actual date on the calendar
• Rebekah’s advice about being the “bendy friend” when schedules get complicated
• What happens when different people want different things from the same trip
• How to navigate money conversations without resentment
• Why self-advocacy is an underrated travel skill
• The importance of putting your phone away and being present
• How trips help deepen friendships in ways everyday life often can’t

One takeaway I especially loved

Rebekah said something during our conversation that I haven’t stopped thinking about: the worth-it bar is lower than you think.

In other words, stop waiting for the perfect destination, the perfect budget, the perfect schedule, or the perfect group. If you can make one night work, do it. If all you can manage is 24 hours, take the 24 hours. 

Links Mentioned

• Tickets to Dear Nina LIVE in Excelsior, Minnesota on July 29
• The White Lotus episode: Lessons from the White Lotus Friendship Trio
• The 2025 live show: From the Cafeteria to the Mahj Table: Friend Group Challenges from Teens to Midlife and Beyond
• The Beaches episode! What “Beaches” Gets Right About Friendship: Professors Paul Eastwick & Eli Finkel (of The Love Factually Podcast)
• Article on Jane Pratt's Substack: "Girls Trips Always Make Me Feel Left Out, Disappointed and Depressed"

As always, thank you for listening. And if this episode inspires you to finally book that trip you've been talking about for years, I'd love to hear about it. Safe travels!

ALL THE DEAR NINA LINKS + CONTACT INFO

!! Catch up on all Dear Nina episodes on Apple and Spotify

📢 How to prom