#199 - Traveling with Friends: Lessons From a Girls-Trip Regular (Rebekah Jacobs)

What this episode covers

Traveling with friends sounds great in theory. Actually making it happen? That's the hard part. This week, I'm joined by my assistant producer and friend, Rebekah Jacobs, to talk about girls trips, weekend getaways, and why friendship travel is worth the effort. Rebekah is someone who regularly hops on a plane to spend time with friends, while I've traveled with friends far less often than most people might assume. We discuss the obstacles that keep many of us from taking friendship trips—busy schedules, parenting responsibilities, finances, logistics, and guilt—and how to work around them. Rebekah shares practical advice about being the "bendy friend," navigating different travel styles, talking honestly about budgets, and finally getting a trip from the group text to the calendar. Whether you're planning a girls trip, a one-on-one getaway, or simply trying to spend more meaningful time with friends, this episode is a reminder that the "worth it" bar is lower than you think. Sometimes one night away is enough to create memories that strengthen a friendship for years to come. ✈️💕 I like this version because it sounds like you, includes the major keywords (traveling with friends, girls trips, friendship travel), and captures the dynamic between you and Rebekah, which is one of the most enjoyable parts of the episode. now using the show notes, write the youtube description and use emojis where appropriate and make the bullet points copy and pastable ✈️ Traveling with Friends: Why It's Worth the Effort How to make girls trips, weekend getaways, and friendship travel actually happen Traveling with friends sounds wonderful in theory—but actually making it happen can feel impossible. In this episode of Dear Nina: Conversations About Friendship, I’m joined by my assistant producer and friend, Rebekah Jacobs, to talk about friendship travel, girls trips, weekend getaways, and why these experiences are often worth far more than the effort it takes to plan them. Rebekah is the friend who is always hopping on a plane to see friends, while I've traveled with friends far less often than many people might expect. Together, we discuss the real barriers that keep adults from traveling with friends—including busy schedules, parenting responsibilities, finances, logistics, and guilt—and how to work through them. We also talk about why you don't need a huge friend group, a luxury destination, or a week-long vacation to create meaningful memories with friends. Sometimes one night away is enough. ❤️ In this episode: 📅 How to finally move a trip from "We should do that sometime" to an actual date on the calendar 👯 Why you don't need a big friend group to take a friendship trip 🌟 Rebekah's advice about being the "bendy friend" 💰 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 shared experiences deepen friendships ✈️ Why the "worth-it" bar is lower than you think Links Mentioned 🎟️ Dear Nina LIVE in Excelsior, Minnesota (July 29): [insert link] 🌺 The White Lotus Friendship Trio Episode: [insert link] 🎤 From the Cafeteria to the Mahj Table (Live Chicago Show): [insert link] 🏖️ What Beaches Gets Right About Friendship (with Love, Factually): [insert link] 📰 Jane Pratt Substack article: "Girls Trips Always Make Me Feel Left Out, Disappointed and Depressed" Connect with Dear Nina 💌 Newsletter: https://dearnina.substack.com 📸 Instagram: https://instagram.com/dearninafriendship 🎵 TikTok: https://tiktok.com/@dearninafriendship 👥 Facebook Group: Dear Nina, The Group If this episode inspires you to finally book that trip you've been talking about for years, I'd love to hear about it. Where would you go? Let me know in the comments. 👇 #Friendship #GirlsTrip #TravelingWithFriends #FriendshipAdvice #AdultFriendships #DearNina #WomensFriendships #GirlsWeekend #TravelTips #FriendshipPodcast #RebekahJacobs #TravelWithFriends #FriendshipTravel #WomenSupportingWomen #WeekendGetaway I agree. For your audience and brand, I'd use emojis sparingly—more as visual breaks than decoration. YouTube Description Traveling with Friends: Why It's Worth the Effort How to make girls trips, weekend getaways, and friendship travel actually happen Traveling with friends sounds wonderful in theory—but actually making it happen can feel impossible. In this episode of Dear Nina: Conversations About Friendship, I'm joined by my assistant producer and friend, Rebekah Jacobs, to talk about friendship travel, girls trips, weekend getaways, and why these experiences are often worth far more than the effort it takes to plan them. Rebekah is the friend who is always hopping on a plane to see friends, while I've traveled with friends far less often than many people might expect. Together, we discuss the real barriers that keep adults from traveling with friends—including busy schedules, parenting responsibilities, finances, logistics, and guilt—and how to work through them. We also talk about why you don't need a huge friend group, a luxury destination, or a week-long vacation to create meaningful memories with friends. Sometimes one night away is enough. In this episode: • 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 Links Mentioned 🎟️ Dear Nina LIVE in Excelsior, Minnesota on July 29: [link] 🎙️ The White Lotus episode: Lessons from the White Lotus Friendship Trio [link] 🎙️ The 2025 live show: From the Cafeteria to the Mahj Table: Friend Group Challenges from Teens to Midlife and Beyond [link] 🎙️ The Beaches episode: What Beaches Gets Right About Friendship with Paul Eastwick & Eli Finkel [link] 📰 Jane Pratt's Substack article: "Girls Trips Always Make Me Feel Left Out, Disappointed and Depressed" 📬 Newsletter: https://dearnina.substack.com 📸 Instagram: @dearninafriendship If this episode inspires you to finally book that trip you've been talking about for years, I'd love to hear about it in the comments. #Friendship #TravelingWithFriends #GirlsTrip #AdultFriendships #FriendshipPodcast #DearNina #FriendshipAdvice #GirlsWeekend #WomenAndFriendship This feels much closer to your style: warm, professional, and not trying to look like a lifestyle influencer's caption. how about this title: "Friendship Travel: Lessons from a Girls-Trip Regular" I like it, but I think it works better as a newsletter or blog title than a podcast episode title. My hesitation is that "girls-trip regular" is a clever phrase, but it's not something people search for. If someone is browsing Apple Podcasts, Spotify, or YouTube, they're more likely to search for: traveling with friends girls trips friendship travel trips with friends adult friendship So from an SEO/discoverability standpoint, I'd rather keep one of those terms front and center. Some variations: Friendship Travel: Advice from a Girls-Trip Regular Keeps your phrase but adds a clearer benefit. Friendship Travel: What a Girls-Trip Regular Knows More curiosity-driven. Traveling with Friends: Lessons from a Girls-Trip Regular My favorite version if you want to keep the phrase. Strong SEO plus personality. Girls Trips and Friendship Travel: Lessons from a Frequent Traveler Very searchable. Traveling with Friends: What a Girls-Trip Regular Has Learned Feels conversational and fits the episode's dynamic. Of all the options we've discussed, I still think: Traveling with Friends: Why It's Worth the Effort is the strongest standalone title because it's immediately clear what the episode is about. But if you want the title to highlight the contrast between you and Rebekah—which is really the engine of the episode—then: Traveling with Friends: Lessons from a Girls-Trip Regular is a very good compromise. It tells listeners they're getting practical wisdom from someone who actually does this all the time, which is exactly what the episode delivers. Let's do this title" Traveling with Friends: Lessons from a Girls-Trip Regular" now I need a subtitle Here are some subtitle options that fit the actual conversation and complement the title: Best Match How to make girls trips, weekend getaways, and friendship travel actually happen Slightly More Personal What gets in the way—and why it's worth going anyway More Friendship-Focused Why shared experiences deepen friendships and create lasting memories More Practical Schedules, budgets, guilt, and the surprisingly simple path to getting away Rebekah's Philosophy The "worth-it" bar is lower than you think If You Want to Highlight Both Perspectives One friend who travels constantly, one who rarely does, and what we learned More Conversational You don't need Greece, a perfect group, or a week off work Strong SEO Tips for planning successful girls trips, friend vacations, and weekend getaways Very "Dear Nina" What happens when you finally stop saying "we should do that someday" My top three choices are: How to make girls trips, weekend getaways, and friendship travel actually happen What gets in the way—and why it's worth going anyway The "worth-it" bar is lower than you think Given the tone of the episode, I'd probably choose #2. It captures both your perspective and Rebekah's without sounding too instructional. It feels like the subtitle of a conversation rather than a travel guide. Thank you to this week's sponsor: SINCERENOTES. SincereNotes is available to download free on Google Play and App store. Special thank you, as always, to my assistant producer, Rebekah Jacobs!