Nina: Hello, listeners. I am extra excited to be here today ’cause I have my beloved assistant producer, Rebekah Jacobs. Rebekah, you can say hey right away.

Rebekah: Hi, guys. Hi, Nina

Nina: Rebekah and I speak all the time. We text all the time. We voice memo all the time. We talk on the phone all the time, and we have actually formally recorded several times too, and I’ll have those in the show notes. I think our most recent one was we did a full breakdown with our two favorite professors from the podcast Love, Factually of the movie Beaches. Was that the most recent?

Rebekah: I think so

Nina: Oh, it’s such a good one. That’s one of my favorite episodes of 2025. I will definitely replay it again. I just heard that the musical closed. Did you see that?

Rebekah: No, but I’m not surprised based on what we’ve heard

Nina: Reviews were mixed kind of pertinent to today’s topic, which we’ll get to shortly about traveling with friends and girls trips, we did sort of have this concept floating around that maybe we would meet in New York and go see the musical, but I guess we gotta put that one to bed

Rebekah: So sad. I might have to come and just watch the movie with you [00:01:00] though

Nina: So actually, you are coming to town, joining me for the second annual Dear Nina Live, this time in Minneapolis

Rebekah: it would be perfect, not only because of our topic, just because it would be so much fun to come on a girls trip with your friends to Minneapolis

Nina: it’s funny. As I am promoting this show I find myself always saying, “Hey, Twin Cities, I’m gonna be doing a live show in Minneapolis,” and I forget to let people know they certainly are welcome to travel here. I’m happy to give suggestions of where to stay, probably in hindsight I should have made that more a part of the marketing

Rebekah: it’s not too late. We have time, I’m not hardy, so I’m not coming in the winter, but I cannot wait to see it in the summer

Nina: Yes, I forgot to mention Rebekah lives in Maryland, it’s going to be just a fun night out, girls’ night out, Minneapolis is a really beautiful place to come in the summer. It’s an easy place to visit. The place we’re doing it is actually not in Minneapolis the city. It is just outside in a suburb called Excelsior, which is right on Lake [00:02:00] Minnetonka.

It’s a cute little lake town. It really is like you’re somewhere in a little East Coast village-y kind of town, except it’s right in the middle of the country. So maybe it is not too far for some of you to come here. I should mention that the tickets are over half sold. So if it’s something you’re considering, consider it soon

Rebekah: When you were describing it, I was picturing an Emily Henry novel, just picturesque and adorable, and I’m so excited

Nina: It is. It’s just like that. So let’s get to our topic for today, which is traveling with friends, which is something you do all the time, and we are often texting, and you’re like, “Oh, I’m on my way to go on this trip with a friend and this trip with a friend.”

And I have a confession to listeners that you already know, so it’s not a confession to you. it is that I do not travel very often with friends. I was 23 when I got married. We moved to Minnesota right around then. My husband Brian is from here, so this is not my hometown.

My hometown is Chicago. I could probably count on two hands in the 26 years I’ve lived here how many times I’ve traveled with friends, and maybe don’t need all 10 fingers, [00:03:00] I don’t think

Rebekah: Wow. Because you know I’ve gone away probably five times this year, I think we’re great then to bring this topic because somewhere between me and you is probably where many people would find themselves. So I think I’m on a higher end, maybe you’re on a lower end, but I hope by the end of today everyone is convinced it’s worth it to go, and how to make it successful.

there’s a lot of reasons why we can’t go. Why do you think? Do you think it’s guilt? Do you think it’s just life?

Nina: Well, okay, I think we have to mention, finances, which I will not say is the reason that has kept me from going, just to be quite honest, but I think it is a reason, and we need to put that out there, that the financial barrier is something that would keep people from traveling. When I think about what honestly has kept me from traveling more is I have four kids.

I had them each at about two and a half years apart, two to two and a half years, and so each time it seemed like, “Okay, I’m ready to go,” I was maybe either very pregnant it’s not that I didn’t have help, it’s not that my husband wasn’t helpful, it [00:04:00] seemed, like, so insurmountable.

It kind of reminds me of I was an English teacher before I had kids, sometimes even trying to leave town when you’re a teacher and all the lesson plans you had to leave just didn’t feel worth it.

I just remember sometimes, being sick or something, and you’re like, “You know what? It’s not even worth trying to figure out the lesson plans. I’m just gonna go.” I feel like I had a little bit of that sensation about leaving the kids, and then it just kind of became a habit. And there was one other thing, thinking of is that because several of my best friends still live in Chicago, and of course I would go and visit my parents, I would see them, so we didn’t have as much of a need to go away together, but it really would be different if we did.

And then there’s the college friends, which I did travel with. Those are the only people I’ve really traveled with, and we have done it, but not nearly as much as we could’ve. And another one of them has four kids. Another one has three kids. One lives in New York City, Brian and I would go to New York every so often, and I would see her there.

So it’s like we did get to see each other, but she didn’t necessarily need to travel to make that happen. So that’s my [00:05:00] long answer. It feels embarrassing ’cause I talk about friendship so much, and I do think it’s important to visit friends, but I guess I feel like I did see those friends enough, but not in the way you do. It’s different.

Rebekah: It’s true, and I remember one time, when you and I were on the phone, and I think you must have said something, “You’re going away again?” And Mike goes, “See? Even Nina, who writes about friendship, thinks you go away a lot. , he is unique. He is definitely someone who says, “Go, go, go, go, go.”

So I’m lucky in that way. But I’m going hopefully to help our listeners go away even if someone at home is bemoaning the fact that you’re going to leave or even though you have a big work event, I still think it’s worth it, and I hope by the end you think about it in a, in a different way And I think there is that question, right, of who? Who are you going on this trip with? And sometimes it’s very obvious. You have a shared bond. It’s your mahjong group. It’s your book club group. It’s your three college roommates.

It’s your preschool moms. and sometimes it’s one-on-one, and that’s very special, too. It does not have to be a large group to go away [00:06:00] and be worth it. It can be small and intimate. I’ve gone away one-on-one. I’ve gone away with eight people. I don’t think there’s a magic number. Three or four is great. And I know, Nina, we defended on episode 141 our White Lotus triangle. I think three is awesome to go away with

Nina: I like three. Somebody just asked in the Facebook group, again, for everybody that’s a Dear Nina, the group where people ask anonymous questions, and somebody asked about, it wasn’t a trip, it was just a dinner, she was a little concerned that it was gonna be three, and they’re kind of newer friends. when there’s three people, each person doesn’t have to do so much heavy lifting

Rebekah: And it’s interesting, this summer my daughter is going on a teen tour, and they actually require when you go out in town, sometimes you get free time, you must be in a group of three. And I- if you get hurt, you sprain an ankle, someone has to go get help. That’s how they described it. and someone has to be with the friend.

Nina: And I’m really glad you did bring up that it doesn’t have to be a group. Finances are one of the reasons that might keep people from traveling, another reason might be your very first point, who? there is this [00:07:00] image I think people have out there of girls trips.

You can see all the Instagram. You can just see it where it’s like you have to have this perfect group, they don’t have that in their life, and therefore they feel like, ” Well, why would I go on a girls trip? I don’t have a group.” And you don’t need a group

Rebekah: Right. You can do that one-on-one. Gretchen Rubin and her sister go away and they read, and that’s so delightful for them. You have to also, you know, know yourself, Like, I think you and I could do that kind of trip where we would talk, talk, talk, read, you know, go watch some shows, come back.

But you have to know the right person. When I go on a one-on-one trip, I like to have a very, fun-filled agenda. We went to a place where there was sword fighting and Chinese astrology. It was just weird and funky, and that

Nina: Where was this?

Rebekah: like Austin Spa. So it had relaxing, it had fun, but it gave us that one-on-one time, but, but also activities

Nina: right. So you don’t wanna just sit by a pool, but that’s a know yourself kind of situation. I

Rebekah: Yes, ’cause I definitely have friends who just wanna loaf, and literally if I told them, “Let’s go do our Chinese astrology, then do sword fighting,” they would say, “Absolutely not.” [00:08:00] So you have to know who you’re traveling with

Nina: I just read an article, on Jane Pratt’s Substack. Jane is the one who was the editor of Sassy Magazine and was there another one? Oh, I think Jane. Was there one called Jane?

Rebekah: Yeah, there was Jane.

Nina: Yes. Okay, so now she has a Substack, and somebody wrote a guest post about hating girls trips.

Rebekah: my heart just dropped.

Nina: I thought it was important to bring this up, but, uh, I didn’t get the sense that she was with people she was close with. I feel like it was kind of a cobbled-together group, they were somewhere, that had more nature… It was a more nature setting, and she wanted to go on a hike, and somebody else in the group, who she described as the queen bee of the group, wanted to go to an art gallery.

They ended up going to the art gallery, and the entire time she was resentful. And she really did feel like it ruined the vibe of the day. The weather was gorgeous, there was beautiful places to hike, why are we inside this art gallery all pretending to enjoy it? She didn’t feel like anyone enjoyed it. I just thought that was notable

Rebekah: know what’s, what’s interesting in that scenario, and maybe ’cause they weren’t so close, so if I’m going with people who know me forever, I would say, [00:09:00] “You guys go to the gallery, I’m gonna go on a hike.” Or, “Does anyone wanna go on a hike if you’re going to the gallery?” I don’t think there should be an expectation that everyone does the exact same thing at the exact same moment, especially if you’re there for three or four days.

We all have interests at this point. We’re all grown-ups, It’s the joy that I’m not 12 and I have to do what the group does. I don’t think you should be going necessarily to a dinner by yourself if everyone’s going as a group. But if there’s something in the day, I think she also could have said, “You guys, this is my vacation i’m gonna go on this hike. I’m gonna take an Uber. I’ll meet you back at 4:00.” So I think there’s some self-advocacy that you can do to make this trip really fun for you and for everyone, and, and it’s not rude,

Nina: that would’ve been great advice. If she had stopped and asked

Rebekah: she wrote in to Dear Nina, that would be my advice.

And you can also set that up from the beginning. ” We’re going to Arizona. There’s this gorgeous hike I wanna do. Anyone wanna come? If not, no worries.”

Nina: I love

Rebekah: such a

Nina: It’s like being adult about it. We actually aren’t in high school. As it turns out, like you can do your own thing. You are a grown-up. You got yourself there. You probably have a credit card and a [00:10:00] phone, and you can, yeah, meet up with people later. That’s true. You have to be secure enough. This comes up in so many episodes.

You have to be a securely attached person where you can sort of feel, “Okay, I’m gonna be gone for half the day, and that you feel confident that you can slip right back in. Now, if you’re doing a one-on-one trip, I think you guys probably do need to be on the same page for the most part

Rebekah: I agree. I think if it’s a one-on-one, you’ve kind of talked about it, so… And also, I can go to a art gallery. Even if it’s not my jam, you know, I, I could also do that and just maybe we go for an hour or say, my husband makes me go to all these historical houses. It’s fine. Like, I can do the FDR Museum, but maybe not for four hours. maybe for one,

Nina: Well, you and I, you and I always talk about the third way.

Rebekah: The third way.

Nina: third way, and I- that’s a perfect example of okay, fine, let’s go to the art gallery, but just for an hour

Rebekah: So now we’ve decided we’re going away and who’s coming, and now is the least sexy part. You’ve talked about this so many times, it’s scheduling. This is the least fun part, and it [00:11:00] is the most necessary.

If you have on your texts, “Oh, guys, we should go away,” and everyone’s like, “Yeah.” And then they say, “Yeah,” and it stops there, and it’s been two years, it will never happen. So it’s different than saying, “What about May? I know August is busy.” So you have to bring it out. Someone has to do the Doodle poll, someone has to agree to take all of that information, find two or three dates, and then you have to book it

Nina: This is the hardest part. I think it is exactly why I haven’t traveled as much with my college friends, ’cause we try, and we all have good intentions, when we have gone away, it’s because we did nail down a date. That is what it takes

Rebekah: That is what it takes. And one time we actually did the Friday of Thanksgiving, so we all had Thanksgiving with our families, and then we all left ’cause we knew no one would have work. It was just an easier time, ironically, to get away

Nina: That’s interesting, and I don’t think that would work once you guys all have college-age kids because that’s when your kids are home

Rebekah: Exactly. So you have to be flexible. I think with the when, you have to be the bendiest friend. And what I mean by that, [00:12:00] so if you have a friend who’s on a divorce schedule, she trumps my schedule because there’s certain weekends that are harder for her. If you have someone who just had a baby, she has a more challenging schedule than, I do.

I needed grace ’cause I have two older kids and a much younger child, so if I wanted to go away, I couldn’t go away for as long ’cause I was the only one with, like, a baby at home at some point. So when you can be bendy and someone has a more challenging schedule, try to be flexible. It does not mean you’re not busy.

It doesn’t mean you have your own stuff. Of course you do, but any time I could fly to the West Coast, I can.” no problem. I will do that. And I know that some people have a harder time getting on a flight. It’s very stressful for them. That feels less stressful to me. I love the six hours by myself.

I like reading. I like the, you know, catching up by, with no one to bother me and, you know, I watch movies. But I also know not everyone feels that way, and it can be really hard. It’s stressful for someone to get on a plane, , go six hours. so I don’t wanna diminish that it’s a lot.[00:13:00]

But with like a little reframe, maybe you could enjoy those six hours where, you know, no one’s coming in the bathroom with you, and you’re finally, finishing Running Point or whatever you’re doing and, get on the plane, get on the train, and do it. be generous when you can.

Nina: That is just good advice in friendship in general, Rebekah. That requires, a moment of pause. Be the bendy friend when you can. I’m adding the when you can. Like, everybody has times when, you’re right, the divorce schedule is a great example. When the schedule has it that you’re with your kids certain times, you’re not gonna give up those times, and so yeah, maybe the other friends can be more accommodating I think there is an interesting thing to be said about this when somebody is single and doesn’t have kids.

So, you know, not just single but also doesn’t have kids, or married and doesn’t have kids, either way. I can see how there could be resentment. This has come up. We’ve had episodes. We have covered this. there’s resentment that, comes in that direction where they feel like they’re always the bendy friend

Rebekah: Absolutely. if you think of it as a, a straw that sometimes bends and sometimes up, everyone can [00:14:00] be that. So yeah, you don’t wanna always be bending so that you break, but you do wanna be the friend when you can to offer that grace.

Nina: somebody has to, right? You’re never gonna get something scheduled if everybody gets their perfect… especially if you’re talking like seven, eight people. I mean, you’ve done some big trips. I’m, we have to talk about some of these examples, if you’re ready. I mean, I’m gonna let you lead the way

Rebekah: I, I’m ready. Let, yeah, let’s do it

Nina: I can’t tell you how many times, listeners, I have, Rebekah mentioned this already, but we’ve been texting, whatever. I can’t even keep track of her trips, and it doesn’t matter ’cause we communicate on the phone either way. But she’ll be like, “Oh, I’m at the airport,” and we’re going to some far-flung place. And I’m always like, “Mike.” He’s the perfect husband

Rebekah: He’s great. Yeah, no, we did. I went to Utah. We went to Sundance because we have a friend who has a home there, so he was super generous. But I would say here, don’t let Insta mess you up because, of course, would five days in Santorini be amazing? Yes. But would a night in Philly be fun? Yes. [00:15:00] my friend came from New York, I came from Maryland. We literally went to Philly for the night, shared a hotel, got dinner, and went home. if you are dreaming of Canyon Ranch, who’s not a sponsor, but you know, call me. No, just

Nina: always open

Rebekah: We are open for all trip sponsorships. but in all seriousness, go away for one night, even somewhere in your hometown could keep that nourishing friendship fun alive. I was a part of a Navy family, and I told Mike, like, “I will move anywhere with you, but it’s really important that I go see my friends and family.

That has to feel like a part of our lives.” And I would say also, I tell my kids, “I’m going here to go see so and so. I think it’s really important to go see your friends. I hope when you’re g- a grown-up, you go see your friends.” I know a lot of people sometimes feel guilty for leaving their kids. I say, you know, “Love you.

Sorry to miss soccer. I’m going to see my friends. I hope you have that same urge to go see them.” So make sure you’re very honest about it. And also, I would [00:16:00] say think about where you wanna go in the middle. So, um, half my friends are in California, my college friends, and half are in New York, so we always meet in Austin.

We went to college there, so it’s super fun, but it’s also halfway, so we’re kinda all putting in three hours of inconvenience. But I know you also mentioned money. We have stayed, even at this age, we’re almost 50, with our friends’ parents ’cause they have an amazing house in Florida, and it was so fun. We were in bunk beds.

That’s where the grandkids stay, and we were the gr… And it was hilarious, and we were hysterical ’cause it felt like we were in high school. These are my old high school friends, and we loved it. We were in Florida, played tennis, walked around. And also thinking again about being a bendy friend, I have friends who keep Shabbat, and on Saturday, that means you can’t spend money and you’re trying not to be in a car.

And so if you’re at a friend’s house by a pool, it’s great and easy. If you’re at an all-inclusive, you don’t actually have to spend money. So again, thinking about everyone’s needs ahead of time makes that trip super wonderful and super [00:17:00] easy.

Nina: Are you the planner in a lot of these instances?

Rebekah: that’s a great question. It depends on the group. So sometimes I’m like, “I don’t care, I don’t care.” And then sometimes I’m very much type A, holding the passports, leading the charge. But isn’t that funny? I hadn’t really thought about it. I think it’s maybe the role you played in that group at that moment in time.

I don’t know if we all fall back into our roles. I’m usually the one getting the calendar dates and, “Let’s do it, let’s do it,” and helping to pick the place. Once we get there, I usually am fairly laid back, although maybe some people will call in and say, ” that’s a lie,” that I’m n- that I’m never laid back

Nina: It’s true how we play different roles with different friends. that’s a really good point. , It may feel different with the college friends and, it’s funny, we haven’t really talked about couples. I have done more couples traveling or full families traveling actually, uh, more regularly. But I think that’s like not what we’re really talking about here.

Rebekah: and I think it’s different ’cause if you’re there with your kids, I’m still worried, are they… You know, there could be friend [00:18:00] drama when you’re with– Are they hanging out? Did he invite him to play pickleball? And when you’re with your girlfriends, ideally, you are not having those thoughts. You’re letting your hair down.

You’re going on walks. You’re laughing. Uh, we went snowshoeing and ended up in a yurt. I don’t do that at all in my regular life. but it’s, again, don’t let the idea of snowshoeing and ending up in a yurt stop you from going to New York for 24 hours. I am willing to get on a train. It’s four hours. I saw my friend for brunch. We had a sleepover. I came home. And for me, again, it’s reprioritizing the idea worth it.

Sometimes it’s not, quote, worth it to leave to get on the plane ’cause it’s not gonna be long. But that 24 hours is the 24 hours you wouldn’t have had otherwise. And I think of it like a plant. If you don’t see your friends in real life, and if they don’t live near you, you do miss out, and you don’t get to laugh.

And when people come in, we’re busy in our real lives. And so I can talk to you on the phone, but I, inevitably I’m going to get [00:19:00] interrupted by a kid or an obligation, or I have to go, or I’m in the car and you can’t hear me. So when you are together in real life, it, it– You could go on walks. You can laugh a lot, or you can also get really serious. I think we talked about in the White Lotus episode, it was really clear they hadn’t kept in touch, and they really didn’t know who each other had become

Nina: at all

Rebekah: at all. And so it was shocking, and you could tell it was a friendship that was almost on pause or on hold or had screeched to a halt, and they weren’t good friends.

And one wouldn’t even cry until the other two went away. it also allows you to be vulnerable. if you do have a new group of friends, and you do, you know, get brave and say, “Hey, would you guys ever wanna go away?” You know, “I read about a winery an hour away,” it would deepen your friendship

Nina: It really would. So we had Jeff Hall on the show, who is the person who did the study with a group, out of University of Kansas about how many hours it actually takes to deepen a friendship, to make a close friend.

everybody quotes this research. They forget to name where it came from, [00:20:00] so I always do. I sometimes get in the comments of people’s Instagram and be like, “That was Jeff Hall’s research,” a trip would fast-forward that time. If it takes 100 hours to really deepen a friendship, then think about how much time happens even on an overnight. I really appreciate your point about a, a night somewhere is fine.

I’ve actually done an entire episode on that you don’t need as much time as you think you do with your long distance friends. You just need some time.

Rebekah: And I’m similar to you in that when I go to Chicago, I do see my friends who I grew up with, and so it doesn’t feel like we have to then go somewhere. But when we have, it really does deepen it. It gets us out of our own space. And even if you go somewhere 30 minutes away, if we stayed at, someone’s parents have an apartment in the city, or you go to Lake Geneva for the night, it just gives you a different space where you can really I keep saying laugh ’cause I just think you end up in really kind of absurd or funny or just situations where you’re sitting in a bed with a girlfriend. We don’t really get that chance to literally, hang in the bed. And when [00:21:00] I go with certain groups, we do. We share one room. It’s two in a bed.

also, on the reverse, if that sounds horrible to you, you get to say, ” I love you so much. I’m gonna get my own room. At 12 o’clock, I turn into Cinderella, and I am gonna go in my own space, and I’ll see you in the morning.” So you have to, again, really, self-advocate for the trip that you want because it is so special, and it is so hard to get away

Nina: That’s a good transition to those kind of negotiations of are we staying in a house, like an Airbnb? Are we staying at a resort? what one person might consider a vacation, the other person doesn’t. And something that keeps coming to mind, and I don’t wanna forget to say it, no matter where you go, I don’t care what city, I don’t care if you’re in a resort or an Airbnb, all of that, you have to get off your phone. I, I will say, like, I have definitely been on trips, I see it, where if people are on their phone the entire time constantly checking in with stuff at home, constantly on Instagram or whatever,

If you’re gonna go to the trouble of going away and you’re still on your phone the entire time… Like, have you seen that at all?

Rebekah: [00:22:00] Yes. 100% and this is something I had to learn the hard way. the first time I left, I’m sure I left a 20-page manifesto for Mike, you know? Not– A-and he, by the way, knows all of this. It was, ” Henry only likes Smartfood, but Gracie will only eat SkinnyPop.” it was so specific and insane.

And I think if you go, you have to go with your most generous goggles on and not care because they will not do it the way you do it. And I think that is sometimes why people are checking in. And you cannot be aghast if your, kids get served McDonald’s or the sub didn’t do your lesson.

You are the– in the privileged spot of going on vacation, when you come home, everyone will be alive, and that is the goal. So the constant checking in, it adds such a pressure. So give yourself the grace of knowing it’s gonna be okay. Obviously, if there’s a real emergency, check in, but if someone’s not using the blue sippy cup, they’re not gonna remember and, be on the trip

Nina: And it makes everyone else then anxious about what’s happening at home, right? So you see someone else, like, constantly [00:23:00] checking in, you’re kinda like, “Oh, well I guess I should…” Sort of almost out of shame. , “Oh, am I not as good of a mom because I’m not checking in every 30 minutes?”

Rebekah: Correct. I think I was like, “I’m actually gonna leave my phone and I’m not gonna look at it.” Because yes, there is that, wait, if I’m not checking in, am I not being like the good mom? Agree to be there ’cause you don’t get that time back. It is so valuable, we deprioritize fun and togetherness and that nourishment.

Be there, be present. And, uh, another thing that I do, so I wake up very early, and especially if I went to the West Coast. So I wake up early anyways. If I’m on the West Coast, I will be up, it could be 5:00 or 6:00, that time. So I put workout clothes and my workout shoes by the door so that when I wake up, I leave.

Because for some people, they are finally getting to sleep in, and I don’t want to wake them up. I want them to sleep till 10:00 or 11:00. of course, you finally are getting, a glorious night’s sleep. But I do not want to be sitting in the dark by myself trying to, , hide my phone, ‘ then you can bring the phone out ’cause you’re by [00:24:00] yourself.

You know, trying to read my Kindle under the covers. So I bring a book. Whatever I do, again, it goes with knowing yourself and sharing the room. And I’m happy. I go on my walk, I have my coffee. By the time everyone wakes up, I bring them coffee. yeah, there’s a few memes of like a type A, type B friend on travel, you guys should look that up.

Yeah, ’cause again, I’m someone who wants to do a lot of activities. I wanna start early, but I will also let you sleep in to a point, then I’m gonna, I’m gonna wake you up and, make you go to yoga or, or do something

Nina: Listen, people like traveling with you, so you’re obviously doing it right. So other successful trips. So that was, you know, be thoughtful about other people’s, habits of maybe they wanna sleep a little later than you, things like that

Rebekah: Plan your own, I would be resentful if I have to sit in the dark till 11, plan your own trip within the greater good. I mean, people, this, this part might go viral. People have very strong feelings about plane clothes. If you change out of your clothes

Nina: Is that a thing?

Rebekah: It is a thing. Yes, so I ha- yeah, it’s a thing. So some friends [00:25:00] find planes very gross, and they have to shower after and change their clothes. So when I travel with my plane clothes friends, I will always shower and put on new clothes. But certain friends are not plane clothes friend, like they don’t care,

Nina: Okay, I just

Rebekah: then we don’t

Nina: I have never traveled with anybody who cared about that, and I don’t care about it

Rebekah: you might not know. They m- they might have done a secret life.

Nina: Oh, that’s true. Maybe they’re like, “Ew, is she still wearing her plane clothes?”

Rebekah: So again, it’s like know who you travel with or just they also know me, like I’m not gonna wash my hair. I’m gonna come with it already washed. And

Nina: That’s it. That’s it

Rebekah: who’s ever sleeping with me, who’s ever sleeping with me, that is it. Even if we go to a, a honky-tonk, my hair is not getting washed. Which one time we did in, uh, Arizona if we were in Carefree, and that was super fun. And again, something that is not in my usual Maryland life is not cowboy boots, honky-tonk dancing. that was a lot of fun

Nina: Do you feel like on some of these trips, I mean, maybe it’s hard for you to say ’cause these are your actual friends who might be listening, but I’m thinking the bigger groups. So it’s different when it’s obviously one-on-one or even three [00:26:00] people or even four people. Once you get beyond four people, do you feel like there’s pairing off that happens and resentment that happens from that?

These two always are sitting next to each other, or like these two are always kind of looking at each other across the table and sharing a knowing glance, and you’re like, “Oh, are they annoyed with everybody else?”

Rebekah: No, I don’t think people pair off. I think there’s definitely preferences of what people like to do. So I think some people might like to shop and some don’t. I think that it’s more in a large group you get that art gallery hiking conundrum, because once you have seven people, you have more preferences.

I would say it’s more figuring out what you wanna do, having the courage to say, “Ah, that’s not so fun. I’m just gonna go do this,” without breaking up the group dynamics or the harmony of the group

Nina: let’s go back to the bendiest friend one, because I don’t think we’re done with the budget conversation. I can see in certain instances where it makes sense for everyone to take turns bending.

I mean, not just certain instances. In a lot of instances. Budgeting’s a hard one, because if someone truly doesn’t have the money to spend, and it’s… We just did a money episode not that long ago, and [00:27:00] there’s having the money, and there’s deciding you wanna spend the money that way. Either way, it’s not really for anyone else to say, which I think was kind of the conclusion of that episode, is you don’t know what anyone has, you don’t know what they’re saving for, you don’t know what the situation is.

So, whether you think someone should be spending the money or not, they have decided, like, that’s a place they cannot bend. So what happens in that situation?

Rebekah: I think in that situation, you still have a lot of agency. So you can say something like, “I would love to share a room with someone.” Or you could say, “I need to share a room with someone.” Or you could say, “I think that destination looks amazing. It’s out of my price range. What about this?” Or, ” Why don’t you guys come see me and come to my house?”

You can always be a host. It’s different, of course, than necessarily getting away, but I think you have agency. You just have to be honest with your friends. You can also say, “That place looks amazing. I need to save for a year. Can we plan for May 2027, May 2028?” Because now I have a goal, and [00:28:00] so I think if you are honest with your friends, and hopefully your friends are not, offering a month-long cruise.

That just is impossible. So I think there’s, you know, a reality, if hopefully these are people you’re really close with or trying to be closer with. I would say if you know them really well, you m- it might be easier to be direct about finances. It would be easier for me to say that to a friend of 20 years versus a friend who I, I just met.

But it’s still, something that you have the agency to say, “What about this place?” Or, “I can’t really do that, but you guys go ahead.” I mean, that’s another thing, and we didn’t actually talk about that. That’s also a way of being a bendy friend. When you get that schedule together and six people can make a date but one can’t,

Nina: Oh.

Rebekah: this is tricky, but I would say the six people should go because it might be a whole nother year, and if I was the seventh friend who couldn’t make it, I would hate for everyone to miss out on this chance, on this fun, just because I can’t make it work.

So I would truly say, “You guys should definitely go.” I would not be saying it hoping they actually don’t go. I would really mean it, I will come next [00:29:00] year because I don’t want to stop that. But I think that’s hard to do

Nina: That takes a real grown-up, which I think is great, and I think everyone should aspire to that actually. I really do. I’m gonna say something demonstrative here. I don’t always. That is the goal, I hope more people will get there and think about getting there. You have to work on your security if you’re gonna do that.

You have to be secure enough to say there’s gonna be a couple inside jokes from this trip, that’s just how it is, that I’m not gonna know. There’s gonna be some side group text stuff that they don’t wanna bother me with, you have to be secure that you’re gonna still be on the other group text that isn’t about the travel anymore, because you don’t need to be on the text for that trip.

Rebekah: And we had that happen where we all were able to get to New York. Our schedules are so tight, one person couldn’t do it, and she said, “Guys, go.” and we did so it does take a lot of generosity of spirit.

you never actually know about next year. I have pictures from my mother-in-law, who passed away in her 40s, and she went on a trip to Paris with her best friend, and the best friend recently sent me those [00:30:00] pictures. And it’s so special, and they are hysterical. They’re, like, with a waiter.

I don’t know the story. I’ll never know the story, but you can tell it was funny, and they’re holding up a water bottle. And, uh, those pictures are framed next to my room becau- in, in my bedroom because it was so special. And they did get away, and that was, I don’t know, 1970-something. And it must be easier to, to travel now,

Nina: right. Exactly.

That’s

Rebekah: and my computer and

Nina: That really is a good point, and it’s kind of like the unsaid, and we now said it. But it’s, we didn’t really spend a lot of time, ’cause I don’t think it’s necessary, about why you should even bother with all this in the first place. And it’s, it’s like creating memories, it’s deepening the friendship.

if you’re starting to become somewhat closer with people even in town and trying to take it to another level, because you’re not gonna do a random last-minute out-of-town trip with long-distance people. How do you even know them? I, I guess that, that’s totally true. I have my friend Pam Moore, who’s been on the show several times, lives in Boulder, and I [00:31:00] went out there with my college friends, but then I stayed longer to be with her.

So that was one of those rare things to deepen a out-of-town friendship where we really were only long-distance friends. But, all of this stuff, we do all these things because friendship matters. the reason I said it’s unsaid, unspoken, that’s the whole thesis of this entire, not just episode, the entire show.

when people pitch us and they’re like, “Friendship’s important,” I’m like, “Nope, that’s not the episode,” ’cause that’s every episode

Rebekah: And if you think about how we started, about how it sounded so hard, you had your four kids, we feel guilty, all the things that stop us, we get into a routine. I come back energized and refreshed. I think I’m a better mom. I think I’m a better wife because I had that moment where I don’t have to have those roles, which I cherish but I get to be more Rebekah without that, uh, role of mom and wife. It’s a different me that gets to have that weekend, and then I come home and I’m ready to sit on the soccer sideline. I’m ready… Well, I don’t really make dinner like you do. I’m ready to nuke those

Nina: that’s why you can go away and I can’t. I’m like, [00:32:00] I’m too central in the dinner role here

Rebekah: you know what, ladies? Yeah, to everyone, may this be the takeaway. If you are terrible at making dinner, no one notices when you leave. And so, yes. So that’s how you can have your girl trip. So it all comes down to that. Who knew? We, we have a new thesis,

Nina: uncovered the mystery. Mike can order food too.

Rebekah: yeah. Go burn your dinner and by next month you too will be, uh, at a honky tonk,

Nina: I was just thinking about something. Brian’s so strict. he’s just a strict person. And so when I would go away here and there, the kids would be like, ” You can never leave.”

Rebekah: Mom, come on. I think we did the who, someone that you have a natural kind of bond with or someone you’re trying to deepen. When, get that unsexy calendar part, make that Doodle poll, and make it happen. And then respond. When someone texts and you finally have the date, don’t be the person that takes two weeks to respond.

We are all waiting for you. And where, don’t let [00:33:00] Instagram talk you out of one night in Philly, one night anywhere. it doesn’t have to be Greece to be great, and you can meet someone for 24 hours. It is still worth it. The worth it bar is lower than you think.

And the why, we chronically deprioritize fun, and this is permission to have some fun, not get interrupted, remember who you are outside of your role at home. kids won’t remember if they’re young, I promise.

And your older kids, I want to remember. I want them to know, and I tell them very deliberately. And finally, make it work. Be honest about your budget. Help out with the time zone. Be the bendy friend, and if, uh, someone at home is having Mickey D’s, do not check and tell them that it should’ve been organic I don’t know, Nina, I don’t cook organic soufflé.

Nina: Souffle. No one’s made a souffle in this century. Oh, that’s so funny. Rebekah, this was so great. First of all, you’re such the perfect guest. You’re so prepared. You’re, ’cause obviously you’re the assistant producer of this show. I love how you [00:34:00] wrapped it up at the end.

Rebekah: Well, hopefully people loved it ’cause you had such good follow-up questions. You have such an interesting way of making the conversation turn in a way I didn’t think about, and then I have to be on my toes. So I love it, and I hope we bring that same fun energy to our night on July 29th

Nina: and it won’t be recorded, so that’s the final note I want people to know. That we, we did record the Chicago one, and I’ll put that in the show notes ’cause that’s a really fun episode about friend groups and exclusion and we answered some really difficult letters, but this one we decided is not going to be recorded. you really have to show up

Rebekah: Can’t wait. We hope to see you there

Nina: All right, listeners, come back for an episode next week when our friendships are going well. We are happier all around. Find us on Instagram at dearninafriendship, TikTok, and the newsletter is at dearnina.substack.com

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