How do I talk to a friend of just over a year about concerns I have over our upcoming two-month backpacking trip?

For context, we're all 21-year-old women. The group is me (Abby), Lynn, Talia, and Gwen (all fake names).

I've been close friends with Lynn and Talia for about five years, and Gwen joined our friend group a little over a year ago.

She fit in almost immediately. She's one of those people where it felt less like getting to know someone and more like catching up with someone I'd known forever. Soulmate level. Lynn, Talia, and I all live within about 15 minutes of each other, while Gwen and her boyfriend live an hour away.

When I met Gwen, she had recently ended a two-year relationship. Not long after, she briefly went out with a complete loser who stood her up on their third date before she met her current boyfriend. They just celebrated their one year anniversary.

When they first started dating, Gwen would tell us stories about him like they were silly stupid quirks. She'd laugh about things like him intentionally smashing glasses or peeing all over public bathroom stalls when he was drunk (he even showed her videos), but she'd always follow it with, "He doesn't do that anymore," or, "I told him he shouldn't do that."

About 3 weeks into dating, she kept mentioning that they'd had "a talk." I always thought that was really weird because they barely knew each other. Then, around 2-3 months into the relationship, we asked how things were going over dinner, and her response was simply: "It's fine. He's fine."

My family had recently watched Ted Lasso, so I quoted Roy Kent's speech about not settling for "fine," especially when you're only 21. She seemed to consider this but nothing changed.

A few months later, during the winter, the 4 of us planned a girls night at my house.

I got off work first. Gwen had the day off and was running errands in the city before coming over. Talia also had the day off but was busy beforehand, while Lynn was working later.

This day was around -40°C. Gwen called me saying her car battery had died at the liquor store which was about 45 minutes away and her phone only had 2% battery left. 

I told her to go back inside the store and ask if someone could boost her while I figured out how I could come help, I don’t trust my car to boost someone else's in that kind of weather. So I was trying to see if I could take Talia’s or my moms car. Thankfully, someone inside gave her a boost, and she made it safely to my house.

After putting her car on a battery charger, we waited for Talia so we could grab sushi. While waiting, Gwen disappeared into the bathroom and was clearly talking to someone on the phone. I asked who she was talking to. It was her boyfriend.

After Talia arrived, we went to pick up sushi, stopped at the dispensary, and then went to the grocery store for snacks.

When we got to the grocery store it was around 8 p.m., Gwen asked Talia to leave the car running because her boyfriend wanted to call her.

Talia and I were confused because she could have simply called him while walking through the store with us. Talia and I were in the store for 15–20 minutes. When we came back, Talia jokingly asked, "What was that about? Did you guys break up?" Gwen replied, "No. He was upset that I called Abby first instead of him when my car died."

That really stuck with me. To me, it seemed incredibly immature to be upset that your girlfriend called the friend who was hosting everyone and expecting her for help. It gave me crazy second hand ick.

He also called again later that evening.

About a month ago, Gwen, Talia, my parents, and I went on a short road trip together.

Talia had to work during the day, so she met us later that evening. My parents spent the night with their friends while the 3 of us went out to eat together.

Talia and Gwen drank throughout dinner. So I assumed the position of DD. I drove us to meet my parents and their friends to go bowling where they continued to drink. I actually prefer to be the DD instead of organizing a ride or getting an uber. We went to another bar with my parents after bowling. Gwen and Talia were literally whispering in my ear that I should drink and trying to feed me their drinks. Twist my arm I guess.

My mom offered to drive us back to the hotel, so I started drinking too. We got an Uber from the hotel and ended up going out to 2 bars that night, we stayed at the last bar until close.

Important detail: Gwen's phone was the only one with data, so she was the only person who could order an Uber and access maps.

When we left the bar, the Uber wait was about a 45min wait. I suggested we start walking and order one on our walk. Instead, we spent nearly two hours wandering because Gwen repeatedly refused to order an Uber despite Talia telling her we can order an Uber several times. I also asked several times to look at the maps because it didn’t make sense the way we were going but Gwen would not show me.

During the walk, Gwen kept falling behind. Talia went to check on her but realized that she was talking to her boyfriend on the phone. So she left them alone. At the time, I didn't even realize she was on the phone.

Talia and I were singing and walking/skipping arm in arm. We would stop to make sure Gwen wasn’t getting too far behind. Eventually, she became upset and said we'd abandoned her. In hindsight, I handled that badly. I'm a loud drunk, and one of my biggest pet peeves is when someone excludes themselves from the group and then gets upset about it. I ended up yelling something like, "Then walk in front!"

Talia stepped in, calmed things down, and eventually we all finished the walk together singing arm in arm.

The next morning, none of us talked about it.
As we drove Gwen home, something else happened that felt odd to me. As soon as we entered Gwen’s town, her boyfriend pulled out from a side street, followed us all the way to her house, waved at us without saying hello, and walked her inside.

Later that day, Gwen texted us apologizing for being "grumpy."

We accepted the apology, but I still felt like the situation had never really been properly addressed. It felt unresolved.

Back in January this year, before the road trip and dead car, Lynn, Talia, and I started talking about doing a two-month backpacking trip abroad.

Early on, I invited Gwen, she's a full-time student while the rest of us work and study part-time, she wasn't sure if she'd be able to come.

Over the past several months we've had multiple planning meetings.

A couple of weeks ago, she finally confirmed that she was coming! We were all excited.

Then Lynn asked whether she'd talked to her boyfriend about it.

Gwen said she had, and that while he told her he was happy for her, he was also jealous and worried that Talia, Lynn, and I would encourage her to cheat on him because his ex had kissed someone in a club because her friends apparently told her to.

I found that extremely insulting.

Not only does he apparently think Gwen would cheat on him, but he also assumes her friends would pressure her into doing it.

I asked Gwen, "If he told you he didn't want you to go, would you stay home?" She answered, "Yeah."

That honestly shocked me. Giving up a once-in-a-lifetime two-month trip because your boyfriend doesn't approve feels like a huge red flag to me.

She also said she and her boyfriend had concerns about our safety on the trip because of what happened on the road trip. She told us that he "wasn't impressed" with how Talia and I handled that night because remember he was on the phone the whole time, just listening to our argument.

She suggested we always have a designated sober person while travelling and buy drink covers.

Neither of those ideas would have bothered me in hindsight, in fact, as we know I usually am the designated sober person, and I'm completely happy to continue doing that.

The trip we are planning is a backpacking trip, this means staying in hostels and camping for the majority, personally I do not want to spend all my trip money on alcohol and all my time nursing hangovers. Also where we are going is so much safer than our city and downtown.

I'm starting to worry that if Gwen gets upset during the trip, she'll immediately call her boyfriend instead of talking to us directly. I'm also concerned about how much influence he seems to have over decisions that affect all four of us.

Also she seems extra distant and is showing no effort to make any plans with us.

This is the first real tension we've had as friends, and I don't want it to become a bigger issue while we're overseas together.

We're having another trip-planning meeting this week, and I'd like to talk about communication, specifically in the instance that someone has an issue during the trip, we can talk to each other first instead of involving someone who isn't there.

How can we have a productive conversation without making Gwen feel attacked?