The Art of Group Adventure Diplomacy
Outside's love guide answers your most pressing questions about dating, breakups, and everything in between. Today, we discuss how to make sure everyone has fun—from stoner to straightlaced, slow to speedy, risk-averse to reckless.

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Welcome to Tough Love. Every other week, we’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsidemag.com.
Q: This guy I’m dating always wants to get stoned when we’re camping, and to me that’s kind of the opposite of the point. He says I’m being no fun when I ask him not to. How can we compromise?
—Weed-Free
Q: How do you deal with differences in adventurousness and risk aversion when you’re doing outdoor activities with others? I observed a friend and her partner when we did a New Year’s hike a couple years ago—my friend wanted to climb to the icy peak, while her partner was uncomfortable and nervous about the conditions. My friend went ahead without her, and her partner stayed behind and felt left out.
—Cautious
Q: My boyfriend and I have been hiking and camping together for years, and we love it! There’s one thing that always seems to dampen the experience though: He is just much faster than I am. It’s not that I’m terribly slow (I go on solo hikes regularly), but he’s just taller and stronger than I am in general. Occasionally, on a steep uphill, I need to take a break, and I can tell he tries to be understanding, but I know he just wants to keep moving. I’ve told him to go on ahead and that I’ll catch up, but he refuses because he doesn’t want me to be alone. What can we do to help this situation?
—Slowpoke
Earlier this summer, some friends and I went backpacking on Lake Superior’s Isle Royale. Our group included an artist who was five months pregnant (who also happens to be a marathon runner), someone recovering from foot surgery, a taxidermist with lots of backwoods experience and a new fascination with ultralight camping, a woman who had never backpacked before and didn’t realize that was the plan until the day we left, and my husband and me. Personally, I wanted a straight-up vacation—as a semipro dogsledder, I use the off-season for work and rest. My husband wanted quality time with friends he didn’t see often. Our co-backpackers wanted, in no particular order, to log 20-plus miles a day, to take it easy, to see moose, to watch birds, to climb every peak on the island, to relax with their journals, and to gorge on wild strawberries (that was me again). The trip was a blast, but it took some negotiation to get there. We had to sit down, be straight with each other, and think pretty creatively.
Under some circumstances—say, going to a restaurant—we understand that people won’t all want the same thing. But for some reason, with camping, there’s often a unique expectation of agreement. I mention this because the core challenge to our Isle Royale trip is the same as all three of these readers’ questions: What do you do when people have different expectations for the outdoors, and those expectations don’t line up?
Nobody should feel bad if they don’t want to climb an icy mountain. But it’s also frustrating to be held back, and with a couple, the pressure is on both people to stick together the whole time. One solution is to travel with more people. In a bigger group, you can have your stoners and your straight-edge folks, your speed walkers and your amblers, and nobody goes without company.
The core challenge to our Isle Royale trip is the same as all three of these questions: What do you do when people have different expectations for the outdoors, and those expectations don’t line up?
You should discuss, ahead of time, what everyone envisions for the trip. You already negotiate who’s bringing the water filter and who’s carrying the stove; it’s just as easy to be proactive about activity preferences. Make sure that in addition to sharing what you all want, you should also say what you don’t want. For some people, it’s frightening to be left alone or to walk after dark, and making that known to the group can ease a lot of anxiety. Others will be actively disappointed if they don’t get solo time, or they may be cautious of committing to an itinerary because of physical constraints. You may be surprised by how little you can predict these things.
Weed-Free: What is the point of camping for you? Is the problem that your boyfriend’s smoking at all, or that pot affects his personality, or that he’s self-medicating for something else entirely? This may represent a deep conflict in philosophy about substance use, but it could also be as simple as the fact that you want to go fishing and your guy likes to nap when he smokes, which makes for a workable compromise.
Slowpoke: Since you go solo hiking regularly, is it possible that your boyfriend is the one who doesn’t want to be alone but is afraid to admit that? You could even your pace by giving him some of your pack weight, which would speed you up and slow him down. Or, if his goal is exercise, he can do sets of push-ups while you catch up. He also might just value hiking as a way to spend time together and doesn’t want to feel like he’s ditching you. Maybe he’d feel better if you sent him ahead with a task, like pitching camp or boiling water for dinner.
Cautious: The best way for partners to deal with risk preferences is to give each other space—let the bolder partner climb as many mountains as she wants!—but make sure not to ditch each other when you’d planned to be together. There’s a time for adrenaline. There’s a time for companionship. And it’s up to every couple to determine how much those times overlap.
Your turn—ask away at toughlove@outsidemag.com.