Welcome to Tough Love. We’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Small Game and Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsideinc.com.

　　I am an amateur outdoorsperson, and recently got really obsessed with a new activity. For the sake of this question, I’ll say it’s climbing. It’s something I thought about doing for a long time, but never had the guts, and didn’t think it was quite right for me, as I didn’t start young enough and have the “wrong” body type; you know, all the things we tell ourselves because we’re scared of following our dreams. When I finally took the leap and tried climbing myself, it was like an epiphany. This is what I am meant to be doing right now. I love doing it, and it brings me excitement everyday. I even moved somewhere that’s a hotbed of climbing so I could be closer to the community.

　　For my day job, I work at a coffee shop. One of our regular guests is a very accomplished climber. Not quite a household name, but very respected and well-known in the sport. If he were ever open to mentoring me, it would be a dream come true. I want to talk to him, but my friend said it would be weird to approach him. Is there a way to try to build a connection that isn’t too pushy or awkward?

　　When I was 19, I went to Alaska for a mushing job. My coworkers and I were hanging out on a beach near Juneau when a woman walked by with about ten loose huskies swarming around her. She waved, we waved, and then she and her dogs continued on their way.

　　“That was Libby Riddles,” whispered my coworker.

　　Libby Riddles? The first woman to win the Iditarod?!

　　I turned around, looking for her, but she was already gone.

　　The rest of the season was full of moments like that: casual encounters with mushing icons, people I would have been too tongue-tied to speak with, except that they were my colleagues and neighbors and boss. I tried to be cool (I was not) and eventually I got used to it (kind of). Now I call some of those icons my friends, and we have normal relationships, except for when I occasionally get flustered by remembering how incredibly talented they are.

　　If you moved somewhere for climbing—and climbing heroes are randomly showing up at your coffee shop—then odds are good that you’ve ended up somewhere with a real scene. The place to be. Way to go! It’s certainly possible to be involved with something on your own, in isolation, but there’s something incredibly special about being at the hub of the activity you love: the place where its culture is happening, and being made, all around you. Even if you’re not there forever, it’s super exciting that you made the commitment and journey to be there now.

　　Which brings us to your coffee shop dilemma. I think it’s totally fine to show your hand, so to speak, and tell your hero that you recognize and admire him. In fact, that might make things less awkward; there’s a good chance that he’s already noticed you watching him, and figured something’s up. But I’d keep the interaction short and polite: “Hey, you’re Alex Honnold, right? Amazing, man. Your free solo of El Cap completely inspired me. Did you want cream in your Americano?” “Inspired” is a great word for you to use, because if he wants to deepen the conversation, or is feeling generally chatty, then it sets the stage for him to say, “Nice! Are you a climber yourself?” But if he’s in a rush, or cranky, or an introvert, he can smile politely and go about his way.

　　But wait, that’s it? What about asking him to be your mentor?

　　If he seems into chatting for a while—and it feels natural to bring it up—then you could mention that you’re new in the area, and have been looking to get more involved in the community. Or you could go ahead and ask a specific question you’ve been wondering about, like if you’re choosing between two brands of equipment, and wonder which he prefers. But mentorship is a big deal, and I think bringing it up early is a surefire way to seem overeager and maybe even disrespectful. It’s kind of like if you spotted someone across a bar and thought, gee, I’d like to be in a long-term relationship with them. You might think you want that, but so much is dependent on chemistry, and you’ll definitely scare them away if you ask for too much too quickly. First you have to go on a date. And if that goes well, more dates. And before that, you might start with a simple conversation. At any point in the process, you’re likely to discover that they’re not who you imagined them to be at first glance.

　　That’s true of your hero, too. It kind of sounds like you like him because he’s famous, and you want him to be your mentor because, well, who wouldn’t? But the thing is, you don’t know him at all. You only know who you think he is: the guy who’s too good to be true, the perfect, dedicated, available mentor that you’re craving. For your hero, there might be something aversive or even sad in a relationship like this, were it to proceed. He knows that a fan getting to know him in person might mean a series of disappointments as they discover that he is not, in fact, the person they’ve built him up in their mind to be, but rather an anxious workaholic with a messy car and a habit of responding to texts way too late. Or something. You get the gist.

　　In fact, if you are ever going to be friends, and if the chemistry happens to be just right, it will probably happen organically and slowly. And it will probably be because you run into each other repeatedly in the climbing scene, and not because you hit him up before his morning coffee. So by all means, say hi and be friendly. But you’ll probably have better luck in your social goals by getting more involved in your sport’s community.

　　And as you do get more involved, a funny thing might happen. You might find out that your actual perfect mentor is someone you never expected. Or you might find out that you don’t need a mentor to progress; you just need friends who care.

　　Your hero at the coffee shop is the icon of right now, or maybe of yesterday. He’s a generation or two ahead of you. But your generation in the sport—the athletes coming up right now—will have its own icons, its own heroes. They’re not famous yet, but they will be. They’ll do things that the current heroes can’t even imagine: break records, break paradigms, things that haven’t even been thought of. They might be the tall woman at the gym, or the other rookie you befriend at the competition: the friends you make now and hold onto forever. They might even be you.