Welcome to Tough Love. Every other week, we鈥檙e answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of . Have a question of your own? Write to us at toughlove@outsidemag.com.
This guy and I became fast friends in the last month of our senior year of college. We had instant chemistry, we read each other鈥檚 thoughts, and we really love being outside. He鈥檚 one of the few feminist hetero guys I know. Basically, a total dreamboat. But we were headed in totally different places after graduation. It felt like we were two ships passing in the night.
Our whole friendship is full of sort of鈥 signs. I was feeling witchy and looked up our astrological compatibility, genuinely hoping it would help me get past this, and it told me that we鈥檙e a perfect match. We were both accepted into the same graduate program, but only one of us attended. One time we were on our way to the same concert (not even knowing we were in the same city), and I had a feeling and opened my phone to ask him where he was, and he texted me: You going?聽Another time, I was talking to a mutual friend,聽who is closer to both of us than we are to each other, about how well we get along, and he started laughing because this guy had literally said the same thing to him the day before.
In the five years since college, we鈥檝e been away on separate nomadic adventures. We check in on each other on Instagram, but both of us are so frequently out of service range that we haven鈥檛 kept up a regular correspondence. I only see him once or twice a year, but every time we hang out, it鈥檚 like no time has passed. I feel like we鈥檙e connected in this weird way. I can鈥檛 seem to shake the thought of him, and I鈥檓 worried it鈥檚 creating a cloud of unresolved energy hanging over me. Long story short, I think I鈥檝e found my dream guy, but he lives really far away. What should I be doing?
I鈥檝e been resentful of omens ever since a guy dumped me because of a dream he had about cinnamon rolls, which were, apparently, a metaphor for me. So I鈥檓 probably not the person to ask about signs. But I think these sort of things are very good at helping us identify and trust what we already know and feel (in other words, cinnamon-roll guy wasn鈥檛 that into me). You like this person a lot. He seems to like you a lot. This liking-a-lot thing has lasted half a decade. That means something, my friend. At the very least, it means that this connection is worth exploring so you can know whether to let go of it or not.
It鈥檚 time to gather your courage and write another letter鈥攖his time, to him. Tell him what you told me: That you admire him, that you鈥檝e cared about him since college, and that you still think of him often. That you鈥檙e attracted to him. That you wish you聽had a chance to see where your friendship might lead.
Then send the letter. It鈥檚 scary, but you can do it. Because no matter what he says, you鈥檒l still be in a better place than you are right now.
Let鈥檚 tackle the worst-case scenario first. Maybe he doesn鈥檛 feel the same way, or he鈥檚 in love with someone else, or he鈥檚 super attached to being single right now. That鈥檚 fine, if disappointing, because it gives you clarity: it鈥檚 time to move on. It might seem daunting to find someone who fits the same qualifications, but keep in mind that there are plenty of outdoorsy, feminist聽straight guys in the world鈥攅ven if it doesn鈥檛 always feel like it. They might be at the checkout stand of the food co-op聽or in your hiking group聽or on an online dating site. You might even already know them, and as you work to move on from your long-distance crush, you鈥檒l be far more likely to make space for them in your life.
Of course, there鈥檚 another option, one that鈥檚 exciting and long awaited and possibly even scarier: Maybe he feels the same way. Maybe he, too, wants to know where your friendship could go. Maybe鈥攖his time around鈥攜our lives are no longer headed in incompatible directions.
If all of these are true, it鈥檚 time to buy a plane ticket. Not for the kind of incidental hanging out you鈥檝e been doing occasionally, but for a real extended date, a few days during which you can take long walks and talk about your goals and dreams and eat ice cream and basically see if the聽intense chemistry is still there, if your connection feels enduring and worth pursuing. If things are right聽when you鈥檙e together, the signs will be there. It鈥檚 time for you to let them happen.