The Case for Doing Things Alone

Let me tell you about the best trip I've ever taken.

I went on a gay cruise by myself. No friends, no partner, no social safety net. Just me, my suitcase, and a wardrobe that was significantly more revealing than anything I'd have packed if someone else was watching.

It was incredible.

I talked to everyone. I dressed the way I actually wanted to dress. I visited the Red Light District on the ship every single night. I had more hookups than I've ever had on any trip where I went with people I already knew. I felt more confident, more myself, and more alive than I had in years.

And here's the thing — none of that would have happened if I'd gone with friends. 

That's because 2 things would happen: First: I'd defer to doing whatever the group wanted to do, and miss out on doing the things I'd really like to be doing. Maybe I wanted to find an empty sling and stop for an hour or so, but the group wants to go to a show in the theater. I'd always defer to what others wanted to do. Second: Because my friends are there, my shyness and shame would kick in because these people who are super close to me, people I've known for a long time, have an already developed idea of who JD is. It's great when people know you, but sometimes that familiarity can feel like shackles. How do you evolve yourself when the weight of those expectations weigh you down?

Why going alone is actually the power move

Most guys don't go to bear events alone because they're afraid. Not afraid of the event itself, but afraid of what it says about them. If I go alone, people will think I have no friends. If I go alone, I won't know what to do. If I go alone, I'll just stand in the corner watching everyone else have fun. If I go alone, I'll spend the entire event alone.

Sound familiar?

Going to events that are usually frequented by friend groups can seem counterintuitive, but it's actually a really great idea and here's why:

When you show up to bear events with friends, you bring everything with you — the social dynamics, the in-jokes, the version of yourself that everyone in your group already expects. You spend the weekend being the person they already think you are. And if that person is shy, or reserved, or not quite living as openly as you'd like — well, that's who you'll be all weekend too.

Going alone strips all of that away. There's no one to retreat to when things feel awkward. No one whose opinion of you is at stake. No social crutch. Just you, and whoever you decide to be this weekend.

And because you have no one to talk to, you'll talk to strangers. Because you have no plans, you'll say yes to things. Because no one is watching, you'll dress the way you actually want to dress. Because there are no expectations, you'll meet them all.

Bear events are also a safe place to explore

Here's something else nobody talks about openly. Bear events are one of the few places where you can explore kinks and fetishes in a judgment-free environment. Pup play, leather, singlets, Dom/Sub dynamics — all of it exists at bear events, openly and without apology.

And here's where going alone becomes even more valuable. If you've ever been curious about any of that but kept it quiet because of what your friends or partner might think — going alone gives you the freedom to explore without an audience. Nobody from your regular life is watching. Nobody has a predetermined idea of who you are or what you're into.

Want to try on a leather harness for the first time? Do it. Curious about pup play? Go find the pups. Interested in what a Dom/Sub dynamic actually feels like in practice? Bear events are where you find out.

You don't have to commit to anything. You don't have to label yourself. You just have to be willing to be curious. And that's a whole lot easier when you're not worried about what your day to day friend group thinks. Getting more confident in a fetish or kink and finding like-minded people can help you get the courage to come out all over again, this time out of the kink closet.

The three fears — and why none of them are real

"I won't know what to do."
Nobody does on the first day. Strike up a conversation with someone and tell them it's your first time. I promise you, nine times out of ten, that person will immediately want to help you have a great experience. Bear communities are warm. Vulnerability is disarming. Honesty gets you further than pretending you know what you're doing.

"People will think I'm a loser for being alone."
Nobody is thinking about you as much as you think they are. Everyone at a bear event is focused on their own experience. And the guys who notice you're alone? They're probably relieved someone else is too. Be the person who makes the first move.

"The fun is for other people, not me."
This is the big one. The belief that bear events — pool parties, theme nights, all of it — are designed for a certain kind of bear. The popular one. The confident one. The one who already belongs.

That belief is wrong. Bear events exist specifically because there are men who spent years feeling like the fun wasn't for them. The whole point is that it is. But you have to decide to participate. Nobody is going to come find you and drag you onto the dance floor. You have to get up and go.

Start smaller if you need to

Going to a bear event alone feels like a big leap? Start smaller. Go to a movie by yourself. Eat at a restaurant alone — actually sit at a table, not the bar, not takeout. Take a day trip somewhere you've never been without telling anyone where you're going.

Every time you do something alone, you build a little more evidence that you can handle it. That you're actually good company. That you don't need someone else's presence to justify taking up space in the world.

By the time you walk into your first bear event solo, it'll feel less like a leap and more like the next logical step.

Go. By yourself. This year.

I didn't expect to enjoy a solo cruise as much as I did. All of this self-discovery and giving myself permission to explore "me" was unexpected, but wonderful. It showed me that I can be the fun, outgoing person who strikes up conversations in line, or at the pool, or on an outing. I was able to customize my schedule to the things I genuinely wanted to experience. Now, when I go on my next cruise or to a bear event with friends, I know that I can be that person and not look/feel awkward. It was such a transformative experience that when I got home, I immediately told all my friends about the great time I had and all the ways I opened up and did new things out of my comfort zone. And they were all really happy for me. I knew they would be, but I still am glad I did the cruise solo ,for me and for the person I'm working towards being.

I'm not saying every event needs to be a solo adventure. But if you've never done it, do it once. You might be surprised by the person you find when nobody's watching.

Drop a comment if you've had a similar experience or if you have questions or comments.

— JD Bear 🐻
Built to Show Off.