How to Have Fun in a New City Solo

Traveling always seems fun. And when we picture ourselves traveling or moving to a new place on our own, we play it out in our heads like a scene from Eat, Pray, Love — wandering around a new city with the sun in our hair, riding a blue bike gracefully across a bridge overlooking a waterway lined with brightly-colored buildings, laughing and eating all kinds of pastries without gaining weight. You get it.

And while roaming around a new city can be as rewarding as what we see in the romcoms on Lifetime, it can also be hella uncomfortable. Going to a 4-star restaurant that has a cult following on IG feels pretty glamorous until you make your way to the booth side of your two-seater table and realize the amount of effort it takes to not let your ass, gliding over the brim of the table alongside yours, interrupt the v cute couple sharing dessert (who may or may not be noticing the small moth hole in your yoga pants at this point). And if you don’t feel awkward enough from the ass->arm contact that you just made with your new neighbor on the right, the pity smile and joke you don’t quite hear from the woman sitting 14 inches to your left will definitely do it.

But while these moments definitely exist, there are plenty more experiences that are so unexpected and exciting that you start feeling a new kind of thrill and confidence that you might not have felt before. Traveling by yourself to new places ignites a feeling of fierce independence that you can’t get from other situations. But to get there, you have to be ready and equipped to handle the discomfort.

After traveling for months at a time on my own in both San Francisco and Sydney for work, I’ve felt both complete exhaustion and isolation as well as the-world-is-my-runway-level confidence. But the things I decided to do (or not do) solo completely defined my overall experience in those places; my memories and associations from each trip couldn’t be more different.

So after learning from my mistakes, listening to Beyonce’s “Me, Myself & I” on repeat, and living with legit FOMO and some serious feelings of lost time, I’ve outlined how to make the most out of traveling by yourself. These mantras have helped me build the confidence I want but never seem to have enough of and helped me push my hesitation and discomfort aside to actually live out the moving pictures I have in my head.

1. You gotta accept it.

   Now, not to get too scientific on you, but let’s assume each experience has a max fun level, and experiences are measured on one of those High Striker carnival games where you try to hit some metal plate with a hammer and some other metal ball shoots up vertically toward a bell but falls just short of ringing it. The objective though is to hit said plate so hard that metal ball has enough momentum to reach the bell.

   So let’s pretend the bell is essentially the max amount of fun you can have when traveling. And if you’re like me, you’re probably thinking Max Fun Level is only achieved by going with someone else, so okay — let’s go with that.

   Let’s say max fun level is 10; your bell is at 10 and no matter how much stronger you get, you can’t go beyond that. So let’s assume that to ring the bell that’s at level 10 you have to have a combination of good company and a fun activity.

   So here we are, realizing that because we are solo, we might not be able to hit the max fun level and ring the bell. But how many times do you play high striker and think “I don’t even want to play this if I can’t ring the bell?” Answer: never. You play because you want to see how high you can get AKA how much fun you can have. If you have the former mentality, you are always going to be let down because you are betting against reality and certain circumstances — it is physically impossible to do something with your best friend and travel buddy you’ve known since middle school if you are traveling solo for work or if you moved to a new city where you don’t know anyone. So even if that is the ideal situation, it isn’t going to happen, and that is certain. So if you keep opting out of experiences due to the fact that said experience would be more fun with someone else, you will always be left with one option: to do nothing. And that’s because you are betting against your circumstance, and that is something you can’t change.

   So to win, even if you know you won’t be able to ring the bell, you have to at least try, right? So yes, while some experiences might not hit max fun level, they’ll ring a solid 8.87 and 8 is better than N/A right?

   If this carnival thing isn’t working for you, keep in mind that if you have an iPhone with a crack in it but you still use it, you are already operating with the same principle. Because clearly you value the experience of using it even if it isn’t *~*pErFeCT*~* (and if you have an iPhone without a crack in it, who even are you?)

   Okay now that we understand the core logic for anything else to make sense, here are the top ways you can have fun in a city that doesn’t quite feel like home (and yes I will limit further analogies and parables cuz clearly I’m not as good at it as Jesus was).

   

2. Say no to fast food and delivery.

   Food is the easiest way to gain insight into a new culture. When you eat out more, you’ll see more people, notice trends across different menus, and you’ll overhear similar conversations. All of these things help give you context when navigating a new place and give your great material for conversation topics. For example, Aussies love their burgers and their rivalry with the New Zealand All Blacks in rugby is palpable. While the Quarter Pounder at McDonald’s is both a staple in diets both at home and far away, branching out to try foods you haven’t tried before is an experience in itself. When calling in takeout, it isn’t rare to eat while watching TV in your hotel room — all of which your brain registers as common and similar to the way you normally eat. With such similar experiences lasered in your memory, you’ll leave the trip feeling like you didn’t do anything new or adventurous. And if you don’t believe me, believe science.

   If you’re looking for confidence when eating alone, OpenTable recently noted that dinner reservations for 1 person have gone up 85% since 2015. EIGHTY FIVE PERCENT.

   If you want to do what’s best for your bod, there are multiple studies that say eating with or simply around others helps you eat healthier (oddly, it’s mostly because you eat more veggies when you’re with people — which makes sense I guess because that plate of yellow I load up with 97% carbs and 3% bacon is always slightly embarrassing for me). And being more relaxed when eating and drawing those positive vibes from the people around you can also increase your heart rate variability and activates your parasympathetic nervous system to allow your body to better absorb the nutrients from the food you’re eating. In addition to controlling digestion, this system is also in charge of that sexualllll heaaaalllinnn’ Marvin Gaye sang about. So oysters being an aphrodisiac — yep, that’s your parasympathetic nervous system. Wow — look at all the facts!

3. Do normal, boring things in public.

   Take a book and read at the local coffee shop, grab your notebook and go to the park to start writing the outline for that company brief you have to work on, or grab a drink while writing in your travel journal. Whatever the boring thing is that you need to do, make it a little less horrible by going somewhere new and working on it in public.

   Personally, I think this was super effective because it helped me see and do as much as possible outside of my hotel room, which is essentially the whole purpose of traveling (I mean let’s be real, if you’ve seen one La Quinta, you’ve seen ‘em all). It also gave a purpose to my outing and allowed me to avoid feeling self-conscious by sitting idly or scrolling mindlessly through my phone as I waited for my food/coffee/drink/second glass of wine order. And if I did have work that needed to be done outside of my standard hours, I wasn’t bitter about being cooped up in a hotel room.

   

4. Ease in with shopping.

   Okay, if you aren’t quite ready to fly solo at dinner, there is literally nothing more socially acceptable than shopping alone. This is a good way to explore a new city by yourself and see what the style is in another country (because surprise: socks and flops are apparently a thing). It’s always a bonus when you get to a place where the salespeople have regional accents, too because you’ll pick up on new terms you don’t typically use. Case in point: sliders can in fact be a type of sandal and not a miniature burger.

5. Call your pep squad.

   So I went to a James Bay concert by myself. I actually had so much fun and I swear I am not just saying that (because srsly if it sucked, no one would ever know and I could just not ever mention it — trust me I have thought about this). BUT I think the reason it was great was because I went to it with pretty shit expectations (expected fun level: 2.47)

   To get the courage up and to decide if I should even do it or if attending would validate my lameness, I called my ultimate pep squad: the ‘rents. Talking to the people who encourage you to take risks and want to see you living your best life is the ultimate way to pump yourself up because — in case you haven’t noticed — the person that gets in the way of Operation: Best Life the most is yourself. So listening to my parents who have my best interests in mind was kind of like using the phone-a-friend helpline from Who Wants to be a Millionaire. They provided rational perspectives on the best and worst case scenarios and gave me a dose of confidence that allowed me to walk directly out of my comfort zone and into one of the most memorable experiences I had. I walked out of the venue with a level of confidence I really haven’t felt before and absolute sureness that no experience on my trip would have to be sacrificed because of my solo-ness.

   

6. Research local events and classes.

   Until you’ve gotten to know people, finding something to do on the weekends is probably the hardest part of traveling to a new city by yourself. But lucky for us globetrotters (lol not the basketball kind), there are platforms to help with this, like Eventbrite. Let. me. just. say: Eventbrite is so great for this. They have classes on essential oils, bread making, macrame, languages — literally everything. I took a Food Styling course with For Foods Sake, and in addition to making some of the most beautiful waffles of my life, there were some really cool people I got to talk to.

   In addition to Eventbrite, I swear I have also never looked at promotional materials more critically than when I was in Sydney. Posters at coffee shops and flyers tacked to street lights at crosswalks became regular reading material, so keep an eye out for those too. And even though you might think the local magazines hotels pass out are completely stupid, they are super helpful for learning about events happening in the area, so take advantage!

   

7. Do it for the ‘gram.
   

   Instagram has been giving me some v weird recommendations for videos to watch lately (no, I actually don’t want to watch someone making tiny food or cutting through playdough with a chopstick … *5 minutes later* … “oh my god those french fries are SO SMALL!!”)

   IG, as much as I take these weird recommendations personally, I still love you because you appeal to my shallow lower self. And now that I am aware of that lower version of myself, I will exploit it as frequently as needed, so thank you.

   So if you need a reason to get out of your hotel room, even when you don’t have anything to do, even if you’re afraid you’ll look like a total loser going solo, tell yourself you should do it for the ‘gram.

   

8. People kinda don’t care about you.
   

   So this sounds harsh, but it’s catchy and kind of true, so just indulge me for one second.

   I had one of my very wisest friends call me out on my shit one time and I will not ever forget it. I was in a workout class feeling like an idiot, and as I was mentioning how dumb I felt like I looked, I remember her saying “do you really think everyone walks around all day thinking about you?” I hadn’t really framed it that way in my head, but omg did I just get slapped or what. She was totally right. People didn’t wake up at 5:30 AM to go to that class so they could watch me swing a kettlebell, and it’s pretty self-indulgent to think that. The same principle applies when doing things alone.

   If you haven’t had someone tell you, here is the truth: people care 0% about what you look like sitting by yourself while waiting on your food. They just don’t care. And they have other things on their mind besides you. Most people are constantly focused on their own experiences, and as soon as you are able to do the same, the more fun you’ll have. And I really promise, it is so worth it in the end.