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How to Date Yourself: 4 Beginner’s Rules to Vacationing Alone
by Arynetta Floyzelle
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December 17, 2018

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How to Date Yourself: 4 Beginner’s Rules to Vacationing Alone

Senior Editor Arynetta Floyzelle
Senior Editor Arynetta Floyzelle

After months of planning, starts, and stops, I finally made my solo sojourn to Palm Springs. I gotta be honest, it was a bit of a rocky start.  The kind of rocky start that in the past would have made me doubt everything about this whole “dating yourself” enterprise.  But I am committed to persevering beyond the rut. Yes, I made a few mistakes, but I stuck with it. In return, I had a fabulous solo vacation, and based on my successes, and my failures, I figured out a few beginner’s rules to vacationing alone.    

Four Beginner’s Rules to Vacationing Alone

RULE NUMBER 1. KNOW THYSELF

One of the best things about traveling alone is that you get to make it all about you. No sharing a room with a friend who can’t sleep unless the thermostat is at 70 degrees leaving you scrounging around for extra blankets.  You can happily pop that sucker up to 80 (which I absolutely did) and sleep naked.  No having to collectively decide on a restaurant that everyone likes and can afford, you can be as miserly or extravagant as you desire. You can let the TV play all night, or keep it off your entire trip, and if you do choose to have it on, you can watch as much Real Housewives as you want.  

It’s all about you, baby.

But here is the down fall to that… it’s all about you. And this is where your habits can work against you (as they worked against me). It’s wonderful vacationing with others for many reasons. They keep you active. You could have every intention on wanting to sleep in, but a girlfriend deciding to get up and get to the pool early will motivate you to get out as well, whereas, without that girlfriend, you may have slept the morning away.  

Friends may also push you into experiences you may have otherwise passed on.  For instance, I really like to go with the flow on vacations, but my friend Star likes guided tours and the like, so when vacationing in Europe with her, I ended up on guided excursion after guided excursion.  Guess what, they were awesome. They enriched the experience so much more. Now, I prefer to be guided when I am visiting historical sites.

See, those are two great examples of things to know about yourself when you are planning a trip, that you are a lazy bee in the mornings likely to sleep the day away if you don’t have a plan, and that you like guided excursions. Fix: plan that guided excursion at the crack of dawn!  Okay, if not the crack of dawn, early enough to force you out of bed at a reasonable time.

Caught red-handed.
Caught red-handed.

Another, very important, question to ask yourself — what type of traveler are you, a Whitley or a Freddie? Chosen from the phenomenal 90s television show A Different World, Whitley Gilbert was the high society southern diva born with the proverbial silver spoon and high-maintenance to the tilt. Freddie Brooks, on the other hand, was the flower child “anything goes” hippie of the bunch. She was a low maintenance, laid back, down for whatever lovelutionist. Freddie would be happy vacationing in a trailer park as long as she could see the stars clearly. Whitley, however, needs a lovely locale, with fabulous restaurants, room service, and plenty of additional amenities.  She is five-star (at least) or bust… as am I.

When traveling, I can be a bit of a kind and lovely diva. Kind and lovely because I do my best to be polite, I truly enjoy making things easier on people, I fully understand when a mistake is my fault and I don’t mind paying for it (for instance, I don’t do dairy, so if the menu says there is dairy on a salad, and I forget to ask for it with no cheese, I will still send it back, but I am completely okay with paying for two salads, and if it is taken off of my bill, I will often leave the cost of that salad included in the waiter’s tip). But the diva part is that I want what I want, and I don’t want to feel bad about it. I love to be persnickety on vacation and I prefer to stay in locations that consider customer service their strong suit (and love to deal with lovely divas like me).

When vacationing alone, knowing these things about yourself is essential to guaranteeing a decent time. And what can make a decent time wonderful is planning.

RULE NUMBER 2. KNOW THY PLAN

So, here is where my own weekend began to crumble before it even started. Three months ago, when I concocted my Palm Springs vacation, I started out so strong. I Googled the best Palm Spring Hotels, then canvassed my friends on the best places to stay. I googled and canvassed “things to do in Palm Springs”, I checked the Palm Springs weather for the weeks I intended to go. I planned my outfits. Three months out I was gangbusters.

One week out, not so much. After several starts and stops, the week leading up to “Me Day” were packed and hectic.  I didn’t even have my hotel. Of my hotel search, two kept recurring. One was very pricey, and though it looked amazing, I wasn’t sure if I wanted to spend that amount, especially my first time out the block and with my planning falling apart the way it did.  The other was the Ace Hotel and Swim Club.

I didn’t even book until 30 hours before, and those 30 hours were so relentless of my time, that if it wasn’t for the hotel’s one-night charge cancelation policy, I would have changed my mind.  I hadn’t planned my days, hadn’t shopped for my solo gal weekend wardrobe, left four hours late, and arrived at the hotel around 9pm, to *gasps*, no valet or baggage service!…   

Oh, did my inner Whitley boil, while my outer Arynetta resolved to hang in there.

Looking back, I am sure that if I would have asked one of the two lovely hotel clerks to help me with my luggage, they would have.  Instead, exhausted from the drive, upset that I’d gotten in too late to enjoy the day, hungry, and cold, I dragged my bags up a flight of stairs (no elevator, calm yourself Whitley).  And quickly made my way to the Amigo bar.

Courtesy of Arynetta Floyzelle.
Courtesy of Arynetta Floyzelle.

Once there, the loneliness deepened. I found it hard to settle into my safari a la single girl surrounded by girl groups enjoying holiday Friendsgiving vacays. My heart kept leaping to the fun my girlfriends and I would be having.  When I found myself eavesdropping on two women, vacationing from the fam, chatting it up with a lone guy there to finish writing some songs, I realized I was experiencing a weird kind of FOMO — I was at the event, but feeling like I was missing out on the experience I assumed those around me were having. Feeling awkward and alone, I resisted the urge to hide inside my phone and talked myself out of fleeing back to my room.  

Once my Malbec and fish tacos (absolutely divine, perfectly fried, ordered without the shell) arrived, I remembered my promise to myself in How to Date Yourselfstay out of the hotel room. I headed out to the patio. There, flanked by a couple playing ping pong and guy group playing corn hole, I drank my wine and ate my tacos, second guessing if I was the type to travel alone the entire time.

Moral of the story is…

Using what you know about yourself, make a plan and stick to it.

I know I am a last-minute person. So I should have started packing Thursday night, and left out first thing in the morning on Friday, especially since the Ace lets you begin enjoying their grounds immediately, while holding your bags and getting you into the first available room if it’s before check-in. Fix: I could have planned an activity that started at a certain time on Friday that I had to pay for ahead of time, (bonus if cancelling within 24 hours meant I would lose my deposit…know thyself). That would have gotten me there and prepared.

In hindsight, I totally get why Ace Hotel doesn’t have baggage service. It’s one of those places where you get to disappear into your experience, none the wiser — not even the front desk staff.  But you definitely want to know this ahead of time, so as not to start your experience in a salty mood. Especially if you are by yourself. Bad mood plus loneliness is no way to begin your vacay.

But, despite inauspicious beginnings, I’d arrived, and by golly I was going to make the best of it. And the good thing was Ace Hotel was going to be with me the entire way. I had chosen the perfect location, and if you are traveling alone, you should do your best to, too.  

RULE NUMBER 3. KNOW THY LOCATION

Courtesy of Arynetta Floyzelle.
Courtesy of Arynetta Floyzelle.

So, high-maintenance wise, I am definitely a Whitley, but I have a little bit of Freddie in me, too. I’m a “go with the flow” flower child at heart who is most comfortable when I know that the flow will meet all of my needs, at least when I am on vacation. And The Ace Hotel and Swim Club absolutely did.

The Ace is a boho glam oasis parked in the middle of the desert. The restored two-story mid-century building sports an organic spa (a necessity for me), organic roadside diner (organic food, also a necessity), vintage photobooths, hidden speakeasy-esque bar, open for service ice cream truck, commune, two heated salt water pools and a hot tub, bike and scooter rentals and more — all which make it very easy to, as the website encourages…

“Relax enthusiastically.”

It’s the type of hotel with something scheduled every day from Mellow Yoga to Drag Queen bingo. It seemed to be fashioned more as a retirement community than a hipster playhouse, which made it the perfect hipsters playhouse. It’s, as Ace puts it, “The desert home to freethinkers, wanderers, mystics, and artist.”  

Well, early Saturday morning this free wandering, freethinking, artistic, mystic was up, fed, and on her way to her pre-planned mellow yoga class, and from there, straight to the pool. I had figured out my Saturday much better than my Friday, and I gotta say, it made all the wonderful difference. And because I did manage to choose a hotel with my top amenities in mind, my solo vacation turned around quick, fast, and in a hurry.    

Noon found me luxuriating poolside in my bikini sipping a hot toddy next to trucker hats and tattoos, animal print one-pieces and tortoiseshell glasses (rocked in the truly fabulous way that only a sensational woman of a certain age can rock), silver haired foxes, silk robed fashionistas, momma and poppa millennials, and the rest of the beatniks lounging in their Ace issued robes as Stevie Wonder tunes spoke directly to our sun soaked souls.  

Within two hours, I was chatting with Michael, a lovely Palm Springs native who was a member of the Swim Club, Spa and Gym. Get this, Michael told me he’d decided to join the gym because it played vinyl records — talk about details. He gave me a little history lesson on Palm Springs being the Modernist hub of the world that lost its way in the 90s, but during a renaissance period toward the end of the 90s, the city decided not to renovate, but to restore itself to its mid-century height. He also pointed out the best view of the snow-covered mountains — visible from our deck chairs — before heading home with a final wish that I enjoyed the rest of my vacation.

Scared of the “fish out of water” feeling I’d had the night before, I’d come to the pool loaded with work and podcasts.  Finally, I abandoned fear.  With the snow-covered mountains smiling upon me on a 72 degree day that under the desert sun easily clocked in at 85, being serenaded by Ace Hotel’s very gifted DJ, I had one simple thought… f*ck yeah, Palm Springs.  

As day slow-faded into evening, and the playlist relaxed into a fantastic fete of old school R&B, I was happy that I’d committed to this plan. The weekend had turned for the better. My choice for my solo vacay was a wonderful idea.

Courtesy of Arynetta Floyzelle.
Courtesy of Arynetta Floyzelle.

RULE NUMBER 4. GIVE THYSELF A CHANCE

This leads me to my final lesson: Give it a chance, and a little time. Vacationing by yourself can be a bit wobbly at first, especially if you are used to out of town excursions with others, as I am, but give it a chance, even if it starts out a little rocky.  

I could have turned around that first night with promises of Marvelous Mrs. Maisel singing me all the way back to Los Angeles.  Unsure about the hotel, the success of this trip, and spending so much money on myself so close to Christmas, that would have been the easiest and most comfortable way out.  But I persevered, and half way into day two, I was living my best life.  

Attack by cacti, other than that, doing just fine.
Attack by cacti, other than that, doing just fine.

If you have to modify your plan a bit, modify it. I had planned to have my spa time at Ace Hotel, but then found out they didn’t do nails (clearly, I didn’t make this appointment ahead of time), so I changed to the Avalon Hotel and Estrella Spa. Heading off the Ace property gave me an opportunity to see some of Palm Springs that I’d missed since I arrived so late and let me check out another stunning hotel. My experience was fantastic and included a super fun conversation about boys, skincare, and overall bad behavior with my pedicurist. It was just the girl talk I’d been craving.

I returned to Ace, got a little work in that couldn’t be put off, ate a little room service, then headed for a late-night dip in the hot tub. After chatting with some women who’d just arrived from Seattle, and soaking up every bit of the relaxation I could fit in to my last night, I tucked myself into bed wondering where I would take myself next.     

My trip had been a success, and a new standard was set.

Vacationing alone can be daunting, but I found that in my commitment to date myself, it is a necessity. It is in the times that I put myself in situations that I have never been in before, that I have had to focus my hardest on the practice of self love as I navigate the learning curve. I love that I am constantly learning new things and accepting old things about myself, and most importantly, learning to love myself through it all.   

Click Below for Additional Articles in HOW TO DATE YOURSELF:

The 3 Simple (but Necessary) Rules to Dating Yourself

How to Date Yourself

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