Doing things by myself has never been a favorite past time of mine. I always marvel at people who can go to the movies by themselves or sit solitarily in a diner. Especially if they choose a booth and not the counter. How can people eat all by their lonesomes, just staring at that empty seat across the table from them? It’s like my worst nightmare. I’m just too insecure to risk being out alone and having everyone looking at me thinking what a LOSER!

However, recently my friends have been dropping like flies. I mean, why wouldn’t they be? I’m thirty-four and like most normal people my age, they’re all getting married and moving to grown-up places like Westchester where they have backyards and like, good school districts? So it’s become painfully obvious that unless I want to live the rest of my life as a total recluse, I’m going to have to get comfortable venturing out on my own.

That’s where Texas comes in! After eleven years of promising on a bi-annual basis that I was going to visit my cousins in their not-so-new home, I decided to make a go of it and head out west to spend a couple of days in the Lone Star State. However, before I showed up on their doorstep in Austin, I opted to see how I fared going solo for one night in San Antonio first. Turns out I kick ass at being alone! Here’s what I learned along the way:

Car Rental Agencies Are The Devil

First things first. I didn’t kick ass at everything while I was over there. Particularly the part where I had to arrange a mode of transportation for myself from Austin’s airport to the city of San Antonio. If you’re a complete moron anywhere outside of the one city you live in, where nobody drives a car, talk to someone who knows about renting them before you do.

I was all excited about the $22 per-day rate I was quoted online, two weeks before I showed up at the airport, until I actually showed up at the airport and the magical wizard behind the rental counter pulled all kinds of Jedi mind tricks on me and had me walking towards my shitty Chevy Aveo (is that even a real car?!) dizzily carrying a bill for $242 for two days!

Somehow I had agreed to extra insurance, pre-paid gas, and a daily toll road charge which I thought was a steal because there are tolls everywhere in New York! Surely there would be some in Texas and paying them ahead of time was going to save me the trouble of being one of those suckers who was waiting on line to throw their quarters in the basket. That is, until I found out I was paying nine dollars a day for something that cost Texans around fifty cents per use.

Staying In A Hotel Alone Feels All Adult Like

Now for actual adults, ones who have been on business trips and stuff, I’m sure this is no big deal, but I had never stayed in a hotel without at least someone in the bed next to me and usually a couple of people on the floor, and I have to say, being alone is kind of awesome. You get everything to yourself. The gigantic bed, this big leather chair, and all of the stationary is yours to to do with what you please.

When I ordered room service, I must have moved from the bed to the chair to the desk about a dozen different times during my meal just because no one else was sitting there. Plus I kept signing for things. If I wanted a glass of wine, I’d sign for it. A Caesar salad brought up to my room? Sign for it! It was so grown up. It was just like being in one of those movies I had seen where someone stays in a hotel all by themselves.

No One Is Paying Attention To You

Look who’s super comfortable taking a picture in front of the Alamo!

Pretty much the only thing I knew I wanted to do while I was in San Antonio was go to the Alamo. It was about four blocks from where I was staying, so finding it wasn’t a problem, however approaching it was. As I made my way towards the entrance I could feel the anxiety building up in me. I was all alone. What kind of a weirdo goes to the Alamo alone?

At least three times I almost aborted the mission. I was completely out of my element. If this were Central Park it would have been no big deal because I would have been just a local out for a walk, but being that I was a tourist in a different city, it was like I thought people could smell it on me.

It wasn’t until I forced myself to stand in front of the building with my camera out, repeating “Take a picture of yourself Kelly. Kelly, take a picture of yourself in front of the goddamn Alamo!” over and over again in my head, that I realized I wasn’t on anyone else’s radar. Which was great, cause then I could relax and enjoy what is a really cool piece of American history.

A Drink Or Two Never Hurt Anyone’s Confidence

Dan from Jupiter

As if a little light sightseeing wasn’t stressful enough, now I had to get ready to hit the town for the evening on my own; a completely foreign concept to me, which was going to require backup. In the form of half a bottle of Chardonnay. I decided to sit down at the hotel bar and have a drink.

It wasn’t long before I had company. Hotel bars host lots of people who are traveling on their own and they want people to talk to as well. They even have all kinds of interesting stories. I met Dan from Jupiter Florida within five minutes. His grandfather on his mother’s side was the founder of the Piggly Wiggly food chain and his grandfather on his father’s side invented the rotary telephone. Now unless he was pulling the bullshit I do at the airport and lying to me, that’s pretty impressive. And if he was lying, then I feel like I need to consider stepping up my game from “I was born in Germany” to something more along the lines of “I’m with the NSA. There’s been an incident.”

At any rate, after two glasses of wine I was actually excited for my night out alone.

It’s Easy Going Solo If You’re From Out Of Town

If I were to go out for night by myself in New York, it would just be weird because anyone I met would be all like “Where are your friends?” but being in another city, it made perfect sense that I had no one with me. When people found out I was traveling without partners, they were even more interested to talk to me and give me the insider info on where to go in San Antonio.

I spent most of the evening in two different piano bars. One was on the riverwalk called Howl At The Moon where this guy was selling t-shirts and another was an Irish Pub called Dirty Nellys. Both were fantastic. I had so much fun.

It Doesn’t Matter If People Think You’re Weird. They May Even Appreciate It

I did two things during my evening in San Antonio that were completely out of character for me. First, when making my way back to the hotel, I found this guy playing the bagpipes. The bagpipes are my favorite, so being that I was on a total high from conquering all of my fears as well as slightly drunk from drinking all of the vodka, I hung out in front of this dude, smiling enthusiastically and snapping pictures of him for a solid two to three minutes. It was totally awkward but I don’t think he minded in the least, especially after I chucked five dollars in his tip can.

Second, I found this guy at a traffic light and said hello. I never do that. Turns out he was traveling alone as well so we stopped in at The Republic Of Texas for one last drink before calling it a night. I wish I had an interesting story to relay about him but at that point I was pretty hammered and I’m proud just to be able to tell you that his name was Jason. I think.

Waking Up Alone Is Pretty Refreshing

Sometimes when I’m on vacation, the morning after a big night out can be pretty stressful. I immediately start thinking “What did I do and who saw it?” Like the time over the summer where Jeff had to put me to sleep in a car parked outside of the party we were at because I passed out at the kitchen table or even better, the time I jumped off a moving golf cart in Puerto Rico to run from a security guard who had pulled my step brother over for driving on the sidewalk, and then yelled at him when he wouldn’t help me up after I took a header into the pavement.

When I woke up alone in my hotel room I breathed a big sigh of relief that there were no witnesses to any kind of ridiculous behavior I may have engaged in the night before. Which brings me to my next point. I don’t really recommend getting drunk on your own in a city you’re unfamiliar with. In the end, I wasn’t raped and murdered, which is always a plus, but I can’t guarantee you won’t be if you behave as irresponsibly as I did.

Also, having to drive yourself back to Austin on an interstate you don’t know with a wicked hangover, sucks.

All together though, I have to admit I’m very proud of myself for stepping outside of my comfort zone and going it alone. It’s actually made me look forward to doing things by myself in the future. Except for the part where I get the bill for all of the very adult-like signing I did for everything.

Total cost for one night alone in San Antionio: $603

Discovering you won’t completely fall to pieces if ever you have to do something you’re scared of: Pretty damn pricey!

But totally worth it.