Solo Adventures Part 1: Wanna Sing a Duet?

I've never thought of myself as an exceptionally confident person.  In fact, I sometimes want to kick myself in the face for having, on occasion, borderline-insane insecurity issues: 

Did I sound stupid when I said that thing in that meeting?
Why didn't Rachel text me back? 
Did only ten people like my Facebook status because the other 1,390 thought it was less of a good idea than Kidz Bop 25, or any of the Kidz Bop CDs for that matter? 

It's ridiculous, I know. 

Last week, the insecurity monster in the back of my head started to yell at me upon realizing that I had no one to hang out with after work - on a Friday night!

Wanting to prove my coolness, I decided that I would be proactive and texted everyone I know within a forty mile radius of me.  Unluckily, no one was free (or maybe they were all just listening to Kidz Bop). 

I then bravely decided to message five different people on Okcupid with a proposal to hang out with me.  Sadly, everyone ignored my messages.  This happens frequently on this website, probably because I write things like "I am glad we both like being stoned" and "I really want kids, not in a wanting kids kind of way but more like renting them temporarily" sexy.

But five o'clock rolled around, and something in me clicked.  

I didn't need anyone else to have a great Friday night.  I could go out all by myself.  

The thought of going out alone scared me, and weirdly, that fear made me want to do it even more.  Because ever since moving up here, I've adopted the mantra of always doing the things that scare you.  For doing scary things is what helps you become more awesome.

And so I boldly strode out of my office doors onto the San Franciscan streets of 16th and Mission, planless and companionless. 

There are always colorful characters in the Mission and some often sort crack rocks in broad daylight.

I started walking, and as I walked, I started singing.  

"Wanna sing a duet?" a raggedy-looking older dude with grey stubble and sweatpants called to me.  He was just seemingly chilling on the sidewalk, as many long-time residents of the Mission tend to do.

I said, "It depends. Are you a good singer?" 

He got a mischievous look in his eye and said, "I think I'm pretty good.  I started trying it out recently and realized that I'm actually pretty damn good.  Better than some of those people on American Idol." 

"So let's sing something. Right here, you and me." I challenged. 

"Right now? Nawww, I couldn't do it."  He told me he was too shy to sing in public.  I tried to peer-pressure him, which led to a fifteen-minute conversation that included everything from Alicia Keys to Chinese food.  But mostly we talked about facing our fears.

"You just have to go for it," I said earnestly.

"Next time." He laughed.  We shook hands and he introduced himself as Donnae. 

"It's great that two totally different people can just stop and make a beautiful connection like this," he said.  "I mean, look at us!  People passing by us must be wondering what the hell is going on here." 

But more people should do this kind of stuff, I thought as I walked away.  Why not? 


As I continued my solo walk, I stopped to take a picture of this eye-catching graffiti.

Oh, that tech "scumb". 

"I was just gonna take a picture of that, too!" a kid walking a beat-up bicycle laughed.  

"Yeah, it's ah, very strongly-worded," I said.

"Yeahh, I think I know the guys that did it.  They're just haters." 

I asked him what he meant, and we started discussing our views on the new presence of tech workers in SF and overall gentrification of the city.  Mine as a newcomer, and his as a SF native. 

"To a certain extent, don't you think people are justified in their frustration?" I asked him. 

"First it was the artists.  Then, all the med students.  People are just bitter that they're not doing as well and making that kind of money." He shrugged. "We have to adapt." 

After chatting about our own lives and hopes and dreams, we shook hands and he grinned.  "Man, I love when random shit like this happens." 

Me, too.

It was only six PM at this point, but I decided to go to a bar anyway.  A karaoke bar, of course.

I walked in and hesitated a little before sitting at the counter.  I turned to the Filipino dude next to me.  

"Wanna sing a duet?" I asked.  This line was quickly turning into the theme of the day. 

"Sure," he said.

We ended up singing not one, but three epic duets over the course of the night (Wicked, Rent, and Aladdin, respectively).  I stayed at that bar for five hours and sang, got drunk, and discussed life and love with my karaoke partner, his boyfriend, the bartenders, and all of the fifty-something-year-old ladies that were clearly regulars there. 

We cheered each other on.  We sang all the choruses together.  We were a family, bonded by our mutual love of whiskey cokes and Aretha Franklin covers. 

"Good fucking job," a seventy year old man growled and shook my hand after my 5 drink Mariah Carey rendition.

"I'm drunk as FUCK!" one of the fifty-something ladies yelled after I congratulated her on her heartfelt performance. 

"This is a community... a drunk community!!" Sherwin, my karaoke partner, said with feeling. 

Sherwin, my trusted karaoke partner

After my new friends dropped me off at the BART station, I felt a sense of triumph in the evening's success.  

I think I realized things that day.

Not just the fact that apparently I will still be able to get drunk at karaoke bars when I am fifty five years old, although that is a powerful realization.

But also, that going out alone on a Friday night can be really empowering.  You don't always need to surround yourself with people you know to have a great time.  Sometimes the people you don't know are even cooler.  

With all of this technology and social media crap taking over the world, we've become more self-conscious about our actions and perceived popularity.  We've started to measure our worth in number of Likes and the speed of text message replies, and it's made us uncertain.  It's messed with our heads and made us question how great we really are. 

Sometimes we just gotta say "fuck it" to standards and social norms.  Challenge a homeless guy to a duet, discuss gentrification with a random person on the street, go to a bar all by ourselves.  Stop worrying about all the bullshit and do something that scares us.

And that is where our confidence comes from.  That is how we become truly awesome.