Every single person in my New York City Friend-Zone was cherry-picked from the World Wide Web. “What a time to be alive!” I just really enjoy saying “oh, we met online,” utterly deadpan, when somebody asks how a friend and I know each other.
Since I was a kid, the sum total of my American dream was to have “M Stewart” on a New York City door buzzer and to belong to this town. It is my spiritual home. The city so nice, they named it twice. Right before my 25th birthday I used my nest egg to move across state lines into a sun-drenched bedroom on 22nd Street with strangers I’d contacted via a fun webpage called Craigslist dot com. I threw down an area rug, hung up all my fabulous dresses I never found an excuse to wear, stubbornly struggled to put my new duvet cover on all by myself, strew books and picture frames on my windowsill, and lined up my toiletries on my designated shelf in the medicine cabinet. K, I’m here!!!! Now what.
Two months ticked away and I plunged into hermitude. This was not the New York experience I’d forecasted for myself. I was a shut-in. I was burnt out from work and my two-hour epic poem of a commute, spending money like it was going out of style, and I had no clue how to organically make friends. I lurked at JackRabbit running clubs and Housing Works Bookstore readings, but it’s hard to forge insta-relationships with strangers when you SUCK at the tennis match that is casual small talk.
However! I DID have an active Twitter account — with an assemblage of rad, well-adjusted, likeminded NYC-based followers who might be down to hang out with me. Like, in the flesh. The first time I met someone IRL from Twitter I was a wallflowering nervous wreck. He and I had traded witty quips back and forth for ages and finally I was like, “Dude. I gotta meet this guy.” I slid into his DMs. As far as icebreakers go, “What are you up to this weekend? I’d love to get a drink if you’re free,” seemed way cooler than, “Hello. We live in the same city. I like the words you write and you sporadically fave my tweets, so we definitely have commonalities. You seem like a nice person. Let’s have human contact, please and thank you. Hope you have a good day.” Boom. Friday night. Dinner rezzie made for 9PM (New York as hell!) He was excited. Tight.
I changed my outfit several times and settled on a bright blue vintage DVF number. Look at me, wearing one of my fabulous dresses I never found an excuse to wear. My roommate made me promise to call if I thought I was about to be SVU’d. Nope! Smooth sailing from the get-go, like having supper with an old pal.
Amazingly, when someone posts the froth of their personal life for months on end, you begin to assimilate a few things — we knew so much about each other! It was strange to hear his actual speaking voice after reading his tweets in my head all this time.
We got the check and made our way to the downtown Manhattan hotspot haunt du jour, breezing past a line that snaked down an entire city block. The velvet rope opened instantly for us — his buddy “knew a guy.” I felt fucking immortal. We danced it out in a humid cavernous red room under trippy lights while some It-Girl DJ pumped my favorite old-school hip hop jams. The opening keys to Mary J. Blige’s “Real Love” came on and I grabbed my face in my hands and screamed at the ceiling, “Oh my gad, it’s MARYYYYY.” I love the nightlife! It was the greatest Gotham evening. I limped home in my heels as the sun rose marveling at how EASY that had been. Look at me, coming out of my shell.
No new friends? No no. I’ve gone on dozens of Twitter IRL friend-dates since then. They’re all my kind’a people. Everyone’s a funny, driven bright young thing, part of a seemingly cool line of work, and they ooze terrific taste. They make things, try things, do things. Twitter is like this never-ending enormous cocktail party. It’s a high-energy room of free-flowing conversation between thinkers, creative misfits and influencers, and there’s a lot going on and you’re not sure how everybody knows each other.
New York can be an isolating town and we’re all just Nighthawks diner patrons hankering for a connection. Every time I’ve DM’d to dangle a social invitation, that person has been 100% gung-ho on board ASAP in harmony like whoa. Limb by limb, I’ve constructed my own NYC family tree. We look out for one other. My last two relationships started at this serendipitous square one. I recently met one of my heroes and had such a Talking Heads moment asking myself, “How did I GET here?” In this day and Internet age, you just gotta take a shot in the dark and be bold.
Also, don’t be a dick IRL. That’s my #1 piece of advice.
I’ve got it down like clockwork now: We do the ceremonial exchanging of the Gmails and pick a day and a bar. I’ll sit there with my whiskey sour trying to play it cool — better not fuck this up, Stewart — nodding along, listening intently, but what I want to blurt out is, “GAH. I really dig what you’re doing in the space. And look, you’re a real person!”
But the BEST thing is when we’re into our 2nd round and start to get a little ~buzzed~ and open up about our backstories, jobs, dreams, experiences, relationships, and all of life’s big things. Because here’s what always happens: Without fail, this person across from me slowly confesses that they have no idea what they’re doing‚ just making it up as they go, making detours, making mistakes, making missteps — but learning from them and never casting blame for how things turned out. They tell me they’re spinning their wheels, finding their “itch,” enjoying the directionless ride, and taking the good days with the bad.
We talk about our love lives. Many have gone on eleventy billion OkCupid first dates to no avail. Some are in love and navigating the next steps: moving in together and getting a shared Amazon Prime account? Some are just hooking up, casually encountering, having their cake and eating it, too. Others are still working through a delicate heartache. Cut and dry, the goal we all have in mind is cultivating some sort of relationship where both parties are good to one another. (And maybe someone to put down as an emergency contact on medical forms).
We talk about our careers. The lucky ones are hustling and climbing up the ranks while doing something they truly care about. Others are doing something they can’t really get it up for, but they stick around because it’s a “safe” job. Hell, it’s a job. They can make their exorbitant monthly rent and still be able to afford high-speed Internet service, light bulbs, razorblades, a therapist, a luxurious ride home in a black Uber SUV from Bushwick at 3AM, Beyoncé concert tickets, a pint of organic raspberries, repair costs for a shattered iPhone screen, or Seamless.com’s delivery minimums. You know, the finer things.
And that’s okay! It’s okay not to know. Because the mind is sharp and there’s plenty of time to light the first match, move forward, lean into the unknown, and take a leap of faith towards something that serves their passion. There are no rules to this thing.
They tell me they’re in the 20/30-something limbo, rolling with the punches, throwing spaghetti at the wall, treading water, assembling an identity, becoming, stretching and growing like elastic, and totally faking it while they figure it all out in this great big gaping unknown of “chews you up and spits you out” New York. This harbor city of ours.
And then I heave a great big sigh of relief and say, “Oh, THANK GOD. You, too?!”
