Bravely Dating Myself, One $25 Cocktail at a Time

I moved to New York alone. On the plane ride from Seattle, I made a physical list of everyone I knew in New York, in case I ever get lonely. Guess what- I got lonely and turns out, I didn’t actually want to spend time with any of the forty-one people on that list. Forty-one people to call is more than most established New Yorkers have. 

I spent weekends wandering, until my legs gave out or until my face went numb or both (depending on the season). I started to plan my weekends around where I wanted to explore- alone. I was falling in love with my own company when I started rejecting plans- to be by myself. Plans to walk the Highline, plans to pace around the Whitney Museum, treat myself to people watching and $25 rooftop cocktails at the Gansevoort, admire my reflection in well-dressed window displays. I was dating myself, creating a life that looked really pretty and romantic - romantic because I was falling deeply in love with the parts of myself I always dismissed, in case they weren’t presentable enough for someone else to fall in love with.

I’d wander and then I’d find a freeing high from sitting down to a meal- alone. Not just any meal, bucket-list New Yorker meals that felt borderline spiritual. No one to tell me what to order, no thinking about “am I gonna look like a horse shoveling hay in my mouth eating this?”, no awkward avoidance of the more expensive things on the menu out of politeness. I just had to be polite to myself and that politeness came in the form of giving myself the experiences I’d want a partner to give me. If I waited for a man to want to do all the things I wanted to do, well, I’d be pretty fucking bored.

I was out to eat one night at my favorite handmade-pasta spot, Misi- just over the Williamsburg bridge, sitting on the Brooklyn side of the waterfront. I impulsively decided to take myself out that day- for the sake of the ‘treat yo’ self’ argument and also because ya’girl kept nothing but condiments and beer in the fridge for too long (the fridge of a reluctant workaholic). 

Ooooh, girl, what power I felt walking into Misi in my deep V Reformation dress, like I was J-Lo in Versace at the Grammy’s (mind you, this place is pretty casual.) I sat alone at the bar because the nice thing about going out to eat alone is that there’s rarely a wait for one chair at the bar. I sat in the corner of the wrap around counter, prime location for people watching. The couple next to me was with their [very attractive] son who was about my age, they were celebrating their 35th wedding anniversary. The woman kept looking over at me like she wanted to say something. “I’m sorry, m’dear, did you need us to scootch over? I think we took your date’s chair.” I smiled and said, “Oh no, I’m actually alone, but thank you. I appreciate it. Happy Anniversary, enjoy your dinner!” I flagged down the bartender to my corner and asked to buy them a round of champagne. ** It’s always nice when gestures like that are well received- the champagne was poured a short while after and the family reacted like I was Oprah giving them a new car. “My goodness! What a sweetie you are!” (For full affect, imagine a southern accent here, a la Paula Deen.) “Would you care to join us? You’re over there in the corner all by your lonesome.” 

“Oh no, thank you so much, but I just wanted to help ya’ll celebrate.” My “ya’ll” came out- it’s my worst habit to pick up any accent I hear and it’s painful for everyone involved.

“You’re so brave, eating at a place like this alone. I could never. Especially a pretty girl like you, I just could never, but you enjoy...”

Brave. I cringed at that word. Brave. Amy Schumer was called brave when she posed nude for Annie Liebowitz. ( I know there’s a lot of celeb name-dropping in this post, sincerest apologies.) I spent my dinner thinking about that word- brave. I’ve never felt that inhaling noodles and wine-tasting was any sort of courageous act, but maybe it does take extra strength to decorate yourself in your Friday night best and sit alone while strangers wonder what might be wrong with you - or maybe they don’t think anything because no one cares.

I’ve learned that most women won’t go out to eat alone or do a lot of other things alone out of this horrifying thought - “But what will people think!?” Nothing. They’ll think nothing. Or they’ll think “I wish I could do that” or “good for her.” 

Dating myself felt sexy. I’d get dressed up for myself. Keep my phone in my purse, read a book, maybe charm the kitchen into bringing me a few bites of dessert on-the-house. And people might notice, they might not. Dating yourself is the one thing I ever did for myself that was just mine and no one else’s- it was none of my business how it looked to anyone else. 

I won’t tell you these dates didn’t feel lonely and I won’t say I didn’t have moments of wishing I had someone to fight over the bill with, to play footsie with, share food with or share a pocket with on the walk home. I made myself a priority for the first time I ever felt I had permission to, so that I could know firsthand what I wanted. This time in my life was the time I needed for myself so that any time I jumped into a fun, steamy relationship, if it was missing these other pieces, I’d know how to walk away because I’d think about how much joy I felt with my own damn fine self. 

If not for this phase of my life, I wouldn’t have fallen as deeply and passionately in love with my city. I didn’t know how to sit still in the discomfort of loneliness so as long as my feet were willing to move, I walked and let my eyes be my compass, moving towards whatever looked and felt like somewhere I wanted to be for a few minutes or hours. The monologues my eyes wrote in my brain have become my favorite stories of my early days in New York, stories I have yet to write down but I remember vividly. 

My heart needed me to learn to date myself more than anything- without compromise, without judgement, but with a fearless independence that was sexy by accident, because I was getting to know myself without trying to impress anyone else. I think I’ll always need these solo dates, even when I’m partnered up, dripping with diamonds, children and puppies (ah, the dream). 

My wish for you- Date yourself, regardless of being single or taken. Take note of who you are in those moments and how you feel. I realize this is all a bit cliche and I’m not the first person to shout this not-at-all-new but sage advice. (Everyone’s doing it and you should too!) I actually don’t think enough people do it, maybe because we keep being told to do it. I’m hardly an expert but if you do nothing else I ever tell you to do (because what do I know), take yourself out to that place you’ve been dying to go to. It’s lonely, uncomfortable, librating, awkward, reflective and really worth the $25 cocktail.