Drawing My Dates: Iced Tea and Pinot Gris

Meeting a fellow artist who’s also struggling to make things work

Drawing by Jay Boucher. Print available.

Most dating advice tells you to “present your best self” but sometimes it’s good to find a fellow bruised soul and share war stories of the challenges navigating life and love. Early in my online dating adventure I met a woman who had also recently divorced and there was a moment where we both let down our guard and commiserated on our recent break ups. She told me of the difficulty of dealing with the destruction of her marriage while simultaneously keeping up appearances at her job. “Sometimes I’ll just close my office door and break down in tears,” she said. “I’ll cry for like ten minutes, then straighten myself up and walk back out as if nothing happened.” I said I was lucky because, since I worked from home, I could collapse in tears whenever I felt like it.

I was out of work for a number of years and, while freelance gigs kept me afloat, income fluctuation made balancing finances difficult. For the most part I acted more confident of my bank account than I could reasonably justify. After all, who would want to date my broke-ass? It’s a balancing act of trying to impress someone by paying for everything without burning giant holes in my wallet, which NYC is apt to do. This makes it refreshing to meet a fellow artist who’s also struggling to make things work.

I met an actress recently over iced tea and wine at Le Pain Quotidien and within minutes we were deep into the difficulties of making a living as a middle-aged artist and competing with younger people for jobs. How do you age in this city when there are no roles for women in their late 40s? How do you find jobs when you’re competing with people who are more than 10 years younger, twice as energized and half as jaded? While she was on the verge of getting kicked out of her apartment she actually seemed confident that she was going to pull through. I sympathized with her plight and explained that I had been in a similar difficult position over a year ago but eventually found steady work and am glad to be on solid ground. Things aren’t perfect but there’s always a way to make things work. We parted on a hopeful note and she disappeared into the chaos of Seventh Ave.

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