He and I had known each other just a few weeks, but we had formed an intimate tie. We met through a barman friend and had bonded over a questionable mac’n cheese burger he ended up sharing with me. Along the short way, and not just for his willingness to share dubious food, he proved he was an ally and a feminist.

We woke up one night and started talking. It was mid-week, and both of us were working the next day, but suddenly the world stopped, and intense conversations about life seemed the only sensible thing to do.

He picked up a discarded, almost empty beer can, and chugged.

He talked about his parents, about how stuck he felt in his job, how he felt he couldn’t see a way out. He spoke of inequality and broken dreams in this country, and how useless he felt as an adult. He made a lot of sense. None of his musings were self-pitying indulgence or narcissistic (sorry, Time magazine). His complaints and analyses all rang true.

Millennials living in the United States do not need statistics to tell us how false the American dream is. We know it from our guts, from bills we cannot pay despite working multiple jobs full-time, from the crippling debt – student and otherwise – we know ourselves and so many of our contemporaries are carrying.

But while much of this generational inequality focuses on women’s issues in the workplace – like ongoing gender pay disparity or sexual violence and harassment – heartfelt conversations with friends and lovers have me wondering what the toll of this economic new order is to be on men. I wonder how they will learn to relate to themselves, to society and to fellow human beings when the paths they have previously been prescribed are increasingly difficult to navigate.

Popular uses of feminist frameworks often put the spotlight on women, but gender questioning goes as much for masculinity as it does femininity. Both constructs imprison us with expectations, and place heavy burdens on our shoulders. That the constructs trace out one sex as dominant over the other arguably makes victims out of both categories.

Millennial men are coming of age in a world that has left them little space to fulfill what they have been taught are positive ideals of masculinity: to work hard, find a decent job and earn a decent wage, to provide for themselves and then hopefully contribute towards providing for a family; to demonstrate value by being strong, stable, reliable and present to people around them, including women.

Like many others, my late-night friend was heavily in debt. He went to an excellent public university in California. He worked hard to think about what his passions were and how he could transform them into skills. He took a chance, moved cities, trained, took on unpaid internships as well as paid work in retail to meet bills. Along the way, his paid work to meet bills became his main work. It seemed like there were no ladders out. He was living hand-to-mouth, month-to-month, and felt stuck. And suddenly, as he was embarking into his very early thirties, this, he realized, was his life.

Worthless, he told me, was the word that sprung to mind when he let his brain do the talking. He was certain he wanted a family and kids, but that seemed far away. There was no foreseeable way toward a car, or a house, let alone pension savings and school fee accounts for future kids.

How much work have we done in terms of changing expectations we continue to place on men? How much do women praise “manly men” who are able to lift and pay for dinner and offer comforting pats on the shoulder? Do we not still expect men to be strong and constant, financially able, successful in the public realm? My male contemporaries seem paralyzed by the fear they are unable to fulfill societal expectations and therefore are not worthy enough for partnership, life planning and love.

And women are not innocent of perpetuating this setup.

I recently texted my middle-of-the-night companion about some plans. And I cringe at myself – not him – when I recall the exchange. I was waiting for him to make a decision, I frustratedly texted him to pick a time and stick to it. “Man up,” I wrote without thought.

“Man up?” The text came back from him, incredulous.