How Loneliness Levels the Playing Field

“Are you in charge of the music?” an older, balding man asked me at an event I had helped plan. He must have been nearly 40. I was 26.

“Yes,” I said smiling, trying to hold back a sarcastic comment, because clearly I was. My phone was attached to the aux chord. I was attached to the phone. But I smiled, because I always try to be friendly when I’m involved in an event. We made small talk for a minute. He told me he was from Queens. I told him that’s where I work, and then I made up an excuse and walked away, because although he was nice, I knew the conversation wasn’t going to lead to anything more than small talk. During this time I was texting a guy I had just gone on a date with. It was in between dates 1 and 2, and before turning away from the Guy, I shot my date a quick text.

“I think an old man was trying to hit on me,” I texted.

“Humble brag,” he texted back jokingly. And then I returned to the party to find my friends, laughing it off.

And then 20 minutes later, when I returned to my phone, so did my admirer.

“So since you work in Queens, maybe I can have you over at a coffee shop one day?”

I was confused. I assumed he was asking me out. Now I’ve never tried to ask someone out, but that has got to be one of the weirder ways to do it.

“You own a coffee shop?” I asked. And I know it was mean, but who talks like that?

“No, what? I want to have you at a coffee shop in Queens.”

“Are you asking me out?” I offered some help, feeling slightly bad at my initial response.


“Oh! Thank you,” I responded, somewhat meaning it. It’s hard to ask someone out, especially in person. Especially when said person is at least 15 years your junior. And I had to give him props for confidence, I guess? Even if he didn’t know what he was doing. “But I’m actually dating someone,” I lied, because it seemed easier than the truth. And I made up an excuse about the music and turned towards my phone. I thought that would be our last encounter.

And then, as if it couldn’t get worse, he came back for round 3.

“Are you sure?” he asked.  “Are you sure you’re dating someone?”

Well I mean, no I wasn’t sure, but what kind of question was that?  “Yup” I answered. “Very sure.”

“Oh,” he said.

“Yeah. But thanks”

“You’re sure?” This guy was relentless.

“Yupppp” I said and wiggled my phone for effect- hoping he’d get the hint of some imaginary boyfriend on the other end.

“Maybe you know someone else for me? Do you have a sister?” he asked.

I almost died.

“I do not.”

And then, just in case I thought the night couldn’t get weirder, he decided to prove me wrong.

“Are you sure?” he asked.

Hand to god he asked if I was sure if I didn’t have a sister. Look, the boyfriend thing I sort of get- maybe he could tell I was making it up? But I was 26 years old. I have 3 brothers. That’s it. If I went through 26 years of life unsure of whether or not I have a sister we have some serious, serious problems.

“Am I sure that I don’t have a sister?” I asked. “Yes, I’m very sure.”

And so began the weirdness. Later that night another older guy told me I looked like some actress.

“OK,” I said.

“I don’t remember her name,” he said in a thick Israeli accent, “but she’s in movies with Leonardo DiCaprio.”

“So every actress,” my friend answered rolling her eyes as she pulled me away.

“You’re too nice to these people,” she said to me.

But that wasn’t it. I hadn’t been nice at all. If anything, I’d been kind of mean. They were the ones putting themselves out there. And sure, a part of me had been creeped out, so I let my sarcasm do its thing, but I wouldn’t say engaging with them was being nice.

You see my first reaction from guy number one was that I was kind of offended. On numerous levels. Sure it’s nice to get hit on. But not when a guy is nearly double your age. And not when he tells you he’s even willing to date your nonexistent sister. Because then you suddenly become easily replaceable. Just another girl in a lineup who can fill the role of girlfriend or wife.

But in retrospect, I realized that’s not what he was saying at all. He wasn’t looking for anybody. He was looking for somebody. And that is an important distinction. Because if you’ve ever felt lonely you know what it’s like to feel that small tug of desperation that makes you want to do crazy things like ask a random girl, “but do you have a sister?”

So even if the encounter made me want to laugh at the absurdity of it all, and cry about the fact that no one I was actually interested in was hitting on me, and only 40 year old men were coming up to me, it also made me realize how profoundly alone we all were in that room. With varying levels of “game,” some of us were working the room with ease, others were hiding in corners trying to figure out how to string words together to properly ask a girl out. And there is something deeply equalizing about that, no matter how old or how cool or how cute you are. He was no worse off than I was. If anything, maybe he was doing a little better. At least he was putting himself out there. I spent the night mingling and then retreating to the corner to “check” my phone. It was a fail safe, an easy excuse to be alone without looking alone. Had I started a conversation with anyone new? Had I tried to ask anyone out?

Quite the opposite. I mocked the one guy in the room, who put himself out there for me. And I don’t regret saying no, because we should not have gone out with each other, but maybe toning down the sarcasm would have been nice.

My natural reaction when I’m not interested is to always be on guard. To crank up the sarcasm and to assume a guy wants something from me. That he’s creepy or strange, and there’s obviously a basis for that line of thinking, but there’s just as much reason to remember that women aren’t the only ones struggling through this dating process, putting themselves out there, feeling self conscious.

If I’ve learned anything from dating it’s that dating: going on dates, not going on dates, breaking up and trying to get together, is lonely. Even when another person is sitting across the table from you. Even when your best friend is going through the same motions.

Loneliness is the great equalizer. And it’s easy to forget that regardless of gender, age, looks, religion, job status, we’re all in the same boat, of feeling a deeply lonely experience that is in some ways completely the same as the next person, and in others wholly unique. And so, sometimes, a little compassion goes a long way.

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