The Dating Issue
The Dating Issue
Written by Sophia Horowitz
Now, if you haven’t picked it up by now, these posts come out a bit after the challenge actually happens—which means a lot can unfold in the meantime. New realizations, some emotional growth, and, if we’re being honest, a handful of other ways I’ve been pushing myself that don’t involve a first date. So before anyone jumps to conclusions…
In the past few weeks alone, I’ve:
tried temporary tattoos (as someone who fears both commitment and needles, but deeply appreciates the art),Gone to a book fair alone at a bookstore I’ve admired, where I openly discussed the smut books I may or may not have read with complete strangers—and then recommended a series to my writing professor,
And forced myself to reach out to new friends for lunches and wine nights, while actively ignoring the introvert inside me begging to stay home and watch Scandal.
But one of the more fascinating challenges has been going on a first date again. So buckle up—this week is your classic dating diary entry.
Dear Diary… I went on a date.
To catch you up: it’s been a solid two and a half years since the last entry. I was never the girl going on Starbucks or Target dates in high school, hoping to give a guy my scrunchie. In fact, I can count on two hands how many first dates I’ve been on in my life.
That doesn’t mean people haven’t been trying. Why is it that the second you’re single, every man from your past suddenly reappears?
Case in point: right after this date, my high school nemesis—who I lovingly referred to as Pancake Dick—DM’d me asking how my life was going and whether I’d ever visit him. Apparently, according to him, high school was simply “one big disagreement.”
Sir—this was not a disagreement. You called me antisemitic slurs in the middle of a statistics class.
But yes. Sure. A disagreement.
Anyway, I’m getting ahead of myself.
Living with six women inevitably turns your apartment into an ongoing sociological study of modern dating. Some roommates are actively in the field, some are observing from the sidelines, and some of us are just asking the same question over and over again: what exactly are we all doing here?
Many of our conversations revolve around the strange honesty of it all. Sometimes it’s not a relationship we’re craving—it’s just a physical connection. The fantasy of a crashingly good make-out session, followed by politely sending the man on his way like an Uber you don’t rate.
That’s how we all ended up in the same place: downloading Hinge and immediately regretting it. Because it’s true that your confidence will never be lower than when you scroll through the “people who liked you” tab. Especially when some of those people are your peers. Or teachers. Or your ex’s teammates.
Yes. That’s plural.
One of my roommates and I started noticing something strange: people seem to equate the number of Hinge likes they get with their level of attractiveness. And sure, it can be an ego boost. Twelve men liked me today? Wow. I’m thriving.
But if you step back, the whole thing feels less like romance and more like a video game. These people are strangers. A like isn’t affection—it’s a swipe with a thumb. So when someone texts a lot, does it mean they’re interested? Or does it just mean he has an alarming amount of free time for a 25-year-old man?
Still, for the sake of the experiment, I shoved my skepticism aside and said yes to one of my Hinge suitors.
The date arrived, and I almost backed out four times. But my friends have decided this blog is essentially a legally binding accountability contract, so I went. Hair done. Makeup done. Cute-but-casual outfit. I walked to the Thinking Cup on Newbury Street, where—let’s call him—Simon was waiting.
After the traditional ten seconds of trying to determine whether either of us actually resembled our online photos, we got in line for coffee. Simon immediately began commenting on the outrageous price of a six-dollar hot chocolate. Repeatedly. With the kind of disbelief usually reserved for discovering taxes are real.
Eventually, I paid for my own. I’ve never been the kind of person who believes the man must pay. I work. I’m proud of my income. But considering what followed, the six dollars might have been a worthwhile investment in his reputation.
Small talk can be exhausting, especially for a certified introvert like myself. But years of being stuck on film sets with strangers for twelve-hour days have given me an unexpected superpower: professional small talk.
So we chatted about music, school, life—the usual. And slowly, I started realizing something.
Simon wasn’t telling me the truth.
He said he attended Northeastern and was pre-med in our online conversations, but was currently on medical leave—which, technically, was true. What somehow never came up while planning a date purposely between our two campuses was that he was pursuing a career as a music producer… and actually living in Maine.
A two-and-a-half-hour train ride away.
Which means this man bought train tickets there and back, but drew the financial line at a six-dollar hot chocolate. An interesting budgeting strategy.
There was also the minor detail that he was pursuing a rap career while confidently explaining that no white rappers were good. This was said by a white man who had apparently never heard of Eminem.
Now, to be fair, dating as a film major creates its own bizarre dynamic. People rarely understand what we actually do all day. Sometimes their reactions make it feel like they think our jobs are adorable.
Like: “Oh my god, look at the little businessman putting on his tiny tie to go make spreadsheets with his friends.”
That’s how people talk about film.
Simon told me multiple times how cool my life must be and how he wished he’d pursued something creative. Which is flattering, sure—but also strange. Because yes, sometimes my life is cool. But I also buy groceries. And do laundry. And answer emails. The glamour of filmmaking includes a shocking amount of spreadsheets.
(This might be why so many film majors end up dating other film majors.)
After about two hours of conversation, we went for a walk, which I expertly navigated toward my campus, where I announced I had just been called into an extremely important meeting.
To be fair, I did actually have one.
Simon texted me for three days after I politely told him I wasn’t interested. But despite Sir Simon not earning a second date, the experiment did teach me a few things.
First, it wasn’t nearly as scary as I thought it would be. A first date really is just a conversation with a stranger—one long vibe check.
Second, never shrink yourself for someone’s first impression. If they can’t handle the preview, they definitely don’t deserve the full chaotic feature film with director’s commentary and a 2 a.m. bonus scene fueled by sugar.
Because yes, I work in film.
Yes, I play multiple instruments.
Yes, I collect college educations like Girl Scout badges.
And I want someone who is just as passionate about their life as I am about mine.
And third: perhaps the best part of any date isn’t the date itself. It’s the post-date debrief with your friends.
As I sat on my couch later that night, retelling the saga of Simon and the six-dollar hot chocolate, I couldn’t help but wonder…
Somewhere between the dating apps and the emotional damage, did we forget that putting yourself out there is half the adventure? Because lately I’ve started to think trying is kinda hot.