I Asked Only Personal Questions On A First Date

The movie Baby Mama opens with Tina Fey deep into a monologue that the viewers then discover is actually a conversation she is having with a man in a restaurant. "I still aspire to meet someone and fall in love and get married, but that is a very high-risk scenario. And I want a baby now. I'm 37. It's too much for a first date, isn't it? I said too much." The man promptly excuses himself for the bathroom, and then quite literally runs from the restaurant into a conveniently idling taxi outside of the restaurant without another word.

Yes, it’s an exaggeration, and yeah, we all laughed, but it’s a trope that speaks to a very real (and aggressively Millennial) fear — we are all of us petrified of laying our cards out on a first date, for fear of not seeming “chill”. We gloss over the complicated parts of our lives. We discuss the future in the vaguest of terms, as there’s some sort of mental block that prevents us from thinking beyond the next year. We intentionally keep our hopes and dreams to ourselves as if sharing them is somehow obligating a person we just met to agree with all of them and sign the eff up. Every turn in the conversation is a part of a well-rehearsed and conditioned dance not to put too much pressure on anything, not to reveal anything uncomfortable about yourself, not to break the fragile connection you have before you’re both emotionally invested and can "forgive" the little things you don't agree with.

And that is exact reason why a few weeks ago I found myself sitting face-to-face with a total stranger I met on a dating app and asking him, "What do you think happens when we die?"

I set out with the idea that I would challenge this notion that we couldn't fully be ourselves on our dates by running an experiment in which I aggressively was myself — and putting someone else in a situation where they had to be, too.

Before you worry too much about my poor date, he was aware from the first interaction we had on Happn that I would be coming armed with 15 personal questions, that our shenanigans were going to be turned into an article, and that he was going to remain anonymous. I even let him pick his fake name, which he jokingly decided would be "Clancy Fletcher". (To be fair, at some point in the night he changed his mind to something classier, but I'd had a few by then, so ... sorry, C-Fletch.)

I'll back up and set the scene for you. The date starts out the way most of my dates do — me, standing outside of the restaurant because I am absurdly early by nature, waiting for Clancy. I don't date very often, but I've never felt nervous about it. Maybe as a consequence of mostly dating friends or being the kind of person who frequently airs my dirty laundry on the internet, I don't feel much anxiety about holding my own with strangers. And it is right then that the familiar script starts to change — because I wave when I see Clancy cross the street toward me, and suddenly I am terrified as hell.

It doesn't help that Clancy turns out to be the exact opposite of an online dating cliché. See, I specifically chose him for this experiment because he had nothing written in his profile, and his pictures only gave me the vague reassurance that he was not a serial killer, but nothing much more specific than that. I had no chance to make any prejudgments about him, because there was almost nothing to go on. I worried that this might be a recipe for disaster, but then he shows up and is not only better looking in person than his vague photos, but is immediately engaging and friendly and goes in for a hug.

"You nervous?" I ask, attempting to take control of the situation, because I am (kind of) a journalist, dammit.

He says no, and asks if I am. I lie. He quips that he's from the New York Post and he's doing a post on this too, and I am so gullible in my uncharacteristic terror that for a few seconds, I believe him. In other words: shit, shit, shit. We are meeting on late Sunday afternoon at a diner I chose specifically to keep it casual and controlled, and already I am jumpy and awkward like an overly-eager yearbook club sophomore doing their ~first ever interview~. Unsurprisingly, we both get end up getting drinks.

By the grace of sangria and my careful, neurotic preparation for this "date," I manage to pull myself together and get us on track. I pull out my 15 questions. The rules are simple — we draw one at random, and we both give answers, no bull, no holding back. I know I won't have a problem with this brand of honesty, and it's clear in the first five seconds of this that neither will my new friend Clancy, who is refreshingly game.

Some of the questions don't seem all that difficult to answer. "What does your ideal day in 10 years look like?", for instance. But we discover pretty quickly that even the most innocuous questions take personal turns. I couldn't describe my perfect day without mentioning I wanted kids and a bestselling novel. He couldn't describe his without admitting that he wanted to travel to a mind-boggling number of places, and probably not live in the country at all by then. Even when we aren't discussing anything blatantly personal, there is some vulnerability in the implications of our answers.

Other questions are a little more weighted. I worry when we get to the soulmate question, because as romantic of a person as I am, I've found the idea of having a "soulmate" way too stifling and even a little cryptic. Somewhat surprisingly, so does he. And soon enough we realize that, coincidentally, we agree with each other on some hugely fundamental beliefs. It's not just the soulmate thing — we are both unreligious. We both decide we wouldn't undo any big mistakes from our past. We're both aggressively ambitious and proud of the hustle we put into our jobs. We're both really close to our families.

I know, I know. A lot of people have these things in common — big whoop. But it's the things we disagree on — even the inane ones like which drink we would take with us on a deserted island — that spark much more intimate conversations. Rather than just philosophizing, we start to rib each other, make fun of each other. Clancy doesn't know what Pizza Rat is and I mock him so relentlessly that a man eavesdropping at the table next to us joins in to back me up. When I profess my undying basic love for Blue Moon above all other drinks, poor Clancy almost has a brain aneurysm trying to save me from myself. In airing out our disagreements right off the bat, I find myself more at ease teasing him than I am with people I've known for years.

And then, before we know it, hours have passed — enough that our poor waitress's afternoon shift has ended and we realize she is waiting on us to close the check before she leaves for the day.

Things get straight up lawless after that. We head over to a bar across the street. We've finished the prewritten questions, but the floodgates are already open. We start asking each other personal questions off script — our past relationships, our embarrassments, what we thought when we saw each other's profiles the first time. It feels like we can ask each other anything, and for some reason that makes the comparably innocent game of 20 questions we end up playing all the more hilarious. At some point we start punctuating our points by tapping each other's thighs or grabbing each other's hands, and then we're leaning way too close to be casual, and then we're kissing in a bar.

Let me tell you something about this kiss. I am not a person who is attracted to other people easily. I have only ever dated guys that started out as my friends and grew into an attraction, so with them, I absolutely knew what I was getting into before I did. The few kisses I have had on first dates or random kiss situations have been fairly lackluster in comparison — but this? This was some damn good kissing. There was no customary awkward moment of self-consciousness or confusion, and it was shockingly natural, like we had already done it before. Whether by the magic of oversharing or some strange cosmic fist bump from the universe, I actually enjoyed a first kiss for the first time in years.

Five hours after my Super Professional Experiment began, we called it a night. I was grinning so idiotically that a neighbor low key scootched away from me on the elevator ride back up. Here was the proof that I needed that we could beat the system! That first dates didn't have to be boring and awkward and lead to more boring and awkward dates where you flounder until your ~real~ self takes over! I thought right then I had singlehandedly cracked the Millennial dating code.

But here's the cold truth sauce: It's been a few weeks since that first date, and I haven't actually seen Clancy. We did text a few times, and there was definitely an opening where we could have hung out again — but I think we both kind of implicitly knew it would be weird to do before this article came out. Still, I found myself procrastinating. I told myself I didn't have the time, that I needed to digest it — y'know, all that stereotypical writer angst we use to justify our nonsense.

But I found myself digging deep into just why I was hesitating. I went into this experiment sure that I was going to discover some life hack to fix modern dating. And here's the thing — it did work. In fact, it worked too well. Suddenly I realized that holy crap, I could actually date this person. Of course, I can't speak for Clancy — but I know it was what I was thinking in the aftermath, and the prospect of it was daunting. Confronted with a possibility that I haven't been confronted with in years, I found myself shrinking away from it without even being able to explain why.

In short, I had embarked on this weird mission to find a solution to the modern dating struggle, only to realize that I was the problem. If the mere idea of committing to a like-minded, quick-witted, charming guy I had actual chemistry with wouldn't work, then what would? In removing myself from the dating pool for so long, I thought I was somehow above the fearful non-committing Millennial clichés, but here I found myself all at once embodying every one of them. And even in recognizing that, I haven't been in touch with Clancy since.

In that sense, the experiment might sound like a failure. It doesn't feel like one, though. Sure, I found out that I am the very demo of Millennial daters I have disassociated myself from for so long — and maybe if you recreate the experiment yourself, you will, too. But that didn't make the experience any less enriching, or the awareness of myself and my weird, conditioned feelings about relationships any less worthwhile. I may not have walked out of the experiment with the potential for a relationship, but I did walk out of it with an understanding of myself that I didn't have before. As for cracking the elusive Millennial dating code? Well, it seems I've still got a long way to go.

Images: Pexels (1, 2); Unsplash (1) Emma Lord/Bustle (2)