There are so many things about myself that my close confidantes have advised, no, begged me not to bring up with my dates. I have a pretty big mouth, so I’m no stranger to blurting out information and then lying awake at night wondering why the fuck I told my date that after watching “The Grudge,” I slept with all my lights on until the 11th grade (and sometimes still do).

I’ve always been told honesty is the best policy in just about every aspect of life aside from dating. So I wondered, could we actually make stronger connections and get fewer false positives if we decided there was no such thing as TMI? To test it, I set out to push the boundaries on my dates by sharing dirt that I’d never before wanted someone to use to shape their first impression of me.

My Dating History

The first of my three dates was at the movies — not exactly the best forum for getting to know each other — so I knew I had to pack a lot of information in the short time we had on our walk from the subway to the theater. This was my first time meeting Josh*, so we both came in with clean slates, and I set out to paint mine with tales of summer flings, bad breakups, and exes. I casually mentioned that I had gotten out of a relationship six months ago, then added, “actually, it ended pretty badly.”

“Oh OK, we’re going there,” he laughed. And oh, did we go there.

I became a rapid-fire fact machine, spewing out stories about my dating history that nobody asked for. He was pretty receptive to the conversation steering into ex territory, which I guess is normal when you go out with someone with the implicit understanding that you’re both looking for a relationship. He wasn’t as thrilled, however, when I offered to show him some of the last text exchanges between my ex and I.

“This is pretty weird,” he said. And indeed it was. Nevertheless, I scrolled through paragraph after paragraph, explaining what went down and annotating the texts as I went. As if that wasn’t already too much, I also pulled up the social media accounts of all my ex boyfriends and described each one in detail. I think it’s safe to say I lost Josh pretty soon after that. When I finally asked him how his last relationship ended, he just said that “it was mutual.” No further details, which of course, made everything I had just shared seem that much more over the line. After the movie, he said he was tired and called himself an Uber. When I texted him later that night asking if he got home OK, he didn’t respond. I’m not sure what scared him off more: the fact that I still follow all my exes on Instagram or that they all sort of look like him.

My Mental Health

I had more time on my second date to plunge into the past, as we were already two drinks in and had nowhere else to be. After we covered the basic introductions, I took a leap of faith and asked a pretty weird question: “So what makes you sad?” He nearly choked on his beer. “Like, what was the last thing that made you cry?” I elaborated. And yes, I absolutely sounded like a manic pixie dream girl out of a ’90s rom-com at her worst.

“Uh, I cried during ‘Call Me By Your Name.’

My first thought? He was either lying or emotionally stunted — that movie came out a year ago — and I’m not sure which is worse. I said something along the lines of, “I cry all the time. I cried earlier today when I saw an old couple on the subway, because I realized one of them is probably going to die soon and leave the other one all alone.” For the record, this was not a lie, and crying on the L train is a rite of passage for anyone living in New York City.

I went on to explain how watching my grandmother mourn the loss of my grandfather a few years ago filled me with existential dread for months afterwards. And how that, along with my parent’s divorce and a few other personal crises around the same time, led me to seek treatment for depression. He was silent, never cutting in during my sad-girl monologue. I thought he was going to fake receiving an emergency phone call and never come back, but after I opened up, he started speaking about his mental health, too. He told me that he usually doesn’t open up to people, especially strangers, but that it was actually refreshing to skip over the small talk. From there, our date turned into a quasi therapy session.

And while I enjoyed our date turned heart to heart, any existing sexual tension evaporated the second I caught him tearing up over his dead childhood dog.

My Life In Middle School

My last date was with Henry*, who I had gone out with twice before, so he already knew I was sort of a wild card in terms of conversation starters (as mentioned earlier, he already knew too much about my fear of the dark). So to push the limits, I made a list of things I would never want anyone to find out about me. Unsurprisingly, these things fell into a broad category I call “who I was in junior high.” Not only did I regularly make Facebook statuses quoting Taylor Swift lyrics (“Romeo take me somewhere we can be alone,” anyone?), I also took MySpace photos wearing an Abercrombie hoodie, making duck lips, and holding sideways peace signs unironically. I was the poster child for the tragedy that was early aughts culture.

To avoid underselling myself, I came prepared with archival material — pictures of myself at Hannah Montana concerts, screenshots of old Facebook statuses, and a mental list of my old AIM screen names (yes, I trademarked horsemaster720). So how did I bring this all up in a smooth and seamless way? I didn’t. Instead, I “accidentally” opened my phone up to an old photo on Facebook and asked Henry whether or not he was cool in junior high and high school. Unfortunately, he was. He played sports, had a girlfriend, and graduated at the top of his class. I, on the other hand, spent my weekends posting pictures of sad girls on Tumblr. He described me as “a Disney channel girl but more emo,” which was honestly a pretty solid character assessment. Meanwhile, the only embarrassing thing he could tell me about himself was that he went to not one, but two Linkin Park concerts. I promised him I’d take his secret to the grave, a vow I’ve clearly broken as I am now telling it to the internet. But despite me revealing all the worst parts about myself, Henry stuck around for another drink, and even told me that all this made him more attracted to me (a true hero). We’re hanging out again this week, and this time, he promised to show me embarrassing photos.

I think we too often get bogged down by what we presume are our date’s expectations. Everyone’s time is precious, so cutting out the small talk and getting to the heart of ourselves is — to a degree — usually appreciated by both parties. Personally, I’d rather find out my date hates his mom early on than be blindsided by the drama at his annual family reunion. On these three dates, I learned it’s worth being more forthcoming and seeing where it leads, especially if the result is a more honest and open discussion on both ends. Maybe next time though, I’ll leave out the photos from my underbite years.