My favorite early date is the third date. Don’t get me wrong: first dates can be really fun, but I always spend them asking questions about things I could have found answers to on a person’s LinkedIn profile (and trying to disguise the fact that I totally cyber-stalked them before the date.) The second date has its moments, too, but it normally involves at least some regurgitation of the same topics we went over on the first date. The third date is the sweet spot, because I feel comfortable enough to ask all of the personal questions that help form the seeds of a connection.

I was thinking about this before my first date with Sam*, and dreading the small talk and charted conversations that were inevitably about to occur. It would be so much easier if we could just talk about our ambitions and aspirations, rather than stick to the script on our majors or hobbies. So despite a lifetime of being told that asking a date anything too personal would deter them, I decided to go for it. My current method wasn’t producing much success, after all. 

To make this a valuable experiment, I first needed a solid hypothesis (take that, C+ in physics). I surmised that if I were able to encourage an at least somewhat personal conversation, it would make my date feel more comfortable and engaged. We would connect more quickly and strongly, have a more interesting back-and-forth of ideas and thoughts, and maybe even agree to go on a second date. Next came my methodology. I decided that I would use the laddering technique (something I’ve learned as a marketing major) to stimulate the conversation. Laddering is an interview method used to discover someone’s subconscious values and motives, which you do by asking about the “why” behind a given answer. My prediction was this methodology would allow my date to open up about their personal life and consequently feel more comfortable with me. To measure the success of laddering, I would use body language as an indicator. Leaning in closer to me, for example, would count as a sign of success.

Sam would be my dating guinea pig. We met up at a local restaurant, and we greeted each other with an awkward hug. We started with the normal questions: How was your day? What’s your major? What do you do for fun? You get the idea. His stiff body language — he kept his arms crossed — indicated nerves, which is to be expected on a first date, but the conversation ran dry after each answer, and there was a lingering discomfort between us with every pause. We were running out of small-talk topics and, after 10 minutes or so, I thought it was time for a bit of a switch up. So I pushed myself to carry out what I came to do.

I looked at Sam and asked, “So tell me, what makes you you?” I don’t think he was expecting to have to field this type of question (fair) as a look of confusion crossed his face. 

He took a moment and then responded with a cautious, “Um, well I guess maybe the fact I love engineering.” 

I became worried that my new strategy made me come on too strong, but I continued and followed up with a “why?” He started talking about his love of tinkering with machines and progressed to how his dad taught him how to fix the family car. 

I smiled and asked, “So, what really makes you, you? What crafted your values?” I was amazed by what happened next — not by Sam’s answer so much as how openly and easily he spoke. He leaned closer to me (body language alert!) and launched into details about his belief in the importance of family and always supporting one another. To my surprise, Sam gave me a taste of my own medicine. With a smirk on his face he said, “I hope you are ready to answer your own questions.” And of course, I obliged with a grin (I mean, it was the least I could do). I told him about my love of art and the way Van Gogh’s paintings make me light up like no other works. Before dinner arrived, we were sharing parts of our lives and ourselves that only our friends and families really knew about. And from that, the third-date connection I craved was formed.

Any half-capable scientist/third grader will tell you one case study does not prove a point, but my results were promising. I figured out that the quality of a date is not determined by how much time you know someone or spend together, but by the type of questions and conversations you have with them. By asking deeper questions, I created a new normal for my first dates. Sam and I had space to pose the questions we really wanted answers to. Yes, it was a little uncomfortable at first, but the more I encouraged him to open up (and the more I opened up in return), the better the evening got. I think he thought so, too, as he just texted me about that second date.

*Name has been changed.