Journalism and dating: transferable skills?

A journalist friend of mine once said that going on dates with strangers is like interviewing a source. You show up, keep things light and breezy while delicately accumulating all the data points you need. I mean, ideally, along the way, you have fun, too.
Besides storytelling, the journalistic skill that came most instinctively to me was interviewing people. I know how to ask the right questions, and how to gently and unobtrusively steer a conversation in a way that delivers the goods. I know how to build trust, how to shut up and listen, how to encourage in the right moments, and stimulate if a conversation feels to be running dry.  
I know how to shoot rapid fire, sharp questions with the intellectual fast talker types who seem to need that rhythm and tension to pay attention to me, but also, when to play ‘dumb’ enough to get eloquent quotes and not convoluted jargon. And I know when to start being that little bit difficult and annoying if someone who owes me an answer is being evasive. My mentor, Joyce, who used to be White House reporter, said that when she interviewed officials, she’d often deliberately ignore social cues. 
“People would get so uncomfortable, they’d just say anything to get rid of me”. 

Of course, the key difference between going on dates and interviewing sources is that only one of those activities is supposed to be in service of a story with your byline on it.
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Recently, I was at a bar with some friends where I wound up talking to this guy for three hours. I got that look your friends give you when they think you think you’ve met someone pretty cool -- when actually what has happened is that you’ve discovered you’re talking to a recovering firebug and DIY napalm expert and you want to learn everything you can about their little hobby. 
Through the course of that evening, I found out:

1. How he first got into making his own napalm, what this process entails, and how available this information is now and was when he first got into it as a teenager.
2. What his triggers and drivers were, whose homes he targeted and why, how much impunity he enjoyed when he was caught and the extent to which this was tied to his privilege.
3. How and with whom he operated, what his co-conspirators are doing now, and how he, ultimately, managed to shift these destructive energies into the more constructive work as an entrepreneur.

For the record, I had disclosed early on in our interaction that I was a journalist, and, in fact, he  was the one who pushed for the interaction to be pursued at a later date with the aim of a story coming out of it. He said he felt like I really understood him. 
At that point, I felt kind of guilty. I wondered: Did I really understand him, or was I just really good at making him feel understood so that I could satiate my own curiosity about him?
As I read this back I also think, what if I was the one who was actually getting duped that whole time and he’s not a firebug but a pathological liar who’ll say all sorts of stuff to pique and sustain a journalist’s interest? 
For anyone who is interested in the power games often at play between journalist and subject, I’d recommend Janet Malcolm’s The Jounalist and the Murderer, a seminal work in the murky ethics of our game and a must read for anyone in our industry who wants to do what we do with something approaching a clear conscience.
Malcom interrogates the work of a journalist, Joe McGinniss, who covered the trial of Jeffrey MacDonald, a man accused of murdering his own family.
In putting together his book, McGinniss got the convicted murderer on side by lying to him that he believed he was innocent, when in fact what he published was a damning story of a ruthless psychopath. 
Malcolm meticulously interrogates the trial and how it is reported. She interviews the documents  McGinniss accumulated, studied, and transformed into the material he needed to support his thesis.  She also interviewed the accused murderer -- who claimed innocence  -- to gauge his character herself, and found what I love about her work: no definitive answers about who he was and whether the evidence against him stood up.
She observes rather a person “characterless” enough to serve as a canvas onto which McGinniss could paint the perfect murder story, and sell a lot of books. There’s a really nice passage she has about the work journalists do in interrogating our fellow humans as we commit their story to paper. 
She writes that the truth is people aren’t characters in books -- they’re a lot harder to pin down than that. They change, surprise us, confuse us, bore us, behave in different ways with different people, contradict themselves. The rules we apply in trying to make sense of them are never that stable. 

Fun, isn’t it? To be one tenth of one’s way through project 100 dates and already drawing parallels between your own ‘research’ and the study of an accused murderer. The thing is, I haven’t met with any murderers, yet, I don’t think. 

But my approach so far has had similarities to how I’d report a survey-style story, mostly because I’ve set myself metrics that require efficiency, and I’ve tried to maintain an open mind about my sample set. The thing I like especially about the fact that this is all happening via apps (something I haven’t really done much of before because, well, Stranger Danger), is how easy and uncomplicated it is to back out graciously.
To keep myself stimulated, I’ve tried to gamify the process and make it feel like an adventure. 
“Set me a challenge for a date to go on,” I asked one of my one of closest male friends.
“I can’t. If something happened to you, I couldn’t forgive myself,” was his reply. 
“I mean, don’t say “date a serial killer!” I replied.
“Yeah, fair”.
I realised I might be being a bit too gungho about all this when I was chatting to someone about prospective cool abandoned spots to explore with only a cursory scan of their profile, which as it turned out had one of those weird contrarian rants about pronouns and vaccinations on it. Imagine that. Wandering around a decaying swimming pool with a stranger convinced that having asshole opinions makes him cool. I’d rather date a recovering firebug. 
I think, the thing is, part of me feels like I am peering through my “research” with the same inconclusive interrogation Malcolm applied to her study of the “characterless” MacDonald. I.e. You can apply all sorts of forensics to the romantic realm. You can interrogate your back story, scrutinize your past traumas or whatever, talk to your friend about a date in that way that they say “oh, wow, SUCH a libra”, mull over attachment theories, write a list of pros and cons of everyone you meet: “Says he likes my brain!”, “feels like I’m at a lecture”, “agrees that Tool is more complex and interesting than Rammstein”, “sends ‘wakey, wakey!’ 7am text messages that make me want to throw my phone at the wall”. 
But the reality is that there are some -- many -- questions, and some -- many -- mysteries that investigative processes just can’t resolve. And again, dating, unlike journalism, involves your having, also, to wind in the interrogation chair and face someone else’s scrutiny and investigative processes. And that, well. Maybe I should just assign myself a story about the DIY Napalm kids instead…

*I know I said I’d write something helpful about stress management. I haven’t really done that. What I will say is that one of the best lessons I’ve learnt is developing the skill of learning to distinguish between the wrong and the right discomforts and acting responsibly with regards to my own safety, despite certain “gonzo” journalistic inclinations otherwise. Might not bring the best stories, but life can’t always be about that, unfortunately.