So there was a date back in my wilder days that went spectacularly well. I had been pursuing this one woman – we will call her J – whom I would frequently encounter in the Austin bar and club scene for the better part of five months. While there was always an attraction there – and sexual tension thick enough to cut with a knife – things never seemed to quite work out. For a while I was becoming convinced that the only reason why she and I were still flirting was because she enjoyed the banter and the back and forth, rather than the idea that something would happen. And yet welcome1 persistance can and frequently does pay off and I finally convinced her to go on a date with me. Drinks, dinner and dancing later, we were back at my place.
Later, as we were both savoring the release of five months worth of build-up, I looked over at her. “I’m curious,” I asked casually, “when was it that you realized that you wanted to sleep with me?”
She snorted as she sat up and rummaged through her purse for a cigarette. “Pretty much from the moment we met,” she said.
I blinked in surprise. “Really?” I asked. If you’d asked me back then, I was half-convinced she thought I was fun to banter with but mostly full of shit. It was only over time that we started to move from the bantering to flirting to actual heat and furtive glances to see if her boyfriend had noticed how I’d wrapped my arm around her waist and she snuggled into me.
“Yeah,” she said with a laugh. “It was when you told me that if I gave you any more lip you were going to give me the spanking my last boyfriend should have. You’re the only guy I knew who’d say something like that to me. It was pretty hot.”
As she stood up to go smoke naked on the balcony – to the scandal of my neighbors at the time – I reached over to my notebook and jotted down some critical notes.
Debriefing my dates was a critical part of of my learning process as I was getting better with women. Whenever things had been going well, usually either defined by sex or heavy make-out sessions, I would ask what it was that I did that made her decide she wanted to go out with me, to kiss me or that we were going to sleep together. It helped me narrow down the things that worked and when… and critically, helped winnow out the things that I did that almost ruined everything.
Why You Should Debrief Your Dates
When you’re trying to get better at dating, you want to know what it is you’re doing that works and what doesn’t. It’s easy to measure your levels of improvement. Getting more phone numbers that turn into dates, dates that turn into a series of dates or even relationships, more makeouts, more sex… these all tell you that you’re improving. But if you want steady, consistent improvement, you need to know more. You need to know specifics.
You need to know just what it is that you’re doing that your dates react to.
After all, you want to be able to reproduce the results; if you think that your date’s responding to your clever banter but she’s actually wishing you’d shut up with the Monty Python quotes and tell her more about your time studying abroad, you’re going to be learning all the wrong lessons and left wondering why your next date doesn’t respond nearly as well.
This is where the post-date debrief comes in.
The nice thing about post-date debriefings is that they can apply to just about any aspect of the relationship. What made her decide that she wanted to give you her phone number? Why did she decide to go out with you when you called her? What was it about your dating site profile or that first message you sent that made him want to write back? When was it that she knew she wanted to kiss you? When was it that she knew that the two of you were going to sleep together?
Whether you’re a serial monogamist, dating several people casually, enjoying no-strings attached relationships or looking for The One, this is all valuable information that you’ll want.
It’s Not An Interrogation
Despite how it sounds, the post-date debrief isn’t an interrogation. You’re not trying to force information out of a recalcitrant terrorist who has the time and location for an imminent strike on American soil, you’re trying to find out what you did right for future use.
The key is to be relaxed. It’s an off-the-cuff question, born out of the moment’s curiosity. You’re not prying, you’re just interested in what it is he or she likes about you. Use phrases like “Hey, I’m curious”, or “You know, I was wondering… While there’s nothing inherently wrong with wanting to pick your date’s brains about just what it is she likes about you or the thing you do that’s so charming, it’s entirely too easy to come off as though you’re nakedly fishing for information.
When You Want to Debrief
It’s all about the moments. You don’t want to spring the debrief too early. At the end of a first date, or even the first kiss, it will feel like you’re conducting a survey – nothing says “no second date” like giving someone the impression that you only asked them out in order to collect data for your thesis.
Ideally, the debrief is done in person and preferably in the moment. It is possible to have a debrief over the phone, but it’s considerably more difficult. As many a person in a long-distance relationship can tell you, it’s difficult to maintain a level of relaxed intimacy via the phone. By the same token, trying to debrief a date via text or email is a fool’s game. A great deal of emotional content and context is lost via text, and instead of being a cute bonding moment, you can inadvertently sound like you’re conducting a post-exit interview with the HR department.
The best times to debrief are in the pleasant lows that follow emotional high-points. Whether it’s lounging in the afterglow of sex, or cuddling on the couch watching a movie, the best time for a debriefing moment is when the both of you are relaxed and at ease. After all, when the endorphins are flooding your bloodstream and the oxytocin is working it’s magic on your cerebral cortex, it’s a moment primed for bonding experiences. And what could be better than trying to get a little more insight into what’s going on in your lover’s head?
The moment all depends on the level of the question; the more intimate the question, the more post-intimate the moment should be. If you’re asking “Hey, what was it about my profile that made you want to write back?”, it’s easy enough to bring it up during an emotional high-point while on a date -laughing together over stories of horrible first dates past, bantering about your interests or even your mutual attraction.
More deeper, more personal questions: “When did you know you wanted me to kiss you?” for example, is best served during a calmer moments when the two of you have achieved a greater level of intimacy. You don’t necessarily need to be at the stage where you’re considering asking about exclusivity – I certainly wasn’t in the example above – but you do need to have reached past the occasional holding of hands or chaste, closed-mouth kiss goodnight.
- please note the key word here: welcome [↩]