I was talking to my Mom the other day about a date I’d recently been on.

I probably went on for five to ten minutes about the date details: where we went, what we ate, how he was great, blah blah. She listened intently-ish.

“Wait, when was this?” she asked, just as I was getting to the part where we shared a cab and he went out of his way to go by my place to drop me off – cornerstone example of Manhattan chivalry.

“Last Monday,” I said.

“A Monday?!” she squawked with the kind of tone reserved for reaction to a teenaged pregnancy. “Why would you go out on a Monday night?”

“Oh, no – not Monday night,” I said, “Monday after work.”

“Dinner right after work? So you couldn’t go home and freshen up or anything? That seems strange.”

“No no,” I said, “not dinner – just drinks. That’s what comes first — weeknight, after-work drinks.”

That was the moment where I should have lied to end the conversation. “Oh, sorry, did I say Monday after work? I meant Friday at 8pm leaving ample time to go home, freshen up, not shave my legs just to be safe, and polish my chastity belt. Apologies for any confusion.”

Instead I spent 45 minutes trying to explain the common progression of dating in Manhattan – something I’m not even sure I understand – to a woman who once said, “I can’t imagine going out with someone who’s technically a stranger.”

Here are the highlights:

“So, see, first you arrange after work drinks because you don’t want to commit to dinner or waste a weekend night out if he sucks.”

“Jess, that’s awful. Shouldn’t you give him the benefit of the doubt?”

“No. I did the benefit of the doubt thing my first three years in Manhattan. I didn’t work out.”

“Ugh you have no faith in people.”

“That’s correct. Please stay focused.” (Mom rolls eyes) “Now the first, weeknight date can lead into dinner, but only if it happens naturally. If you choose to see the person again it is for later, weeknight dinner, i.e. Thursday at 8pm.”

“That seems late to eat dinner.”

“It’s actually early.”

“I don’t understand you people.”

“If by ‘you people’ you mean Manhattan then that’s fine – we don’t understand you either.”

(Eye roll #2)

“So after two successful weeknight dates you can move into a weekend drinks or dinner considering you’re past the just-drinks barrier.”

“Fine. And what time does this dinner happen?”

“Ideally you meet for drinks at one spot around 8:00 then move to a 9:30 dinner reservation.”

“Do you really need drinks before dinner?”

“Need is a really hard word to work with Mom. Let’s just leave it at, yes.” (She makes this indescribable sound she makes when she’s disgusted) “Aren’t you going to comment on how late dinner is?”

“No, I’m just pretending you said 6:30.”

“Ah. Smart move. So, with three good dates – one being over the weekend – down you can move on the elusive day date or the really promising no-plan plan.”

“Oh this is going to be good.”

“Mom your sass is not appreciated. I’ll continue. The day date is a plan to do something casual during the day that highlights an interest of one or both parties or takes advantage of a city-based event. Examples include checking out the new exhibit at the International Center of Photography because you enjoy photography and he enjoys you or meeting up at the Big Apple BBQ Festival because you both love meat. It’s significant because it represents the desire to spend hours you would otherwise be sleeping, shopping, cleaning, or at the beach with this new person.”

“Well that sounds really nice.”

“Yes – really nice but also really rare. Now the no-plan plan usually comes before the day-date but is no less significant. It represents that fact that you’re comfortable spending un-planned time together deciding on a plan.”

“I don’t understand this.”

(That same indescribable sound she makes when she’s disgusted slips out of my mouth. Fuck.)

“It’s like he says, ‘Let’s do something tomorrow night. Why don’t you come to my place and we’ll figure something out.’ And you say, ‘Perfect, anything is fine with me.’” See? Because you just want to spend more time together doing whatever. This is very good. You don’t need an enticing restaurant or movie you’re dying to see as an excuse.”

“Ah, okay. Now what if a guy suggests something outside this ‘plan’ of yours?”

“Excellent question. It can happen and, in that case, you adjust the scale of the dating activity based on his move. So if he skips a step and, say, moves for a day date before a weekend dinner date, that’s fine — good even. But if, after a weekend dinner date he shifts back to after-work drinks — not good. I also prefer not to skip an entire step, but I approach that on a case-by-case basis.

“I see. Um, Jess, did I do something to you to make you this way?”

“What do you mean?”

“Well, you just seem sort of – I don’t know – obsessive and maybe a little over analytical. Like you’re trying to write a lot of rules that maybe you should just leave alone and just let things happen naturally.”

(I roll eyes and make that sound.)

“Mom – it is very tough out there. Very very tough – and the more lines we can draw to help make things clearer the better off we’ll all be. Also these are not my rules. These are tried and tested facts of dating culture. I’m not making this shit up.”

“Right, okay, I see. Must have been your father then. And please don’t say shit.”

Point: Mom