Dating Quandaries Over Which I Often Puzzle, Part One

Posted on July 2, 2010


Is it really okay for a woman to make first contact, or does this set up some kind of power imbalance which the whole rest of our interaction will be devoted to repairing?

How soon after a date should I expect contact, and what do the varying time frames mean? Does a next-day text mean he wants to date, with an eye on a relationship, and an email a week later mean he’s only in it for the booty, or for very casual hanging out? If I reach out, does it make me seem confident or clingy? (This is the dating gamesmanship I hate the most. If I want to talk to someone, why can’t I just do it without there being fifty hidden meanings? Sometimes a text is just a text, a call is just a call. Or is it?)

Who pays on the first date? (I have opinions about this that deserve their own post.)

How soon is too soon to talk about sex? How soon is too soon to have sex? Does sex on a second date automatically mean that this will be a relationship primarily based on hooking up, not the hope of something more emotionally complex?

How soon should I expect to meet someone from his real life? If a lot of time elapses before this happens, what does that mean?

How soon should I introduce him to my friends? I tend to want to keep my dates all to myself in the early stages–I can see my friends any time–but sometimes this means that there is too much build-up by the time introductions are finally made.

How soon is too soon to talk about kink? I think there should be a scale of kink, and part of a first date should be mentioning your number. I am working on developing this scale (The Kinksy Scale), which I know will make me rich and famous a la Kinsey. I’d also like to know my date’s Myers-Briggs personality type up front (I’m a classic INFP).

How soon is too soon to ask about past relationships and what ended them? I hate this question myself, having not one decent past relationship to my name, so I never ask. But I’m surprised at how few of my dates ever inquire. My sister says this is because guys prefer to think that they are the first person to ever date you.

If someone asks me how many people I’ve slept with, do I have to answer? And do I have to tell the truth? Does anyone ever tell the truth, or do women always lowball and men always exaggerate? How many partners is it reasonable for a sexually active 35 year old woman who’s never been in a long term relationship to have had?

How many dates must occur before it’s not okay to just disappear–before some sort of "this is why I think you’re icky" conversation must take place? (I say more than two in a short time span.)

Anyone have any good answers, or better questions?

Posted in: Dating, Online Dating