Name: Denny Laine
State: New York City
Question: I recently started talking with an OKcupid woman who I’ve been e-mailing with for a week. Things were going great and we finally made an appointment to meet. Before hanging up though she said “Just to let you know, I just got out of a 10 year relationship.” I didn’t know what to say but “OK.” I didn’t know what to make of that. What did that have anything to do with me? With us? Shouldn’t we start out fresh when meeting possible mates? Should I admire her for having a relationship last that long? Or should I question her for ending a relationship that lasted a long time? Do I give myself 10 years with her to see if we would make a different kind of couple? When I meet someone, I like to think we’re starting out fresh. I would answer any question they may have from “how long was your longest relationship?” to “why do you think it failed?” I would answer absolutely anything and everything and be totally honest. I understand it’s not about me, that she’s just trying to get a picture of what WE would be like in the future. But I wouldn’t saddle anyone with something like that when first meeting them. Was that supposed to be a warning to me, a total stranger looking to see her in good faith, starting out fresh? Any thoughts?
State: New York City
Wow. Okay. First, slow down. You haven’t even met this woman an already you’re thinking in terms of “we.” You are over-thinking this, which is almost certain to lead to you psyching yourself out.
She told you about her break-up for two reasons:
1. Because she’s probably a bit of a mess and didn’t know not to say that.
2. To warn you that she’s a bit of a mess and that you shouldn’t get your hopes up.
Her lack of self-awareness will inevitably cause problems down the road.
Personally, someone like this would present a degree of difficulty that does not interest me. I’d bail.
I would answer any question they may have from “how long was your longest relationship?” to “why do you think it failed?” I would answer absolutely anything and everything and be totally honest.
You’ve written several letters to me complaining that you can’t seem to find a girlfriend and that women think you’re “too nice.” This is why. You have to understand that when people ask virtual strangers these kinds of questions there’s a reason and it’s not just curiosity. They want to find things out about you to eventually use against you in some way. They’re trying to establish just how far they can push their perspective date. If you answer these questions in any kind of detail, you risk looking weak. That is what “too nice” actually means.
I understand it’s not about me, that she’s just trying to get a picture of what WE would be like in the future. But I wouldn’t saddle anyone with something like that when first meeting them.
That’s where you’re wrong. You do not factor into why she revealed this bit of information. You’re right. Nobody should ever saddle a prospective date with something that personal. It’s inappropriate. She lacks the social skills needed to know that. That’s what makes her a liability. My guess is that she’s not looking for a relationship. She’s just looking to get back on the horse and have dates so she can get back out there. Same goes for men who offer such revelations. Except they’re also looking to get laid, since that’s what truly convinces a man that a woman finds him attractive.
This is why people should skip all the chit chat and decrease the amount of communicating they do before actually meeting someone in person. Inevitably someone says something stupid or inappropriate. You have to remember that everything you say is being put under a microscope. That’s why you should avoid discussing, among other things, dating/relationship history. That topic is a minefield and gives people far too much ammunition. The whole subject should be avoided until the two people have established a level of trust and intimacy. Let them get a first hand sense of who you are in a relationship before you tell them about who you were in other relationships.
Need I remind people that firing personal questions at someone you don’t know that well is rude. Period. Full stop. The person you meet on Tinder or OKCupid does not owe it to you to answer your probing inquiries. There are numerous obnoxious ways to test someone, and that’s one of them. “When was your last relationship” is the GrandDaddy of litmus tests. And keep in mind that – no matter how you answer – you’re screwed. Say a year ago and they’ll wonder if you’re still rebounding. Say three years ago and they’ll wonder if you’re a trainwreck. In the early stages – certainly before you even meet – you’re being asked these questions because your date is dying to find a reason not to meet you. Same goes for the stupid phone step and all the extensive Googling. They’re looking for anything that will justify their bias and ambivalence.
I will say this for the seven-hundred and eighty-fifth time: Stop Talking And Start Meeting. Forget all the vetting and just show up to that date. Google is not going to help you improve your judgment. The only thing that will assist you in becoming more situationally aware is critical thinking, and that skill can only be honed with actual in-person and first-hand experience. I’ll go further and say that all the tests and online research only serve to stunt your ability to sniff out a lie or sketchy situation.