7 Questions to Ask on A First Date

When it comes to relationships, what you don’t know can in fact hurt you.

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You know this. Your relationship history has taught you this. If you’d known [insert your ex’s negative trait here] at the beginning of that relationship, you’d have gotten out a hell of a lot sooner.

The thing is, you only get the answers to the questions you’re willing to ask, and when it comes to first dates (or the first several dates), people pussy out of asking the tough questions.

My ability to spot the end of a friend’s relationship by the friend’s third date has become so reliable that I have to physically restrain myself from rolling my eyes (or from blurting out, Hey, coming attractions: This one’s gonna crash and burn inside of six months) when I hear the stories containing the warning signs.

I don’t see the point in postponing the inevitable. To me, it’s a matter of ROI, and whether I=money spent (which I can always make more of) or time wasted (which I cannot make more of), I’ll never understand why people don’t want to uncover the truth early on – just rip it off like a wax.  

Below are the questions which, when answered, would immediately uncover red flags:

1. Why did your last relationship end?
He’s not sure?
It was mutual?
All the ex’s fault?

Run. Don’t walk. And, if your date is adept at avoiding answers, try asking it another way:
 

2. What was your role in your last breakup?
That’s an interesting question…is what people say to buy time to think of an answer, so I’m immediately suspicious.
I’ve never had a relationship means you’re signing up to be the guinea pig. If that’s what you want, have at it. I wouldn’t volunteer for that.
It’s complicated… is a less creative version of that’s an interesting question, and to which I’d respond, I prefer a complicated answer to a complicated relationship.
We’re on the break up topic during our first date? Is it going that poorly? My response to this is, Nope, not going poorly at all. Wouldn’t you prefer knowing my answer to that question tonight as opposed to 3 years from now?
 

3. What have you done to bridge the gap / grow from your last relationship?

I’m looking for a soul-searching experience here. Therapy. Relationships Skills Training, Spiritual Retreat. Silent Retreat. Something – otherwise you should expect that your date is hoping to not be triggered in the next relationship – which is nothing short of a fantasy. Relationships are triggering. Think of this in terms of career:
The person you’re interviewing says, I was fired from my last job because I had poor time management skills. You ask, and what have you done to improve those skills, to which your interviewee responds, I’m hoping this job won’t be so demanding. Enough said.
 

4. Have you ever been in therapy? Plato said, The unexamined life is not worth living. I’m here to tell you that someone’s going to explore your date’s life. It’s either going to be a shrink or a partner. Do you really want to sign up for that job? I am a shrink and I don’t want to do it for Steph (nor does she me, btw). If your date has never been in therapy, it’s not because they’ve never had a reason to enter therapy. It’s because they’re in denial.
 

5. How do you feel about couples counseling or attending personal development workshops?
I think people should be able to fix their own problems is like owning a car and refusing to bring it to a dealership or mechanic for maintenance. Relationships require skills. We are not born with those skills. We learn them in couples counseling, or in taking a relationship skills-building course.  Your date’s too proud to ask for help? Run, sister, run!


6. What are your emotional triggers? In other words, what makes you foam at the mouth, want to run for the hills, make you want to curl up into the fetal position, make you want to become destructive, cause you to stalk?


7. How are you when you’re crazy? I’m not crazy. What do you mean? When  you’re emotionally triggered, challenged, or in fight, flight or freeze mode, how do you behave?


Bonus: I also want to know how much you’d be willing to spend on a pair of shoes, an eyeshadow pallet, or a bottle of life-altering wine.

Closing thoughts: I just think if it’s ok to fuck on a first date, it has to be ok to ask these questions on one as well. OK – maybe after sex.