Ah, the awkwardness of the first date. There’s nothing quite like it. At least in a job interview (where the awkwardness is about equal), it’s acceptable for the employer to ask questions designed to root out crazies.  Yet on a first date, where the ‘candidate’ stands to wreak more havoc than any other person in your life, questions like how do you handle stress are considered too direct.  So how do you get to know the important data without breaching social boundaries? I’ve got 5 questions designed to do just that.

1. Dogs, cats or neither? If the answer is neither, pay the tab and don’t look back. Your date’s capacity for empathy is questionable, which makes me wonder if you’re sitting across from someone who’s personality disordered.

2. How important is it for you to be passionate at your job? 30% of human life is spent at work. If your date is willing to spend that amount of time doing something that doesn’t turn them on, it tells me that their standards aren’t high enough (at best), and at worst, it could indicate someone who’s depressed, chronically apathetic, or who gets attention through being a martyr. Water seeks it’s own level. If you’re passionate and your partner isn’t, guess what’s going to happen to your level of enthusiasm over time?

3. How long is your oldest friendship? People who are emotionally stable tend to have longstanding friendships that date back at least 5+ years. The longer the friendship, the more opportunities there are for conflict – and conflict resolution. If your date jumps ship at the first sign of trouble in friendships, you can expect the same.

4. Tell me about a New Year’s Resolution that you achieved. Or about any goal you reached. The answer to this question will tell you so much about the person:

a)    Are they reality-oriented enough to identify areas of their life that need improvement? If not, this is someone who pretends everything’s fine when the roof is about to collapse, or someone who walks around with an extra 30 pounds pretending that their health isn’t at risk, or someone who gets blindsided when she’s laid off because for years she didn’t think her performance at work needed improvement.

b)   Do they have self-discipline? Can they take action even after the initial excitement of setting a goal has abated? Self-discipline is the skill that allows you to do a task that you don’t enjoy, which constitutes a majority of what we have to do as adults.

c)    Can they create a strategy (or can they hire someone who can)? Identifying a strategy shows problem-solving skills. That’s something I want in a partner. You?

5. Do you trust new people in your life or do they have to earn your trust over time? This one’s important. If the answer is the latter, it’s a recipe for making you jump through hoops, proving yourself again and again, and to what end? To me, it feels manipulative as fuck. You shouldn’t pay the debts of the people who screwed your date over and left them fractured.  That’s the job of a shrink. And not this one, btw. 

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