It’s Not Waterboarding, Just a Few Friendly Questions

couple talking

Although I don’t advocate CIA-style interrogation of a date, sometimes the right question or two or three can illuminate a potential partner’s suitability.

It’s important to be creative when designing questions for your love interest. One option is to use The 36 Questions, but those are geared to establishing intimacy. Today I’m interested in questions designed to find out if you and Mr. XO are compatible and whether he will make you happy.

My inspiration comes in part from a recent article in Fortune magazine that reported on challenging job interview questions. The out-of-the- box questions collected by the Five O’ Clock Club run the gamut from “How much should you charge to wash all of the windows in Seattle?” to “Describe the color yellow to somebody who’s blind.”

You can see where I’m going with this, can’t you? The wheels are turning. To keep us energized as we brainstorm, let’s have some broccoli quinoa salad with buttermilk dressing.

Some basic advice: don’t ask more than 1 or 2 of these questions per date and try to weave them into the conversation so you don’t arouse suspicion. And don’t ask them while strapping your date down and dripping a cup of water onto his face.

Questions to Ask Your Love Interest:

#1:

What did you have for dinner last night?

The correct answer: Baby kale salad with roasted apples and pomegranate seeds, bouillabaisse, home baked French bread, chocolate orange soufflé for dessert.

Relationship/compatibility subtext: You need a man who can hold his own in the kitchen – even if you’re an accomplished home chef. Not only will this make cooking together a viable fun activity or competition for you both (think Throwdown with Bobby Flay), he can comfort you with a home cooked meal when you are down.

#2:

If you had enough money to outsource one household chore, what would you pick?

The correct answer: Whatever chore you hate the most.

Relationship/compatibility subtext: The correct answer will show you whether he has listened to your complaints about your most detested household duty. It is important to find a partner who really listens and takes action to help you.

#3:

You go to the pound to pick out a puppy. The person in charge tells you they have a new pilot program. You may take home a new puppy every week for life or adopt one puppy,

The correct answer: Adopt one puppy.

Relationship/compatibility subtext: You want a one-woman man. 

#4:

You are on your way to work and running late to an important meeting. You encounter an adorable little puppy (O.K., I love puppies) who is obviously lost, confused, thirsty, and hungry. You know your significant other is making a presentation at work today, what do you do?

The correct answer: “I would take this puppy to work with me even if I was fired.”

Relationship/compatibility subtext: Depending on your age and life situation, Mr. XO’s answer provides clues as to whether he can sustain an egalitarian relationship. How would he juggle caring for your and his aging parents when you are both working? How might he handle parenting duties in a two-career household? What would Mr. XO do if you had a sick child, the babysitter had the plague, you were completing a crucial project at work and he had an important deadline to meet? Can this man step up to the plate and sacrifice his career if needed in support of your own?

#5:

You are stranded on an island with one other person who happens to be a woman. Thanks to a small island lake there is plenty of water but food is scarce. One afternoon, you are foraging for food by yourself when you unexpectedly encounter a plantain tree with one lone plantain on it. Do you eat it before you return or bring it back to camp to share?

The correct answer: Bring it back to share and offer the first bites to the woman.

Relationship/compatibility subtext: Mr. XO’s answer provides a clue to his generosity in the bedroom and whether he subscribes to the crucial philosophy of She Comes First.

#6:

Tell me about a time you had a conflict with a spouse or girlfriend. How was it resolved?

The correct answer: Apologize – regardless of the conflict or who is actually at fault.

Relationship/compatibility subtext: The simple act of apology demonstrates skills in conflict resolution and the reality-based truism that the woman is always right.

#7:

Why should I date you?

The correct answer: I have all the qualities you’re seeking according to your OkCupid profile and I think you are brilliant, beautiful, interesting, and everything I am looking for in a woman.

Relationship/compatibility subtext: Use your gut to determine his sincerity. Is the correct answer accompanied by gazing into your eyes? Is he a good kisser? Are you comfortable with Mr. XO and at the same time, do you have butterflies before you see him? The answer to this question must be weighed in the context of his entire package. No. Pun. Intended.

#8:

If you woke up and had 1,000 emails from matches on a dating site and could only answer 100, how would you choose which ones to respond to?

The correct answer: “Even though I could only answer 100, I would answer 5 and see what happens. If I find a good match, I don’t need to keep exploring and searching.”

Relationship/compatibility subtext: See above re: finding a one-woman man

#9:

What are 3 positive things an ex would say about you?

The correct answer: “She would say I was fun to be with, a great listener, and I was a terrific supporter of her and of women’s rights.”

Relationship/compatibility subtext: This is a perfect opportunity for your love interest to reimagine history. Most likely he will think back to a kinder, gentler time in a previous relationship and use his best spin technology to present himself in a good light. Use your woman’s intuition to determine if there’s even a shred of truth in his list of three.

#10:

You are on a road trip in unfamiliar territory and appear to be lost. The GPS is not working. What do you do?

The correct answer: Stop and ask for directions.

Relationship/compatibility subtext: Is Mr. XO a team player? Will he work with you to solve the problems of life or will he drive alone aimlessly while he runs out of gas and you run out of patience?

Can you add to my list of questions? Let me know! Until next week, happy dating or not dating.

XXXOOO

Nadia

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