9 Questions To Ask On The First Date
Want to learn everything you can about your new gal – or even your lifelong partner? Start by slipping in these questions between appetizers and entrees

January 1, 2013

man and woman sitting at a dinner table looking into each other's eyes

You’ve spent some time with her bantering loosely about the usual stuff – restaurants, television shows, her pinterest page – and now it’s time to start finding out what really makes this woman tick. Why waste time with the usual conversational pink slime? Start by slipping in these questions between appetizers and entrees and dig deep!

The trick is to tap – the same tools psychologists use to gauge personality. Some shrinks shoot for a roster of telltale traits called the big five – extroversion, openness to new experience, agreeableness, conscientiousness, and neuroticism. “Those traits often become problematic at their extreme ends – when introversion, for example, becomes detachment,” says psychologist Dr John Mayer, of the University of New Hampshire.

Related: Five Date Ideas That Are Better Than Dinner

Other experts believe you can scoot by with fewer levels of inquiry. “Traits give you the broad strokes,” says Dr Dan McAdams, a psychologist at Northwestern University. Instead, zero in on her motivations and try to discover how she see’s her life’s narrative.

We developed nine threads you can drop in here and there to either skim the surface of her psyche or go in deep. Bonus: they can work at any stage of a relationship, not just the first date. So relax if you don’t get through all of them on the first date, maybe try one or two. After all, you never want to stop learning things about the woman you’re with, right?

Tell-All Question #1:

Want to dance on top of this bar with my friend Kylie?

Okay, that’s a bit forward. Instead, just ask her straight out: “Do you like this place?” As traits go, extroversion is hard to miss: a big smile, an easy posture, and lots of eye contact all signal an outgoing personality. But if the tell-tale signs are fuzzy, this question can help you figure out if she’s a wallflower or a party animal, says Dr Bernardo Carducci, of Indiana University Southeast’s Shyness Research Institute.

Related: 12 Signs Your Date Is Not Going Well

If she’s an introvert but you sense that she wants to change that, plan dates that allow for mingling with strangers, suggests psychologist Dr Seth Meyers, such as wine tasting or a cooking class. “If she’s on the shy side, she’ll be more likely to come out of her shell if you take the plunge and engage others first,” he says.

Tell-All Question #2:

How about some poison fish?

Dinner is a great chance to gauge her openness to new experiences. Hit her up with “Like to share a fugu shashimi? Apparently it’s deadly if not properly prepared!” If the idea of such novelty has her scanning for the exit, you won’t be bringing her to a wild party at AfrikaBurn. Still, you don’t have to turn the outing into a Fear Factor audition just to find out if she’s adventurous.

Ask her which movies, music, books, and art she likes. “The real tell is variety,” says Dr Sam Gosling, a psychologist at the University Texas at Austin and the author of Snoop: What Your Stuff Says About You. “Twenty books on 20 subjects suggest more openness than 200 books on one or two subjects.”

Related: 8 Things You Say On First Dates That Guarantee You Won’t Get a Second

If she doesn’t seem adventurous, boost the PDA factor, suggest dating mavens Emma Taylor and Lorelei Sharkey, of emandlo.com. A kiss on the sidewalk, a sly butt-pinch in the grocery store (but only if she has given consent, don’t go harassing women) – these encourage adventurousness.

Tell-All Question #3:

Want to move to Namibia with me? Today?!?

Don’t let her hotness blind you from facing facts that might result in a hot mess. “In context, ask her how she’s made important life decisions, such as accepting a job or making a move,” says psychologist Dr Craig Malkin. “You’re looking for signs of a reckless, flaky approach to life.”

If she’s thoughtful and reflective, he says, chances are she’s high in conscientiousness – a trait that suggests she won’t be flaky with you. Or ask her advice on dealing with a colleague of yours whose work has become sloppy. “You’ll see the standards she holds herself to,” says Rita Watson, a relationship columnist with Psychology Today.

Tell-All Question #4:

Any ex-boyfriends you’d like to punch?

If you have a chance to ask her about her relationships with old friends, former mates, or family members, jump on it. Her answers could provide a valuable window into her agreeableness. “People who score highly in this area tend to be forgiving of the wrongs they’ve suffered, lenient in their judgement of others, and willing to compromise,” Mayer says.

Related: He Ex Boyfriend Might Be The Greatest Threat To Your Relationship

If mentions of exes are slathered with acrimonious sentiment, it could be a sign that she holds a grudge or lacks much empathy. You really don’t need that.

Tell-All Question #5:

Here’s R10-million. Would you quit your job?

If you ask her if she likes her job and end up listening to an hour monologue about why her nine-to-five sucks, she might be a bit neurotic. People high in neuroticism often have turmoil in their lives, Malkin says. “They tend to be more unhappy, and so are their partners,” he says.

Also, take notice of her usage of the word “I,” which can be a red flag if it’s excessive, says psychologist Dr James Pennebaker, of the University of Texas at Austin. “When people are anxious, they look inward,” he says. “People who are low in neuroticism are not paying attention to self.

Related: How What You Say on a Date Makes You More Attractive

They’re looking outward, focusing on the environment or other people.” To see if she can change tracks, try a gentle nudge, says Malkin: “I hope our date’s a break from all that – a chance for you to enjoy yourself.” If she’s capable of shifting gears, she’ll take the hint and possibly even acknowledge being so wrapped up in her worries.

Tell-All Question #6:

What gets you out of bed in the morning?

You’re digging deeper now, learning about her personal ambitions – what she’s passionate about. “You want to see if she’s striving to accomplish things over time and can express herself through strategies, plans, and values,” McAdams says.

Related: 5 Signs You Could Be A Boring Person

This is where you really start to know her. What her passion is can be a valuable bit of intel, giving you insight into how she views the world. If she looks at you blankly, what you infer may be just as valuable.

Tell-All Question #7:

How would you launch your dream career?

Is she a procrastinator? A daydreamer? A go-getter? How she sets her career goals and charts a course to realising them can also indicate how she achieves goals in other areas of life, including her relationships. Dr Ann Demarais says you can build up a picture by noting the specific goals themselves.

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“Say she wants to write a novel,” she says. “She’s telling you that she’s creative and interested in people’s motivations and that she has something to say about the world. If she wants to start a business, that desire could signal independence, drive, perhaps a capacity for taking on risk and shouldering responsibility.”

Tell-All Question #8:

What was the most significant turning point you’ve experienced personally?

For years McAdams has been learning about people by asking them to tell him their life stories. They share the highs, lows, and turning points and establish overarching themes. “We’re all autobiographical authors,” he says.

Related: The One Time It’s OK to Ghost On a Hookup

“We make our lives into stories that we them tell ourselves to give our lives meaning and purpose.” If she says she loved growing up in a small town but yearned to live in a major city, she’s creating a narrative that lets you know her past, present, and future are connected. Eye-opening, isn’t it? Maybe you should ask yourself the same question.

Tell-All Question #9:

What hurdles have you overcome in your life?

The way people explain events says a lot about them, Malkin says. “Is she always the victim? Does someone or something always spoil her plans? If she regularly attribute misfortune to events beyond her control, you might be hanging with a narcissist,” he says.

On the other hand, blaming herself for every problem could be a sign of poor self-image, Malkin adds. “Research suggests that people who are frequently down on themselves are often down on their partners too,” he says.

Related: Ready To Call It Quits? This Is How You should Break Up With Her

Worried you’re with a narcissist? Ask her if there’s a choice she regrets. A resilient woman can talk about her mistakes. A narcissist will dodge the question by placing blame again. If you think she’s esteem-challenged, try a little cheerleading: “Sounds like you did the best you could under the circumstances.” If she can’t be kind to herself at all, Malkin says, she’ll accept your support and drop the self-recriminations.