Sneaky Ways To Ask Awkward Questions

Wondering why your date isn’t drinking or if the divorce is final? How to broach these touchy topics and others in an inoffensive way.

By Caitlin Ascolese

he dance of date-night conversation can be delicate. Small talk gets old, yet it’s hardly polite to pry into more personal topics, right? Well, here’s the thing: If you like a person, it’s those big questions that can tell you if he or she has real partner potential. And if there are red flags, wouldn’t it better to know sooner than later? “It’s smart to want to determine if there are any deal-breakers,” says communication expert Susan RoAne, author of How to Work a Room. Still, since it’s a turnoff to sound like you’re interrogating your date, we’ve found a collection of clever lines that gets you the same results as asking point-blank questions without making it look as if you’re doing detective work.

What you’re dying to know: “Do you have a life?”
How to ask it: “So what you have done lately for fun?”
Nobody hopes to be paired up with a hermit or a workaholic. Still, it can be hard to find out how your date spends his or her days without sounding like you’re judging…or
“Avoid questions that start with ‘Why’—they put people on the defensive.”
without getting a stock answer about what the person would do during down time if he or she could muster the energy. The solution? Ask dates to summarize a recent page from their daily planner—“So what were you up to last weekend?” works fine. You’ll get the real deal, says Alyssa Wodtke, author of Truth, Lies, and Online Dating. If your date draws a blank, then that could very well mean his or her life is a little, well, limited.

What you’re dying to know: “Are you serious about settling down?”
How to ask it: “What do you enjoy most and least about dating?”
What you really want to know is: Are you a player, or are you serious about finding someone? But those are big-time conversation-killers, so instead, find out what kind of attitude the person has about the single life. “You’ll get the info you’re looking for if you ask about the present,” says communication coach Laurie Puhn, J.D., author of Instant Persuasion. This question is also a decent substitute for that ultimate no-no: “Why’d your last relationship end?” You shouldn’t be bringing it up at all, but if you’re worried the person may be baggage-ridden, the circumstances of his or her last split will likely surface in response to this inquiry.

What you’re dying to know: “Why isn’t your divorce final?”
How to ask it: “So do you see your ex much?”
There’s a big difference between, “We’re still married on paper and living five states apart” and “We just broke up yesterday and still live in the same house.” It’s smart for you to want to know the status so you don’t get entrenched in someone else’s active divorce drama. “This tactic gets at where your date lives in relation to the ex without asking for details about the divorce,” says dating coach Nancy Slotnick, author of Turn Your Cablight On. How your date answers — both the info the person shares and the tone he or she uses — will tell you everything you need to know.

What you’re dying to know: “Why aren’t you working?”
How to ask it: “What are the career goals you’re working on now?”
In today’s economy, it’s normal to meet people who are freelance, between careers, or freshly laid-off. But what if this person is what you fear—just not the kind to hold down a job…ever? The way to separate the slackers from those in transition is to “focus on the future and imply that the person is moving forward,” says dating coach Denise Budden-Potts, Ph. D., founder of “Dating With Your Future in Mind” seminars. “Avoid questions that start with ‘Why,’ as that word makes people feel immediately defensive.”

What you’re dying to know: “Do you want to get married someday/have kids?”
How to ask it: “I think there’s an epidemic going around—all of those celebrities who are getting married/pregnant!”
This is a biggie—if you and your date have differing ideals about holy matrimony or
Avoid questions that start with ‘Why.’
future family size, there’s not much point in carrying on together. Still, asking this question all but screams you’re putting the cart before horse. That’s why phrasing it as if you think there’s something in the water can work so well. “It becomes a conversation, and you’ll be able to tell how a person feels by how he or she responds—whether it’s cooing or changing the subject,” says life coach Lynn Rasmussen, author of Men Are Easy.

What you’re dying to know: “Why aren’t you drinking?”
How to ask it: “I noticed you ordered juice. Do you mind my asking if that’s a policy—or just a preference tonight?”
Keep your query sounding curious, not concerned, and you’re likely to get an honest answer. “If someone doesn’t drink across the board, it could affect the way you two date if you’re a social drinker,” says author Susan RoAne. It may just be that the person doesn’t booze when he or she has spinning class the next morning, or you may find out that your date is in a serious recovery program. Either way, this approach lets you broach the topic in a non-judgmental way.

What you’re dying to know: “Do you rent or own?”
How to ask it: “What made you choose this neighborhood?”
You may be genuinely curious, but it’s hard to pull off this question without seeming like a gold-digger (even if you’re a guy). “Asking about someone’s financial situation puts them on the defensive,” says Slotnick. “Framing it as a question about the neighborhood can tell you about his or her personality and lifestyle.” And in telling the story of moving in, most people will mention either the process of purchasing a place or the role rent prices played.

What you’re dying to know: “Do you have a lot of friends?”
How to ask it: “Where did you meet your closest friends? What do you do when you get together?”
Many super-social single types can’t imagine settling down with a more solitary soul—and vice-versa. Here’s how to find out just which end of the spectrum a person is on: “Focus on the positive and assume the person has a social network,” says RoAne. “If it comes out that he or she says there’s no time for friends, then that’s what you need to know.” Another good solution is to ask where he or she met his or her closest buds—if it’s a mix of folks from grade school through current cubemates, you know you’ve got a likable, loyal type on hand; if it turns out that most of his or her “friends” are really co-workers who have to spend time together, you can take that under consideration. If a person describes a wide array of casual friends who hang out at the same club, you’ve just gotten a good clue about what makes this person tick; if your date has two best friends from his or her house of worship, that reveals a lot of valuable information, too.

Caitlin Ascolese is a freelance writer in New York City.
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