What To Ask To Really Get To Know Your Date

Even though there's much more to us than our professions and lots of people don't define themselves by their jobs at all, many of us still begin date conversations with "What do you do?" because we're at a loss for questions to ask on first dates. Some singles, particularly men, have even told me "What do you do?" puts pressure on them, as if they need to answer with something that indicates wealth or social status.

I can see how someone might ask that question with hints of classism, but for me, it has always been a way to say, "How do you spend your time?" or "What are you passionate about?" So, it recently occurred to me: Why don't I just ask people how they spend their time or what they're passionate about? Wouldn't that be a more direct way to learn about them? For me, that's the same as my profession, but for many, it's not — and if that's the case, I'd rather hear what keeps them up at night than what keeps them at a desk from nine to five.

Here are a few questions you can ask on a first date if you truly want to understand a romantic prospect, because I think we're all tired of wasting our time on interview-like dates and small talk.

To Break The Ice, Try...

1. "Do You Live With Anyone?"

No matter what the answer, this question invites follow-up questions. Maybe they like their roommates now but their last roommate situation was a disaster, and you can chime in with your own roommate horror stories. Perhaps they've recently moved back in with their parents, which provides the opportunity to ask about their family relationships and hear about their upbringing. Or, it's possible they live with a cat, which lets you ask for pictures. And if they live alone, that's also a chance to go deeper: Do they get lonely? Afraid of the dark? Or do they just love using the bathroom with the door open? (OK, maybe that last question isn't initial break-the-ice material.)

2. "What Neighborhood Do You Live In? How Do You Like It?"

Once you know what someone's living situation is like, you can ask where they live geographically. Presumably, you reside in the same city, so that city is a built-in talking point. The question of how they like their neighborhood also opens up a can of worms: Did they like their last neighborhood better? Do they ever go to that cafe near them that you love? Does the train line they're near drive them as crazy as you?

3. "What Did You Study In College?"

We all love to act like know-it-alls once in a while. If you know something about your date's field, ask them for an expert's take on it. Or if you know nothing, ask them about the most interesting thing they learned. You can also ask if they apply their knowledge to their daily lives now, even if their profession seems unrelated, or for their take on a relevant current event. Even if they hated their major and chose it due to pressure from their parents, that's a topic of conversation itself. These questions can all get you beyond small talk if you ask them the right way.

To Peel Back The Layers, Try...

1. "Do You Have Siblings?"

Obviously, you don't stop at "yes" or "no." If they answer "no," you ask what it's like to be an only child. If they answer "yes," you ask if they're close with their siblings. They might have some funny or revealing stories about them. Then, the opportunity is ripe to ask if they're close with their parents. See how this works?

2. "Do You See Yourself Living Here Long-Term?"

This not only tells you about your date but also might provide insights into your long-term compatibility. Are they aching to get out of the city like you, or do they love the hustle and bustle? Do they see themselves starting a family in the suburbs, or does the phrase "settle down" fill them with dread? These are valuable things to know when evaluating a potential partner.

3. "Do You Like Your Job?"

OK, so it does help to ask "What do you do?" at some point. But in my experience, that'll come up anyway as you ask more substantive questions, if you don't already know from their online dating profile. Rather than simply finding out what someone does on a day-to-day basis, this question will tell you what does and does not interest them and what their dreams are for the future. If they don't like their job, find out what they'd rather do if there were no practical considerations. It's fun to share what our wildest fantasies are.

4. "Did You Predict You'd End Up Doing What You're Doing?"

Here's another work-related question that goes deeper than "What do you do?" Asking your date if they pictured themselves where they are now prompts them to talk about how they got there, which for many is a long and winding road full of interesting stories.

To Get Really Deep, Try...

1. "What's Something You've Been Struggling With Lately?"

I know — this one isn't conventional, and you may have to get pretty comfortable with a person before you ask it. But a very unconventional person asked me this on a first date once, and I loved it. It was an invitation to confide in him, and we all want someone to confide in. Besides, who are we if we can't talk about our struggles? We aren't human if we don't have struggles, but too often, first dates provide pressure to pretend we don't. When you ask someone this question, you're conveying that it's OK to be real. Just make sure you've reached the point where they'll feel comfortable answering.

2. "How Long Have You Been Using [Dating Site]?"

This question introduces the elephant in the room and also opens the door to a more human side of you both. If you met on a dating site, you can probably commiserate about a lot of common online dating experiences. This might sound potentially uncomfortable, but it doesn't have to if you limit the discussion to the past. It might even present the opportunity to laugh about first-date horror stories. Or, if you want to get really deep, you can steer it toward a discussion of past relationships. I've found that acknowledging you met on a dating site breaks a lot of tension because you no longer feel like you have to hide your situation. It may even lead you both to admit how nervous or happy or ambivalent you are about the date taking place, which is always informative.

3. "What's The Biggest Challenge You've Overcome?"

Something important to me in a partner is that they've overcome adversity. I have, and I don't think someone who hasn't would really get me. The capacity to surmount hardship also shows strength of character and ability to tackle the obstacles life throws at couples. Talking about the challenges you've overcome will force you to let your guards down and become closer. Like the other deep questions, this one might not be ready to come out until you're really connecting, possibly on a subsequent date, but it'll pay off.

Small talk may seem safer than all these conversations, but it also can be boring and doesn't always tell you what you need to know about a potential mate. Plus, what would you rather know: the last time someone cried or their favorite color? Even if a first date doesn't lead to anything, at least it'll provide a good time if you discuss something interesting. You might even come home with a new perspective on life, and that's worth breaking out of your comfort zone.

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