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If she says "my job" I know that work is super important to her. Best one I've gotten back: "Not nearly recently enough! I don't care if it's "jogging" or "skateboarding" or "powerlifting," (well, I care if it's powerlifting), I just want to know she's into fitness.__First dance song you'd put on a mix tape? It's also a great way to read a person: the music they would give to someone else. What questions would you ask someone you were messaging online? More on Dating at Glamour.com25 First-Date Dos and Don'ts"How We Met" Stories: Do You Love Yours?

Have a question about Dating, Relationships, or Sex for Single John? Dating Long Distance: Should I Take a Risk and Tell Him I Want More?

It can be hard to figure out what to ask without making it seem like you're interrogating your date.

After all, the key to a good date is relaxed conversation, and the last thing you want is to recreate the beginning of this scene from But whether you're trying to fill an awkward silence or just trying to get to know your date better, we have you covered.

He asked her a silly question and started grilling her with more and more trivia questions, teasing her about what she might win if she got all the questions right. “It made me funny in response to him,” she replied. They’re just as boring as the ones that you received.

She played along and pushed right back and they’ve already got a first date lined up. “He was so lively and engaging that I sort of had no choice but to come back with something equally witty and creative.” “So by him writing something playful and interesting to you, he actually brought out a more playful and interesting side of you? Wouldn’t it stand to reason that if you took the time to write something interesting and creative back to these guys, you might discover that they actually have a personality?

And yet this one guy with the trivia questions was able to bring out your playful side.” The moral of the story is that you are ALWAYS responsible for how you leave a conversation. By being optimistic, playful, interested and interesting, you can almost always transform any evening into a pleasant experience.

Obviously I'm not so cheesy as to ask the same questions of everyone. Allows me to figure out, if we ever dated to the point of sleepovers, whether she'd want to get up and go jogging at 9 A. I could write an answer to this question that would last pages and pages. This question is less of a test than pure curiosity at work. If she says "the water" she may be into surfing or kayaking or a similar sexy sport. I'm not a secret social worker compiling stats on abused children.

M., or whether we could roll around in bed, maybe watch a movie and waste half the day (guess which one I prefer).__What's your choice for a last meal (before execution)? I want to hear how important food is to her, and how creative her tastes are. I'm, frankly speaking, an amazing cook, and I want to know what's she's bringing to the table (also helps me weed out the vegetarians, without having to ask; I'm fine with vegetarians, but it's like a religion, I prefer to know early). If she says "my vacation house in Bali" I know she's probably got money and spends time on exotic islands. I am deeply suspicious of people who are OK with them. This cheeky question is posed to see if she's down with a little sauciness, and how funny or creative she can be with her naughty answer. I'm an active fellow, and I like to know that people I'm interested in are as well. And while I'm not too much of a snob about it, I need to know what she's going to make me listen to.

Also, if anything out of the ordinary has happened that might be affecting your date’s mood, it’s good to factor this in. Also, it’s nice to give your date an opportunity to answer a question that isn't directly about them.

On a first date go for a friendly tone rather than an intimate tone when asking this question. Don’t be afraid to change plans if you arrive at a restaurant and find it’s too noisy for a good conversation.




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