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15 questions we’d love to ask our new dates…but are afraid to We don't want to risk appearing rude, nosy, or outright crazy—but this is what is on our mind when we first meet someone.

When it comes to the very beginning of a relationship there are some questions that are just off-limits. To ask them is to risk appearing rude, nosy or outright crazy.

But what if you could ask anything during those first few getting-to-know-you dates without the threat of scaring away your brand new man? A little knowledge could prevent headaches and heartbreak later.

I presented this hypothetical to relationship and dating experts Amy Spencer, Michelle Fiordaliso and Heather Belle, and polled regular women for their thoughts. Here are their juiciest queries, both silly and serious.

(And guys who are reading this for some reason: consider linking this article to a new or prospective date and offer to fill out the answers. She’ll appreciate it!)

#1. Were you disappointed or excited when you first saw me?

Then again, it might be worth it…

The answer to this question could indicate where your relationship is headed, say Michelle and Heather, because there is a saying that women become more attracted to the men they fall in love with, but men fall in love with the women they’re attracted to.

#2. Are you mentally unstable? (Alternative phrasing: Is anyone in your family koo-koo for cocoa puffs?)

It would be nice to know if you’re dating the next Jeffrey Dahmer before it’s too late.

#3. Do you share food?

If a guy doesn’t want to share a bite of his chicken parmigiana with you, he may not be generous in other areas of your relationship, says Amy. The same goes for guys who don’t tip well.

#4. How many pairs of shoes do you own, and which pair do you wear the most?

“This would tell you pretty quickly where he lands on the grooming-maintenance scale,” says Amy. “And the pair he lives in would tell you if he’s, say, an Italian moccasin, Polo grounds-visiting type or a Vans-wearing, skateboard-loving, laid-back kind of guy.”

#5. How often do you think you’d be giving me massages?

“If he says, ‘Pfft, yeah right’,” says Amy, “you can be pretty certain he won’t be rubbing your shoulders and playing with your hair any time soon.”

#6. Are you doing your dream job — and do you care?

Men who don’t identify with the work they do could end up depressed on a daily basis, say Michelle and Heather. And if he doesn’t seem interested in finding a job he would like, then do you want to be with someone who has such low standards?

#7. How many girls have you hooked up with this year?

“If he’s already hooked up with a double-decker busload, you can decide whether you want to be another one,” says Amy.

#8. Does anyone else think they’re dating you right now?

People tend to ask if their date is seeing anyone else, but according to Michelle and Heather the answer might not be the whole truth. In other words, your guy may think he is not dating anyone else, but the woman he slept with last Saturday night may think otherwise.

#9. What’s the most common thing you’ve heard when girls see you naked for the first time?

If the most common reaction is “Wow!”, you’re in for a real treat, says Amy. On the other hand, an “Oh …” may at least prepare you for a little disappointment.

#10. Why did your last relationship really end?

This will come up eventually, but you want the unedited version of the story. “It’s a bad sign if he says his ex hated how much he flirted,” says Amy.

#11. How many exes are you still in touch with?

You don’t necessarily want him to say they’re all his best friends but, says Amy, “if he cuts off all ties and runs for the hills after every breakup, what the heck’s going so wrong?”

#12. How do you fight?

Everyone gets angry at some point in the relationship, say Michelle and Heather, but it could save you a lot of trouble to know what type of behavior to expect in the future.

#13. When I say the word “marriage,” what do you think?

Does he gulp, cringe, laugh? “This is a great way to see where your date is at on the ready-for-a-relationship scale,” says Amy.

#14. What percentage of the time do you think your pee actually hits the toilet water?

If a guy doesn’t care enough to aim straight, says Amy, then you’ve really got to wonder how clean he is in other areas of his life.

#15. How soon would you be open to kids, and do you even want children?

“Most women don’t ask about this for months or years but if it’s really important to you, it would be nice to know from the get-go,” says Amy.

***

Also check out 37 things everyone should be legally obligated to disclose before the first date.

Sorry, Afrunauts! We can't allow comments until we have built an ethical way to address the troll problem.

9 thoughts on “<span class="entry-title-primary">15 questions we’d love to ask our new dates…but are afraid to</span> <span class="entry-subtitle">We don't want to risk appearing rude, nosy, or outright crazy—but this is what is on our mind when we first meet someone.</span>”

  1. The massage question is the most important , Thats the one that would define who is going to give a damn about me in 40 years from now, who is going to really care about me when i get home from work that i love oh so much, who is a far more caring partner than all the exes that i still occasionally say hello to, etc. A woman with that much sensitivity to my needs is the one to tame this savage beast.

  2. Here’s what I would ask a woman:
    1. Would you sacrifice convenience to be with someone you loved? A lot of people in America are selfish and lazy, so this is important to me.
    2. Are you financially stable? Do you do drugs? Smoke? Alcohol? I actually prefer not do to any of these, except alcohol just to be social.
    3. Are you compassionate? How do you treat the least among your colleagues? After infatuation goes away, that’s how I expect you will treat me.
    4. How many relationships have you been in? Some girls, especially pretty girls, go through many relationships and are a poor prospect because they think guys will do anything they want. Which doesn’t make for a relationship. Hookups I wouldn’t mind as much, though someone who has cheated I would be wary of.
    5. Where are you going with your life? People are happy when they have meaningful work. This could be a career, or a mission, anything that gives them purpose and passion.
    6. Do you like massages? I love giving and receiving massages :-).

  3. i talked about or asked pretty much all of these questions with my current boyfriend the first night we met. our 8 year anniversary is in october. sometimes it’s nice to just cut the bullshit and see if you’re on the same page.

  4. If I was on a date and anyone asked me anything similar to these questions, I would run outta there like a bat outta hell. It tells me you are insecure and need constant reassurance. How about some sincere questions?? About what people are about not how many shoes they have in their closet or how many people you slept with (which I would never answer even in extreme tourture situations) EPIC FAIL!!!!!

    • These would be pretty scary questions to hear on a first date, but as the intro says, these are questions that women would LIKE to ask if they could. Nobody’s suggesting that they do it, so no need to be so alarmed.

  5. I do this. I have a relatively large-mesh brain-mouth filter (a lot of stuff gets through, I’ve been described as “brutally honest” on more than one occasion) but I don’t understand why we can’t just be honest. The first date is about getting to know one another and deciding whether or not you want to continue seeing that person, i.e. finding out where that person stands on a relationship-commitment level. If you’re serious about finding someone to have a life with, why not ask these questions on a first date, be honest and give him/her, and find out if you want to continue seeing this person. I’m convinced this would save some people a lot of trouble. Plus it would make for more interesting conversation than family, weather, and news. But I have one question – these are questions that women want to ask men. What questions do men want to ask women???

  6. Little bit of advice, all those questions are fine and dandy and would actually be interesting topics of conversation. EXCEPT #15!!! You ask that on a first date and you might as well just get up and leave. Even if the guy is ready for kids relatively quickly, that’s till a no-go topic for a first date. This website needs some guys on the staff. Whoa….

  7. Talk about hypothetical.

    “How often do you think you’d be giving me massages? ”

    Every weekend. That’s what he said when we started dating. I think you can guess how many massages I got after that.

  8. Im a guy and pretty laid back, and can honestly say I wouldnt care if they asked me these questions. Id be honest too. If they didnt like what they heard, Id wanna know about it too

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