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?
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.
About the experts
Amy Spencer is the author of Meeting Your Half-Orange: An Utterly Upbeat Guide to Using Dating Optimism to Find Your Perfect Match.
Therapists Michelle Fiordaliso and Heather Belle co-wrote the book Everything You Always Wanted to Know About Ex*.