Questions We Wish Were Appropriate To Ask On A First Date

Dating is like those blow pops with the question marks on the wrapper: You just never know what you're going to be putting in your mouth. Sometimes it's very good! And sometimes, alas, it's just not your flavor. For example, you might wake up in someone's house after your first sleep over and stumble into their kitchen thinking that you just met a cleaning lady while getting a glass of water. Then it might turn out that the cleaner wasn't actually a cleaner but was, in fact, their mom with whom they still live with at 35. And scene. But wouldn't it be great if you could minimize these bad surprises by asking all the questions you wish were appropriate to ask on a first date, but clearly aren't because it would make you look like a nutjob?

Questions like:

Do you have any extreme (or even moderately extreme) sexual perversions?

There are very few things that I can't roll with. If this is a mild case of being addicted to sexting, it probably won't be an issue. I might even be excited about it. However, if you are going to be unable to be sexually satisfied fully unless I'm willing to sit down on a three tiered cake naked with you, that's something I am going to want to know RIGHT NOW. I know first date may seem too soon to say something like, "Hey do you want to split an appetizer? By the way if we get serious I'm going to want to dress up like a pony and have you ride me around the house." Guess what? It's never too soon to bring those things up.

Have you ever set bugs on fire?

I don't want to play So I Married An Axe Murder. If you are some kind of creep with violent tendencies then tell me now. I don't want to find out later that the cat keeps running away from you because you have been punting it across the room when I wasn't looking, simply for shedding on your suit jacket. So yes, I worry that your morbid childhood curiosity could be a warning sign; you'll certainly have to explain yourself.

When is the last time you cried?

If it was longer than a year ago, I have concerns. It means you might have a medical problem or you might have accidentally left your feelings back in 1994. (Or it could mean that you've had an incredibly awesome and upbeat year, I suppose.) Most people who are self-aware enough to recognize their own difficult emotions will, at some point, shed a tear or two. I probably do it a little more than most. I'm not saying you need to be sitting next to me holding my hand and crying during the finale of American Idol, but I would like you to be able to squeeze a few out if something really emotionally intense happens. Just so I know you are still in there.

Do you have children and/or a psychotic ex?

I once made the mistake of PICing (playing it cool) on this one too long; I woke up in the guy's bed for the first time only to discover I was sharing it with a child's toy. His child's toy. Because that's an easy thing to forget to mention, that you have a child. I also think it's important because I disagree with the Millionaire Matchmaker who claims that divorced men are gems. Some might be, but many of them have to recover from the minor (and/or major) PTSD induced by the experience before they can get back into functional human being dating shape.

Can you read? Do you read?

Contrary to what a slew of infographics would have us believe — namely that people can no longer understand information that isn't presented in pictures — some people still read. On paper, even. I am one of those people. I can't spend a lot of time with someone who can't read because when we are on planes, trains and traveling in general, you will be sitting there staring at me while I am reading and I will want to throw my book at your head in the hopes that some information will be absorbed through osmosis.

Have you heard of the Arab Spring?

I'm going to need you to have a fairly decent grasp of current events. It would be good if prom queen/king wasn't the last thing you voted for. Some information about geography is also a bonus. Do you know where you are? Do you know where Sudan is? I'm not saying you should have the topography of Turkmenistan memorized, be able to list off every US senator and pepper your conversations with allusions to Supreme Court cases. I just want to make sure that we are living on the same planet, and that on that planet there is some shared sense of political/social awareness and civic responsibility (this coincidentally includes putting the seat down so I don't go swimming in the toilet in the middle of the night).

Are you going to try and win at every game? Even, for example, when playing badminton with your future children?

Are you the type of guy who can't even let a five-year-old beat him in Go Fish? Will you run around the lawn screaming with delight when you beat my 65 year-old-father at bocce? Are you going to challenge my sister to an arm-wrestling contest? (If you knew my sister that would make more sense). Everyone likes a winner, but even more I like people who understand how to pick their battles. Sometimes letting someone else come first in the game makes you a winner. Be a winner.

Do you have a savings account?

No, your change jar doesn't count. It's not that you already have to have the perfect 401K plan picked out and be able to afford a down payment on two houses. I don't give a shit about your income. I just want to know that you try to at least occasionally put some money away for whatever fun stuff and/or emergencies the future may bring — or maybe, at some point down a long road, to support the expenses associated with a small mammal, like a dog or a child. Being able to put some money away — even if it's $25 when you can — shows that that you have a little maturity and self-restraint, two very sexy qualities past the age of 25.

In this fantasy first-date interrogation, we've probably hit the coffee/dessert course and your eyes are rolling around in the back of your head. Or I have just learned that you love a Cleveland Steamer, the last book you read was in junior high and written by R.L Stine, and you think the President has "Bush" somewhere in his name. Which would be quite unfortunate, but at least I'd know to awkwardly look at my watch and feign surprise at the time and oh, gee, I have to get up early tomorrow and let's go Dutch.


Sarah lives in NYC and her life is currently a series of great meals, questionable decisions and bizarre first dates. Follow her on Twitter: @sarahh314.