15 Intimate Questions That Are Not Asked Often Enough

There are a lot of questions out there that we are dying to know the answer to. Whether it’s out of fear from knowing the answer or risk of embarrassment, we hold back and pray that the answer will come to us by way of another method. Maybe someone will mention it by chance, or you’ll discover documents or trinkets that will hold the answers you seek. If we can avoid asking, we’ll feel better in the moment, but it won’t keep the question from weighing on our chests.

While there are some questions that don’t hold the level of intimacy as some, such as “Want to have dinner together?” or “What’s your opinion on cheese? And brie honest.”, there are other questions that need to be asked between partners, co-workers, and people you hire. It’s not always easy, but learning a little personal information about someone could protect you from a lot of future damage.

The trickiest part of asking these questions is to find out the right way to approach it. Do I just come right out with it? Set the mood? Also, you have to be prepared for whatever answer you get; another scary thing. Just blurt it if you have to and laugh about the approach later. Whatever. Just get ‘er done.

15. Are You A Virgin?

With the way young kids talk and act nowadays, it’s surprising to learn that North American “kids” are getting into sensual antics waaaaay before we ever were. At the same age that we were still receiving stuffed animals as presents, they were losing their virginity. Cut to our adult life, where we can now virtually Dial-A-Romp at the swipe of our finger, it’s easy to assume that the term virgin is reserved for those who haven’t yet hit puberty. But you know what happens to those people who assume? While getting busy has become second nature to some, it’s not always the case. Asking this question may get a laugh from certain people, but it could also be the four words that help make someone’s first time, or general lack of experience, more enjoyable or at the very least, something to think about before jumping into.

14. Are You A Smoker?

Smoking is not as common as it was fifty years ago. When every Tom and Sally were lighting up their Lucky Strikes, their children were catching sight of this habit and inhaling the secondhand fumes. These children later adopted this habit in adulthood and learned the unfortunate effects of their nicotine addiction: gingivitis, lung cancer, stroke, and death. Now, smoking is banned from many places and less people are taking to the tobacky. If you’re a smoker nowadays, it’s taboo and unattractive to any would-be partners. It used to be sexy. NOT NO MO. Many try to hide their nasty habit with gum, mouthwash, mints, sprays, and excuses of “needing to get some air”. Suspicious of their minty-fresh breath or not, if you’re not okay with the smoker life, it’s a question you should be asking.

13. Have You Ever Been Arrested / To Jail? What For?

Diving deep into someone’s personal life is tricky for anyone to do. After all, who is ever up front about the past, especially if it’s a past they’d like to forget? Asking this question is important if you’re dating someone, but also if you’re hiring an employee, babysitter, or are trusting someone to manage your assets. Wouldn’t you want to know if your fiancée had been locked up? Okay, maybe you don’t want to know the answer. If they say yes, sit down and prepare for their story. It may not be as bad as you’re suspecting. Peeing in public? Meh. No big deal. But maybe you’ll learn of their pedophilia conviction and will need to rethink your plan to have six children together.

12. Are You Married?

This question may not seem like one that is pressing, but you truly never know what kind of life someone leads. Remember the Ashley Madison debacle? The amount of spouses seeking comfort in others was astounding! Especially if you’re in your thirties, asking this question is becoming a less far-fetched idea. If you’re seeing someone new and it’s starting to look promising, it’s best to pop open a bottle of wine and sit down for some real talk. If someone is married, it’s not very likely that they’ll be honest about it (since it’s obvious they’re trying to keep this fact a secret). Even so, you may be able to discover that they’re separated, divorced, or are a widow/widower; little facts that are also worth knowing.

11. Have You Ever Cheated On A Previous Partner?

Ever hear the phrase, “Once a cheater, always a cheater”? This common BFF response to the naïve consideration of returning to a cheating partner is often the winning argument. Sometimes people change, and sometimes partners only stray once. But just like the haters gonna hate, it’s true that more often than not, cheaters gonna cheat. Learning about the potential that your blooming romance is facing may change your perspective of your new love. It may be hard news to hear, but trust, it would be harder to learn when it’s too late and the delivery of information is much more hurtful. Asking may also come with ulterior motives: Can I hold this against them? Have we both cheated before and wish to reform with each other? Aww. Cheaters gonna cheat (with other cheaters).

10. How Many People Have You Slept With?

Being intimate with more than a handful of partners can be a red flag for some people. For others, it can be a turn on to know that their new partner had a pretty scandalous past. To know that their raunchy history has resulted in them dating you (exclusively!) might fill you with pride to have landed such a stud! It might also result in you asking them to get tested for STI’s or have you secretly wondering if they were an unknowing donor for a Boyfriend Jr. Either way, whatever answer you get from asking this question will open them up for a little judgement, so be prepared for an answer that may be slightly skewed. Is the number too little? Too high? They may adjust the numbers to reflect what they think you want to hear.

9. Do You Believe In Monogamy?

There are usually only two reasons someone might ask their partner this question: They are looking for a monogamous partner, or they want to know if their partner is okay with being polygamous. Most of the time people are just wondering, “Will I be enough for you?”. However, some ask because they wonder, “Will they be cool with me sleeping with other people?” Whichever direction you or your partner swing in, it’s helpful to know which side of that door you’re both going to be on. Partners set their own rules all the time when it comes to the type of relationship they want to have and are comfortable with. But in order to establish those guidelines for the two of you, you have to learn the answers to these questions.

8. Do You Have Any Debt?

For your bank representative, insurance broker, or realtor, it may not be that difficult for them to ask this question. Yes, it’s personal, but it’s also in their interest to know. Another person with an interest in this answer is any future spouse. If you’re about to officially partner up with another, marrying into everything from their flaws to their assets, it’s ideal to know about any trouble you could be taking on as a result. If your partner is paying off their student loans and car, that’s one thing. But if they’ve racked up four or five hundred grand in credit card bills, you’ll have to consider, “Is this something I want to share responsibility for?” If it’s something they’re struggling with, maybe the two of you can figure it out, or maybe it’s best to let them drown in it.

7. Do You Suffer From Anxiety, Depression, Etc.?

Mental health issues, such as anxiety and depression, are serious weights that many people carry around with them on a daily basis. As a society, we’re opening up to the fact that a lot of people suffer in silence from these issues. Overall, we’re learning to accept them and learn how to cope and help. If you’re in relationship, it’s good to know about this so that you are able to handle certain situations more delicately and extend your partner a little more patience. Being aware of their struggles will bring more understanding to the relationship. Even potential employers shouldn’t be afraid to ask this question. If your coworker or employee is a little late to turn something in or you notice they’re less focused than normal, extend them a little time or tolerance. Adding additional pressure or disappointment to their plate won’t make their condition any easier.

6. Where Do You See This Relationship Going?

This question is the ultimate relationship catalyst or destroyer. If you and the person you’re “just having fun with” are feeling more of the feels lately, it might be time to bust out this favourite. You’ll either learn that you’re both on the same page and looking to take the next step, or that he’s just not that into you. The moment you start to feel the flutter of butterflies in your tummy is the moment that you should take caution. Don’t let yourself jump into the river of love without knowing if it’s something you both want. Once you get that confirmation, feel free to pop on those rose-coloured glasses and start calling each other the cutest of pet names. It’s a conversation that will fill you with happiness or disappointment, but don’t let the fear of getting it started hold you back.

5. Do You Want Children?

Asking the right questions in a soon-to-be-serious relationship will determine which path the union will go down. Right up there with questions about religion, marriage, and overall values, asking about their take on children will provide you with the details to build your case either for or against spending the rest of your life with someone. What if you don’t want children and they do? What if you can’t have children? Is your partner prepared to face that challenge with you and explore other options, or no? This question is heavy, for obvious reasons. Having children is often viewed as a piece of the puzzle that is life, and many people can feel incomplete without fulfilling this piece. The bigger question here is one that people are too afraid to ask, and that is, will your love be enough? Deep, right?

4. Am I Fulfilling Your Needs?

If you’re really looking to jumpstart a conversation to keep you up all night, this question’s the kicker. This one will cover most of the questions we discussed above, from monogamy to fetishes, but can also include some answers you may have never considered. The needs of your partner, employer, or service provider can be difficult to understand. You’re no mind reader! Asking this question is a must if you want to maintain a healthy and happy relationship between you and someone you care about. The answer to this question will let you know if your husband needs you to be more assertive in the bedroom, if your boss wants you to take on more of a leadership role, or if you’re tipping your hairstylist enough. Either way, take it as an opportunity to learn and improve.

3. Do You Have Any STI’s?

Alright, this one is just standard for anyone who is about to get down and dirty with someone they don’t know, or even those they DO know! If you’re about to combine genitalia with another person for the first time, you have to ask this important question. They teach it to us all in school, and yet it’s a question many people are afraid to ask. What if I offend them? What if they say yes? What if the fun time we’re having is ruined? Of course, this question creates a whole other set of them, but this answer has the potential to affect your health in a negative way. Do you really want to roll that dice because you’re too embarrassed to ask? There’s no sexy way to ask, but maybe try something like, “Yeah, mmm, that’s nice. You’re so hot. Got any diseases I should know about?”

2. Are You Into Any Fetishes That I Should Know About?

When it comes to the joys sought in the bedroom, we can all be into some pretty unique things like sensual toys, candle wax, and edibles. When you’re being intimate with someone on the regular, it can be nice to open up and be honest about the ways your fancies get tickled. If your partner is willing to participate, it can strengthen your bond and increase your chemistry. Oooh la la! While most fetishes are innocent, some can be shocking to others. Toe sucking may be your jam, but to a person who thinks feet are gross, it can be the furthest thing from a turn on. Knowing about your partner’s interests may make or break your would-be relationship, but hey, in times like these, isn’t it better to know?

1. Do You Like Butt Stuff?

Crazy as it may be to ask, there are a lot of people who enjoy (and prefer) to take the backdoor to Pleasure Town. It’s become such a common experience among both men and women that making a move down south has become as ordinary as slipping someone the tongue during a make-out sesh. Some partners may be cool with this move, but there are a lot of people who are uncomfortable with it and would prefer that their bum remain an exit only. When it comes to “butt stuff”, remember that it isn’t just penetration you have to ask about; do they like spanking, caressing, cheek kisses, or something else? Getting the answer is important to not only know what you’re getting into, but also to let you know how to make the experience fun for the both of you.

By JESSICA WRIGHT for TheTalko