20 Questions That Men And Women Are Afraid To Ask Each Other (With Answers!)

In the name of research, and also in the name of awesome Gchat conversations, I decided recently to sit down with my good buddy and most blessed coworker Christopher Hudspeth for a Q&A session featuring all of the gender-oriented mysteries that plague our respective teams. We went back-and-forth with 10 questions each whose answers have always remained a point of alternating fear and curiosity, and here are the divine results:

Christopher: For years now I’ve heard whispers of women gauging male attractiveness by the shoes they’re wearing. Is this actually true and will my unkempt, beat up Converse sneakers leave me destined for heartbreak?

Chelsea: Obviously that is a hugely personal/individual choice, but I’d say that a lot of women do judge based on shoes to some degree, largely because we are expected to always look a certain way and present ourselves with a certain amount of care, and it often feels lazy/hypocritical when dudes completely abandon the practice themselves.

Chelsea: Sometimes it seems like men in relationships are, to some degree, looking for a replacement for their mom. Is every relationship doomed to having the woman clean up after/nag her guy to a certain degree? And on some level, is this appreciated?

Christopher: Much like with our mothers, I think a lot of guys who’ve had the luxury of being picked up after will try testing the dust bunnies and seeing what the limits to their messiness are. A shirt on the floor will turn into a pile of dirty laundry and an unwashed plate will lead to a sink full of dirty dishes if the standards aren’t set. It’s not nagging so much as a smack back to reality.

And whether it’s appreciated or not it’s necessary, mainly because the difference between your mom & your partner’s cleanliness criteria is 10+ years — meaning we’re all fully grown, capable adults now.

Christopher: Dudes taking selfies seems to have become somewhat of a taboo. Is it truly frowned upon when you see a guy having a solo photoshoot and posting the pictures on his social media?

Chelsea: I don’t personally care, I think it’s cute and sweet and something that a lot of people like to do because who doesn’t want to look nice? But at the same time I think that a lot of women likely perceive it as a vain or superficial act, and as those are qualities typically (and unfairly) associated with the feminine, women who are invested in/attracted to standard gender roles probably dislike it.

That said, I don’t think anyone who cares that much about a guy taking a selfie is worth your time to pursue. It’s a harmless activity, and everyone should be able to have fun and take pictures when they feel like it. Selfies for everyone!

Chelsea: I often doubt the sincerity of Professional Male Feminists, or dudes who constantly proclaim/preach about how feminist they are and talk about women’s issues with any kind of authority. It often strikes me as really insincere/self-serving/brownie point-collecting. Does it give guys the icks as much as it gives some women?

Christopher: I personally think it’s difficult for male feminists from the jump because while they may mean well, the whole being a man part is unavoidable, often leading to overcompensation that makes everything they say and do come off as disingenuous. Of course any logically thinking individual wants equality, and supporting is one thing, but we’re only able to speak on the highest level about things we comprehend and ultimately, only women know firsthand what it’s like to deal with these particular issues.

Christopher: Is a catcall EVER the least bit flattering? Does the attractiveness of the caller play into how obnoxious or gratifying it is?

Chelsea: No it’s not, because no dude you would ever be interested in would do that. Even if he were cute (and they never are), you would immediately lose all respect for him immediately if he just started yelling shit at you while you were trying to walk to work. Compliments from a cute guy are one thing, catcalling is something completely different and totally unwanted.

Chelsea: Why are so many men immediately turned off/feel the need to make an asshole comment if you in any way out yourself as a feminist?

Christopher: If the claws come out the instant he hears ‘feminist’, it might be a red flag that he’s got some control issues. Or, it might be a result of the bad reputation being developed as a result of elitists masquerading around under the title of feminist. Often times these days, male opinions and thoughts aren’t even something “feminists” want to hear, because they’re all chauvinistic, scummy jerks in their eyes. When it becomes less about equality and more about bashing a gender, nobody wins and men (unfairly) bundle feminists and elitists together.

Christopher: Normally it isn’t common for a girl to approve of her boyfriend having mostly female friends. Is the whole “I have a ton of guy friends because girls are catty” thing legit, or is this some ladies’ excuse to be around people they’re attracted to?

Chelsea: I think that it’s neither. I think girls who go on about how bitchy other girls are and why they therefore can’t be friends with them are pretty insecure and have their own problems with women — I don’t think it’s just about being around guys they are hot for. I think that any person, male or female, who “can’t” be friends with their own gender has some serious issues about other people. If a woman doesn’t like the fact that you are exclusively friends with women, I would say it’s more about suspicion as to why you can’t hang out with dudes too, rather than fear that you’re going to cheat. That could be part of it, but it’s not a problem that exists in a vacuum.

Chelsea: Why do some dudes refuse to go down on women? Like that just seems like such a lame thing to not do, when half of sex is about enjoying the other person enjoying him or herself, and yet so many guys are weird about it. Explain!

Christopher: WHO ARE THESE GUYS? On behalf of real men and those who enjoy giving as much, if not more than receiving, I’m sorry to any woman who has experienced such nonsense. I will say that I’ve noticed it seems to be more common for women to decline going down South as well, but that’s not the matter at mouth. Personally, if I were a woman and my guy wasn’t interested in my satisfaction, I’d give him one opportunity to read A Gentlemen’s Guide To Cunnilingus before reevaluating the relationship, as a healthy, happy sex life is crucial.

Christopher: A lot of the time, before sex, women make a quick trip to the bathroom. Generally speaking, is something crazy going on in there or is it actually just a quick pee/something anticlimactic?

Chelsea: It’s usually to either pee or just generally freshen up. No great mystery there, unfortunately.

Chelsea: Why does it seem like so many guys in their 20s are actively avoiding relationships, or can’t stand to be in them for too long?

Christopher: I don’t want to put the burden of this trend strictly on guys, but there’s most certainly a development in the dating world that has rendered labels and actual commitment less common. Boyfriend/Girlfriend have been tossed aside, and instead, you’ll hear people say that they’re “talking to” someone, which is basically going on dates, texting, calling and spending time like a couple would, without feeling 100% obligated to be loyal if any fresher, more attractive options suddenly pop up. As a result, you see people fighting off off full blown relationships for as long as they can get away with sampling other trays.

Christopher: A lot of the time, dudes are known for loving seeing revealing photos of women — is there an equivalent to a woman’s bikini or lingerie pic? Is a shirtless picture of a guy you find attractive something you’ll call friends over to ogle at and discuss?

Chelsea: I think a lot of women find photos of well-dressed, well-styled men to be pretty sexy. Showing skin is not as important as looking put-together in whatever style you’re going for. It could be a nice suit and side part with glasses, or a well-maintained beard and plaid work shirt with suspenders, or a nice sweater and jacket for a winter day. Just a guy who looks like he knows how to take care of himself. Look at Tumblr — every selfie/outfit photo of a really nicely put-together dude (of all different body types and styles) tends to accrue a zillion notes pretty quickly.

Chelsea: Why do men send the most gross, inappropriate, horrible opening lines on dating websites? WHY IS THAT A THING THAT YOU DO?

Christopher: I regret to inform you that some men were born without that portion of the brain that sends common sense, self awareness and respect signals when it comes to courting women they’d potentially like to date, or hookup with. I think horniness clouds a lot of dudes judgment and their terrible idea seems like it might actually work, when they should really fap that stupidity out and clear their mind. I’ve seen some of the vulgar, ridiculous openings on numerous occasions and perhaps a call-out website where you post screencaps identifying these offenders is a solution? Because i’ve had female friends show me some RUDE openers and I’m shocked.

Christopher: Not always, but probably more often than expected, men have sexual thoughts or even pleasure themselves to various women they know in real life — do women choose a guy to masturbate to or is their process different/more complex?

Chelsea: This is one thing that I feel unqualified to answer to on behalf of all women, or even a lot of women, but I do think that when women think about a guy in that way it’s often because they have real feelings for him in some way, it’s not just because they find him physically hot. I mean, they might, but I feel like there is often more involvement than that, like they have a crush on him or miss him after a breakup or something. It’s not just like, “Ooh, I thought of Ryan Gosling suddenly, rub rub rub.” Or maybe it is, but not for a lot of people.

Chelsea: What is something that you have found that women think that men enjoy sexually, that they don’t actually enjoy that much in practice?

Christopher: Butt stuff. This is easily the most commonly mentioned bedroom activity that I hear guys say they were surprised by, and not necessarily in a good way. I think a lot of dudes know how terrible of a place their butt is, therefor, they don’t want any of your ventures to take place there. Still, I’m sure there are a fair share who enjoy it, so it’s all a matter of individual preference ultimately.

Christopher: When a guy is turned on in public it can be quite a struggle, as there’s blatant visual evidence of his sentiments. Do women get strongly aroused in public settings and if they do, are they literally able to walk around like normal, without showing a hint of what’s going on inside?

Chelsea: You would have to be a geyser of arousal to not be able to hide it, so I would say you’re generally okay, even if you do get really worked up over something. That said, we have to deal with periods cropping up at untimely moments, so we know what it’s like to be humiliated by your crotch in public all too well.

Chelsea: How often do guys complain about their girlfriends to their friends in a relationship — and don’t lie, we know you do it. We just sometimes worry that you’re overestimating how “crazy” we are and making us look like assholes to your friends.

Christopher: I was in the process of writing out an honest answer and some dudes in black suits & shades approached me, so I’m going to go ahead and say that often times, if you’re normal you’re called crazy and if you’re actually crazy you’re called nothing at all out of fear it’ll get back to you.

Christopher: What is it about the word “relax” and the phrase “calm down” that make most women do anything but?

Chelsea: Because it completely nullifies any legitimate emotion we might be experiencing. It’s often used against us even when we’re reacting in a way that is perfectly proportionate to the situation, and it feels incredibly condescending and infantilizing. It is something that just gets under our skin because it reminds us of every time we have been told, as little girls, to just shut up and be pretty.

Chelsea: What is the most hurtful thing a woman can tell a man, in an argument or otherwise?

Christopher: What exactly are you trying to do with these weapons of mass destruction? The words that hurt depend very much on the particular guy, but I can say that often times it’s not just about what hurtful things you say, but what hurtful things you make a man believe you genuinely mean. Something as simple as, “I never felt safe with you.” could do serious damage to the male psyche if he actually believes it.

Christopher: Being able to pee anywhere anytime is one of the true perks of being a man. What are a few of the lesser-known glories of being a woman?

Chelsea: Men doing really nice things for you, such as holding doors or letting you sit down on public transport, or carrying things that are too heavy for you. It can be really sweet to be treated like a princess from time to time. And if you’re a dude, it’s like, “Hah, fuck you, enjoy carrying that enormous grocery bag up those six flights of stairs.” It’s pretty cool. Thought Catalog Logo Mark


About the author

Chelsea Fagan

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

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