16 Embarrassingly Honest Questions Men And Women Are Afraid To Ask Each Other (With Answers!)

A while back, TC Heartthrob Chris Hudspeth and I asked each other some honest questions about the opposite sex, and got some real answers. But we are still very curious and nosy, so we thought, why not revisit our conversation? Here, 16 more #real questions that we’ve always been a little shy to ask each other.

Chris: I’ve asked this before but I always get vague, foggy, brushed off answers and I’d like a definitive one. Why do women go to the bathroom as a united faction like some sort of potty party regime type deal? And does anything noteworthy tend to happen in those ladies room meetings?

Chelsea: We go to the bathroom together for three reasons, usually:

1. To talk shit about the people we are currently with and/or discuss whether or not we’re going to let the guy who is flirting with us hit it.
2. To share makeup/tampons/oil absorbing sheets/general products that we don’t stock enough of in our purses.
3. Because going to the bathroom alone is boring and a lot of the time there is a line, so it’s nice to have someone to wait around with and talk to.

Also it’s important to note that girls often pee in the same stall. Yes, this means we see each other naked from the waist-down from time to time. No, we don’t care.

Chelsea: How much do guys worry about their penis size, honestly? And do they think it actually feels different for girls, or is it just a pride thing?

Chris: If you had a million bucks in the bank, you wouldn’t be worried about your Netflix auto-charging $8 this month, right? What I’m trying to say is a guy is only concerned about his size if he thinks he’s got something (or lacks something) to be worried about. It probably has a lot to do with the popularity of porn and people wanting to matchup size-wise with adult film actors who were hired based on fitting specific criteria, one of which was a large penis.

Chris: How does putting on eyeliner work? I feel like the process resembles something from a Saw movie and I can’t understand how a pencil around such a sensitive area isn’t excruciating.

Chelsea: This is how I do it, personally (and I use liquid eyeliner): I pull on the side of my eye to get my eyelid all flat and slitty so that I can paint a straight line, then I paint it really slowly (it usually gets a little bit wiggly towards the middle, but whatever, then you do a little flick up at the end to make that little cat-eye thing. Then I attempt to recreate it on the other eye, but it never really looks the same/as good, so I just spend most of the evening trying not to look people head-on so they see my uneven liner.

Chelsea: What do normal guys think of the MRA/Red Pill/Men’s Rights crowd on the internet? And stuff like The Game? Does it seem insane, or like it has some good tips?

Chris: I read The Game and I’ve got to say that I enjoyed it the same way I enjoy WWE ‘rasslin. Yes, I’ll cheer for someone to hit an elbow drop off the top rope but ultimately I understand that it’s fictitious. I do think there are aspects of pickup artist activity that can be useful, but for the most part it seems like elaborate schemes that are ultimately about having confidence in yourself. I’m not too familiar with the Red Pill thing but it’s the internet so I’m sure there’s some not-so-great stuff discussed there. I’d consider myself a somewhat normal guy with a diverse group of friends and when we hang out men’s rights aren’t a huge topic of discussion. I feel like my rights and manhood aren’t currently in any danger.

Chris: Why does it seem so often that women hate on other women at any given opportunity? Even when it’s not extreme, I had a friend who was just “one of the guys” but when girls would come by she’s be friendly, then the second they left she’d, at the very least, make some type of negative remark.

Chelsea: In general, I feel like women are so encouraged to be in competition with each other for the attention of men — by the media, even sometimes by the people who raise us — that it’s hard not to go to that default mode of “Get this bitch out of my territory. And her outfit is not even that cute.” But in my experience, the “just one of the guys” girls tend to be the worst. I used to be like that, and I really prized myself on not liking/not being like other girls. Ultimately, it was because I was insecure, and needed to cut other people down to make myself feel better. It wasn’t much more complex than that.

Chelsea: So many women’s magazines talk about the “finger in the butt during the blowjob” as the ultimate, boss-level sex move. Is this a legitimate thing we should try, or no?

Chris: No. Nope. Nah. People say this is a don’t-knock-it-‘til-you-try-it type thing so I won’t knock it but I also won’t try it. I don’t speak for all buttholes, but I think some magazines may be getting ahead of themselves by casually recommending something so traumatizing.

Chris: What is the most commonly missed activity or action in the bedroom that all guys should be doing?

Chelsea: Obviously this varies from couple to couple, but in my experience, one of the most overlooked activities is the most simple one — kissing. I know that it’s not always the most physically satisfying thing you can do, but kissing, when done right, can be the best foreplay. You can do those light little kisses where you barely touch lips, or the really deep, involving ones where you feel like you are going to swallow each other whole. (And, best part of all, you can kiss pretty much anywhere — even while on the walk home from a good date!) My personal favorite is the kiss where you’re talk/whispering really softly in-between kisses and you can feel the words on each others’ lips. Why don’t more guys spend time on kissing??

Chelsea: What is the most common thing women do that makes guys lose interest?

Chris: Brace yourself for impact because this is going to be jarring:

The most common thing women do that makes guys lose interest is… be interested in him. At least this seems to be the case from my observations and conversations over the years. There seem to be two common reasons why this happens:

1. It was a challenge to get interest and once that’s been acquired the game is over.

2. They don’t feel great about their own personal value and if you can be into someone as mediocre as them, that’s a turnoff. None of this makes sense, but it happens.

Chris: What do you do with an entire roll of toilet paper so quickly? Like, how?

Chelsea: Lmao. I don’t know, honestly. Well, I mean, I do. You guys only wipe half of the time, we wipe every time. We also use it for makeup removal/dabbing our underarms/lining the toilet seat if it’s gross/or as an extra line of defense during ~*~mEnSeS~*~. Toilet paper is an all-purpose helper, and if you don’t have the two-ply good stuff when we come over for the first time, it WILL NOT be overlooked.

Chelsea: What is one thing that is going out of style — either in women or in modern relationships — that men are sad to see go?

Chris: Allowing a man you’re uninterested in the opportunity to crash and burn privately is swiftly going out of style. Now there have to be screenshots of his texts and Facebook posts and call outs about failed attempts at courting. The question “What’s the worst that could happen?” is no longer something to find comfort in, because even a feeble imagination can concoct some pretty horrifying worst-case scenarios. Also gauchos. What happened to all of the gauchos?

Chris: Using as many adjectives and analogies as possible, what do multiple, consecutive orgasms feel like?

Chelsea: Well, first we have to establish the difference between “multiple” and “consecutive.” There are some women who experience rapid-fire orgasms, even dozens at a time, which sort of hit her in waves when she climaxes. I have never experienced that, personally, so I can’t really speak to that experience. (And from what I understand, it’s a much less common phenomenon than porn would have you believe, which is sort of true of everything in porn.) But in terms of being able to have, say, five orgasms in one sexual encounter, it’s pretty great, and honestly one of the few concrete examples of #FemalePrivilege that we have. It’s the same thing as a guy would feel, I think — shivers through the body, contractions, a sense of euphoria — except that there’s very little time between how many times it can happen. And just like with men, it can eventually become painful, if you’re overstimulating something that has already been worked on too much. At the end of one of these sessions, it’s simply exhausting. Your whole body is like, “No, enough, no more. Please let me sleep.”

Chelsea: When guys add a girl they’re interested in on Facebook, do they go around her pictures specifically looking for bikini/underwear/tight-fitting dress shots?

Chris: Sometimes guys probably definitely might 100% for sure consider perhaps doing that. The ‘Mobile Uploads’ album is notorious for containing the jackpot photos described in your question.

Chris: When women see a guy they find physically attractive, is imagining having sex with him one of the first few thoughts?

Chelsea: Yes.

Chelsea: Is sex with a condom really that bad? What does it feel like? DESCRIBE IT IN ILLUSTRATIVE DETAIL FOR THOSE OF US WHO HAVE NEVER WORN CONDOMS. We want reasons.

Chris: Oh, absolutely, it’s that unpleasant. I could honestly write you a 5,000 word response on this, but here’s the best immediate example that comes to mind:

Sex with condoms feels like a reverse Christmas where you get to see all of the awesome gifts in advance, then your parents wrap ‘em back up and only allow you to play with them that way.

(And then even if they say that you can take the wrapping paper off if you’d like to, you run the risk of possibly getting coal for the next 18 years.)

Chris: Why can’t you just order when asked initially? Why say no and then try to mooch off of my personal pan pizza shortly thereafter?

Chelsea: I resent this sexist, obnoxious question. I order every time the waiter comes over, even when I’m not that hungry. No man worth being with is a man who will judge me for ordering the appetizer sampler platter.

Chelsea: What is the biggest misconception that women have about how life is for men?

Chris: Perhaps it’s that we’re stonewalls with no intense emotions or feelings. Even guys who are great at containing their feelings still have ‘em. They exist, they’re just well controlled. I know tough dudes and I know some emotionally fragile ones, but for the most part they’re just as vulnerable as women. Thought Catalog Logo Mark

Like this? Read Hooking Up, a collection of essays, musing, complaints, suggestions about modern dating.


About the author

Chelsea Fagan

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

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