Two weeks ago I swiped right to every single man on Bumble for 3 minutes straight. I ended up with roughly 90 matches (a few are still rolling in). I gave each match the exact same prompt:



What have you always wanted to ask a woman? Let's do this.


I can't promise that we will meet up. I can't promise that if we do we will be attracted to each other. What I can promise is that you can ask me one question; however ridiculous, personal, or seemingly inappropriate as you want. And if it is asked in a respectful and intelligent way, I will answer honestly. What have you always wanted to ask a stranger? What have you always wanted to ask a woman? Let's do this.

So, why did I do this? I wish I could say “Because I wanted to experiment with giving men a safe place to be vulnerable.” or some bullshit like that. But if I’m being totally honest here, I was a little tipsy and a little stoned and a lot bored, and thought it would be entertaining. I was soooooo right.

The responses were all over the board. Some were bizarre. Some were DEEPLY personal. Most were very thoughtful. And only ONE was disrespectful (and it was only mildly disrespectful at that!). I expected there to be a lot more sex questions and a lot more rude/vulgar responses. Boy was I wrong (and I probably need to find a therapist to help me unpack why I always expect the worst in men…)! 

Aaaaaanyhoosal, let’s get started! 


  1. questions have not been edited.

  2. If you want to read my response, click on the question.

  3. Some of them aren't that entertaining.

  4. Some of them are.

  5. Words. Words. Words. 

  6. ***Fun bonus game!!! I actually ended up going on a date with one out of these 43 questions (wasn’t my intention). First person to guess correctly (in the comments section) gets a photoshopped picture of Dwayne “The Rock” Johnson’s face pasted onto a kitten’s body!***




+ Damn! Why not I’ll go all in on this. Gulp: I fractured my Johnson last year and now it’s bent a bit to the left and I’m horribly self conscious and frankly despairing about it to the point I’ve barely been sexually active - but wonder if a woman would even care. Issues are purely aesthetic but you know how we all are re: our bodies. Do we men blow these things out of proportion?

Thank you for asking that in such an honest and respectful way! I don’t know a single woman (and I know a lot of women) that would ever care about the angle of the dangle. All penises and all vaginas are different and some fit better together than others. Speaking personally, and based on my friends, none of us really care about how the dick looks. (That’s why dick pics are comical at best.) We just don’t care what they look like. It is a functional organ and if it functions and is in a spectrum of size that woman likes, we don’t give a shit. It would be like if someone told me there is a phenomenal car mechanic, and he can fix everything and he gets the job done well the first time. But then they tell me that he sometimes mixes his plaids with stripes. Seriously??? Who gives a shit! I just want a mechanic that can get the job done! Go out there and have some awesome safe sex and be confident that the woman you’re with seriously doesn’t care that your penis is slightly bent.

+ If you could decide a punishment for the slew of recent celebrity sex offenders that would set an example and convey the message that behavior like theirs is not tolerable (outside of jail time and fines), what would that punishment be?

Oooooh, GOOD ONE! I would put each man in a room with every person that he violated (if the victim was okay with that). I would have them go down the line of victims and ask each individual “What did I do to you, and how has it affected your life?” They would have to listen to every single detail of every story. Family members/spouses/friends would be allowed to chime in and say how the change in their loved one affected them as well. The man would have to apologize. All of this would be filmed and released on the internet.


how do ladies work?



+ When women start to tell a story about a problem, how am I to know if you're looking for solutions or moral support? Is there some kind of secret signal? My brain is 100% trained to look for solutions to problems.

Such a great question! Generally speaking, men and women have different communication styles. Most of the time when we talk to each other we are looking for moral support and then that sometimes turns into a solution. I have a best friend who is incredibly solutions based and early on I told her I didn’t need to find a fix, I just needed her to tell me how bad my situation sucked. So now she simply asks “Okay, do you just need me to listen and support you, or are you looking for a solution?” I HIGHLY recommend that approach for you. If the woman wants support, it’s your role to listen and say things like “Whoa. I could imagine that’s really frustrating!” Listen, validate and empathize if you can. Just ask. Women will dig it.

+ From the men you have dated. What has been missing? That you look for in a man.

Every man is different. As a whole? Childlike enthusiasm. "This is so fun!" "That is so cool!" "Oooh how does that work?!?" "Oh wow, you're really pretty!" You'd be amazed at how magical that quality is in a man and how women are overwhelmingly drawn to it.

+ Well that is interesting. Hmm... why is that every girl needs to be paid for, entertained, and taken care of. I mean, for once, could a girl possible take me out? Ask me what I want to do? I swear every female I've met just wants money and alcohol, and say they don't.

I can’t speak on behalf of all women, just myself and my friends, we don’t. I come from the school of thought that whomever asks the other out on the date is the one who pays. I went on a first date last week and the guy bought the drinks at the first bar and I bought the drinks at the second bar. I took a guy out last month and paid for the whole evening because I’m the one who asked. This isn’t uncommon, but if you are the one asking the woman out there’s a chance she believes in this same school of thought. It’s nice to be treated well, all humans want that. You are dating the wrong women.

+ What about when picking where to eat? Do women just want men to pick? What happens when any number of girls are going out to eat...who chooses and how? I don’t just see random groups of women wandering the street starving so picking a restaurant is possible somehow, I’m sure of it.

I’m currently having this same conversation (ask me any question) with 70 other men right now, and I haven’t been answering second questions. But you are being funny so I’ll totally answer your second question. I’m assuming this is for a first dinner date? If so, ask her what part(s) of town she prefers. Then narrow that down to 3 choices. ex) “We can go to ___ for something light and easy (nachos/tapas/casual). We can go to ___ for something a little more unique (ethiopian, new weird place, hole in the wall). Or we can go to ___ because they have awesome ___. (something contemporary and moderately priced). Let me know what you’re feeling.” She’s stoked because you made some decisions, and doesn’t feel disappointed because you gave her options.

+ What's the number one reason you'll stop talking to a man?

On this app or in real life?

Before you've met them?

They're boring. They've asked something I've been asked a million times. They aren't creative. They don't play. They don't show any genuine interest. "How are you?" "How's your day going?" "What's up?" Or "how about you?" As a follow up question. We get hundreds of matches. If you don't stand out, I'll stop talking to you.

+ Why do women seem to go after men who are assholes?

We don’t go after assholes as the primary goal. Assholery are just the terrible qualities that we tolerate because other aspects of the man are great. Think of one specific asshole that a chick you liked went after. Was he super confident? Exciting? Really funny? Successful? Attractive? We compromise with the fact that the dude might be a jerk because the other parts are great. If you are a super nice and boring dude, you aren’t a nice guy who is losing out to assholes. You are a boring guy who is losing out to interesting guys. I’m not saying this is good, but it is the truth.

+ What's the worst and best approach you have ever received online or in real life?

Worst: there are tons and mostly it’s online because men don’t approach women in real life anymore. A lot of wildly vulgar things that I’m assuming they are doing because they think it’s funny, but really it adds up and makes women expect the worst out of men. Ex.) “Let me cum in ur face”. Real opening line. Best approach: men that still approach women in real life will always be light years ahead of online men. If it’s done in a respectful and non aggressive way it is always flattering and has a much higher success rate. I had a man come up to me when I was with two friends at a bar and say “I know you are with your friends right now and I don’t know if you are single, but if you are my name is Chris and I think you are strikingly beautiful. And if you aren’t, I still think you are strikingly beautiful and I would have regretted not telling you, either way.”

+ What do you think is the number one blunder men make when flirting with or hitting on women? (Being cocky is too easy of an answer. Hoping for something thoughtful)

I’ll pick two flirting mistakes that are most common: one is a general lack of respect. Being crude. Not respecting that the woman might not want to talk to you. Inappropriate jokes or comments. The second is making the conversation too much about themselves. Men often think that by talking about all of their accomplishments or stories or trying to be funny that the woman will be impressed and therefore interested. Ask her questions. Talk about general things and not just yourself or her (that’s my preferred form of flirtation). Play a bar game, play 21 questions… Just don’t talk about yourself nonstop for 15 minutes.


whooooaaaa, broooo...

+ How does it feel to be the most sacred creation the universe has ever manifested? You see, women have been given a job that only a woman could handle. You have been chosen to be the tunnel from which all infant spirits begin their transformation into this material dimension. The importance of such a heavy burden to bear is lost on today’s society. It’s a major reason why men disenfranchise women. Collectively we are terrified that y’all are the chosen ones. So, how does it feel?

WHOA. That’s a hard one for me to answer honestly, because I don’t feel that way. I don’t have a strong maternal instinct and I have never seen myself having children. I agree that women aren’t respected as much as they should be, but I don’t think that respect should be based solely on the fact that they are capable of having children. I am neither less than, nor superior to a man simply because of my gender. Being a woman is impossibly frustrating at times, I won’t deny that. I would like to be seen and treated as an equal, but I love being a woman. So, how does it feel to be one of those baby making creatures that you described? I have no idea. How does it feel to be me? I feel strong, intelligent, capable, bold, scared, frustrated, angry, grateful, hopeful…


Keepin' it light:

+ Would you rather be stranded on a desert island with one person that you picked, or 5 random people? 🤔

I like that question! I’m a social person, and honestly I think I would get sick of anyone if they were my only person. So I’ll go with 5 randoms.

+ Would you rather go backwards or forwards in time and when and where would you go?

Forward by 200 years. To see if we figured out anyway to not totally kill our planet and each other. Then hopefully I could find some brilliant engineers and policy makers to implement those solutions immediately.

+ Ha. It sounds like you want to field some whacky questions but I can’t think of anything that has been weighing on my mind, but this game sounds fun. What would you ask?

What do you love the most about yourself?

+ Favorite podcasts?

Radiolab, 2 dope queens, the moth, ted radio hour

+ This is a big decision. One question. I better make it a good one... Before that though, let me just say, thank you for not just saying hi. There's pretty much zero effort in that. Also, you have a really great smile. So here's my ONE question, can I have your phone number? Just kidding 😉 Actually, here's my question. .... It's snowing out. It's the weekend. What does your perfect day look like?

You’re welcome and I agree! Also, thank you for the nice compliment!

Perfect day: wake up around 7:30, have fantastic, light hearted, morning sex with a funny tall hunk sleeping next to me. Roll out of bed and go pour a big ass mug of coffee and start packing to go snowshoeing with 10 of my best friends and their dogs. We stop for breakfast burritos on our way to the mountains. Everyone is in a ridiculous mood and we make a lot of inappropriate snowmen and get in snowball fights. We roll back home around 2. Me, my two roommates (who are also two of my best friends) and the tall funny hunk get home, shower and someone goes and picks up Pho for dinner. Then we all eat an edible and get super silly and watch a terrible cheesy movie to make fun of and play catch phrase until we laugh so hard everyone is crying. Everyone goes to bed, tall hunk gives me a full body massage, we have phenomenal sweaty intense nighttime sex, and go to sleep.

+ If you were offered a one way ticket to colonize mars, would you take it?

Noooope. No. Way. Earth is the best. Water. Trees. Air. Breathing that air. Plus I have an overwhelmingly uneasy feeling about space. (I hope you have a beautiful start to your week as well!)

+ I have two questions if you will allow. First, what are the three most important characteristics to you when looking for the right person. Secondly, and probably vastly more important....The Office or Parks and Rec!? And....Go!

I haven’t been answering two questions, but your second one is so easy…

  1. Genuine kindness
  2. Playfulness
  3. Height

Parks and Rec. Hands down.

+ Tinder Opener #5: Your Sunday breakfast personality is __? A) Waffles & pancakes, slowly savored. B) Apple & granola bar on the run. C) Aggressive mimosas. D) Sleeping til lunch.?

Combo: A) sub eggs and hash browns (I’m not that sweet) and C) sub light-hearted for aggressive. (Aggressive mimosa is an oxymoron).

+ What is your guilty shopping pleasure?

Vintage dresses at thrift stores and awesome cheese.

+ Are you into psychedelics?

Why is a mushroom the first vegetable to be invited to a party? Because he's a fun-guy.


gettin' deep:

+ What is your greatest fear when it comes to love and your relationships? And how do you overcome it? Or have you yet?

My greatest fear is that the love that is left over for me is mediocre. That I've lived too much to be wildly in love, and that the most I can hope for is someone that is nice enough to me that I won't leave and interesting enough that I won't fall asleep. I have not overcome it at all. Phenomenal question.

Great answer. I definitely can see what you mean, and I believe you'll find that love still. I'm willing to answer completely honestly as well, if you'd like to ask me one.

What about you makes women happy?

That I still believe in being a gentleman and treat her like she's the most important woman in the room. Because she is. I like to open doors, take her coat, and treat her like she's something special. Keep in mind I also know she's independent and can handle her own. But she appreciates the care and the tenderness.

+ This is very intriguing to say the least, and I’ve put thought into it so here it goes. Have you ever betrayed someone you loved? Justify your position either way, please.

Yes. I think we all have. I legit looked up the definition of betray so that I could answer this honestly. Betray: to lead astray, to deliver to an enemy, to fail or desert especially in time of need, to reveal unintentionally. I think loving people isn’t easy and it isn’t black and white. I don’t hurt people intentionally but sometimes being true to myself means that I don’t behave how others want me to, and that can be hurtful. I try to do it in the most respectful way possible. Everyone has to act within their own truth but that doesn’t mean it’s acceptable to do so with the intention of harm.

+ What's your greatest fear at this very moment in your life?

That I’m not even remotely close to reaching my potential, and I don’t even know where to start to figure out what that means. (what a phenomenally lucky and privileged person to have such an existential fear)

+ What brings you the greatest pleasure?

I’ll go with the definition of pleasure as “a feeling of happiness, enjoyment or satisfaction” Accomplishing something really difficult, that took a long time, where I wasn’t sure if I was capable of accomplishing it. If you were curious about physical pleasure, you should have been more specific.

+ What lights you up inside and inspires and motivates you to be the best you that you can be?

Wowie, coming out swinging I see! Seeing humans be painfully beautiful to each other and the world, especially in unexpected or challenging times. Knowing that I could have that effect on others as well. Knowing that one small action could change someone’s entire day/week/life. Making a concerted effort to do those small actions when possible. That lights me up like a Christmas tree. Great question!

+ Wow, that is a tough opener 😊 Good one though. I've never been shy about asking women questions, so I'm pretty sure I have most general ones covered. And while I'm curious what your thoughts are on me, I don't think you have enough information and I'm not about to waste my one question on that. So that leaves learning something about you. And no promise of a followup question and very little starting information. So I'll go with this. What have you always wanted to do, but haven't yet? If there is more than one answer, pick the one that the fewest people know about.

VERY thoughtful response and question! Well done! Simple answer: dive with whale sharks. Deeper answer: make a significant positive difference in a large number of people’s lives.

+ Well honestly the questions I have always wanted to ask a lady that is guaranteed to be honest is after we had sex. I don’t really have one for someone the first time we meet. So, to just ask you any question, what is the most “craziest” thing you have ever done?

Yeah, I can’t help you with the sex bit. “Most craziest” (you can just say craziest) thing I’ve ever done? Ummm I bought a one way ticket to Thailand and ended up staying for 8 months. If you were asking what is the craziest sexual thing I’ve ever done, you should have been more specific.

+ You obviously like nature. Does it lead you to believe it God or does it lead you the other way?

I don’t believe in God in the traditional sense of the word. I believe that there is something else going on that our tiny human peanut brains can’t comprehend. I believe that in the same way forest systems are connected through roots and fungus, we are connected through some sort of energy. I believe being out in the woods makes me feel closer to that than when I’m sitting behind my computer. I think our view of god is very limited, but the atoms that make up me, and you, and my dog, and a fern tree are all the same - and maybe they can affect each other - and maybe that’s god.


expected fluffy nonsense

+ What’s up with “bees knees”?

Like where does that saying come from?!? I can't google it because that's cheating, my best guess is: someone was on drugs and thought about how important bees are. Then they thought of something important on bees that rhymes and is highly underrated/under appreciated. And that's where the saying comes from. "This thing is great and important and wildly under appreciated."

+ Does your doggie like that pack??

Normally, no. That day, she loved it. Her paws were cold from snowshoeing.

+ Wow. That's a powerful opening message and very unique. After much consideration and consultation with friends and family, here is my question: How much wood could a woodchuck chuck if a woodchuck would chuck wood? 😜😉😜

A: 27

+ Who is the most underrated character from Bob’s Burgers?

I've never seen Bob's Burgers.


Am i special?

+ Why did you reach out to me? What made you want to message me?

I swiped right to every man for three minutes and asked everyone the same question. I said I would be honest.

+ That’s definitely a different approach. I️ dig it. Oh the possibilities to ask haha. I’ll keep it pretty simple. What about me wanted you to swipe right?

I swiped right to every man for three minutes and asked everyone the same question. I said I would be honest.

+ Hello Katie, this is an impressive and elaborate promise/non-promise intro! Is this a cut and paste that you send out to all of your Bumble suitors or do you put this much intellect into each one?

Control C. Control V.






A few called me on my shit:

+ That’s a rather curious intro. What do you seek on Bumble? That’s my question. I’m not looking for a pen pal or shallow engagements.

As a whole, I’m looking on Bumble for the same thing that I’m looking for in real life. One really great date. One that I laugh more than anything else. I have butterflies and my face hurts from smiling and the conversation is fantastic and we kiss mid date and at the end of the date because that’s just the way it’s going. Then that date leads to many many many other great dates that turn into all sorts of adventures. But right now, I asked this same question to 70 men and I guess I’m looking for some sort of deeper entertainment, because the shallowness of this app is crushing my soul.

+ What is your true intention by offering this to people?

There are a couple. 1. All of the frivolous and uncreative conversation starters get really really really boring after awhile. And have ultimately led to a string of unsuccessful (to varying degrees) dates. Maybe by starting off with total honesty and vulnerability, it will lead to something more genuine and promising. 2. I write a blog. I asked 70 men this exact question and I’m very curious as to what men are curious about.

+ Lol it's an interesting proposition, but it comes across weird, Plus everybody likes to talk about themselves so it really just comes across as a bad pick up line like' hey ask me something about me' pretty sure there's not a question that I don't know the answer to or I'm dying to find out, of course the obvious easy perv question would go straight to the sexual but that's not original. So I guess I'd just ask that from a woman's perspective, what is one thing that you think men need to know about women that we don't?

Oh man! I mean there are a lot of general ones that most men have heard but don’t really practice. One that I’ve mentioned several times to men and they always seem shocked, is that women don’t really get hit on in real life anymore. At least not women that I know in this region (and I know a lot of women). I would say, on average, I get approached once every three months. Most of my friends are in that range as well. Why is this important? If you approach a woman in real life, in a kind and respectful way, you will be 4.3 billion light years ahead of all the men on these dating apps. Maybe you already do that, in which case, all of us ladies would like to applaud you. That and goofy, childlike enthusiasm, for pretty much anything, is one of the most attractive things a man could ever demonstrate.

Haha thanks for the honest and thoughtful reply. So what’s your aim here - are you just enjoying these sorts of philosophical conversations, or am I going to see this in an urban outfitters coffee table book someday?

(Anyone have an #urbanoutfitters hookup? Just kidding, fuck that bigoted swap meet.)







There's always gotta be one...

+ Well already breaking my heart with broken promises! 1st-If we were to get attacked right now by ( terrorist, gunman, bear, mountain lion, aliens, ex girlfriend) are you going to help me fight or run away like a lil bitch? I need to know. 2nd- Is there a timeline when a guy can fart around a girl he’s dating (First date, third, first sex session, never? 🤷🏽‍♂️

  1. Don’t say “lil’ bitch” or infer that ex girlfriends are the same as a terrorist or gunman. Not answering that question for those reasons.

  2. If you had been more respectful I would have said, “everyone passes gas. I would say a good rule of thumb is to excuse yourself to the restroom for the first few months of dating. Unless she starts farting then follow her lead. If it slips it slips, don’t be gross about it and don’t make a stupid teenage joke.” but since you said “first date or first sex session” you are clearly just being rude and trying to shock me. In which case, if you behave in person like the way you are behaving now, I would assume you fart anytime and anywhere you want and never make it to a second date. So do what you want.


And then this guy gives me the perfect summary question! 

And then this guy gives me the perfect summary question! 

+ Wow, this is probably one of the most in-depth, intellectual opening statements/questions I have ever read. What are some of your best responses you’ve received to this question and why?

  1. When women start to tell a story about a problem, how am I to know if you're looking for solutions or moral support? Is there some kind of secret signal? My brain is 100% trained to look for solutions to problems.
  2. Damn! Why not I’ll go all in on this. Gulp: I fractured my Johnson last year and now it’s bent a bit to the left and I’m horribly self conscious and frankly despairing about it to the point I’ve barely been sexually active - but wonder if a woman would even care. Issues are purely aesthetic but you know how we all are re: our bodies. Do we men blow these things out of proportion?
  3. What do you think is the number one blunder men make when flirting with or hitting on women?
  4. If you could decide a punishment for the slew of recent celebrity sex offenders that would set an example and convey the message that behavior like theirs is not tolerable (outside of jail time and fines), what would that punishment be?

I liked the first three because they were honest, vulnerable and I think my answers might have actually helped them. I like the last one because it was wildly original, relevant, and it challenged me.

CONCLUSION: I was pleasantly surprised with the level of thoughtfulness and respect, thanks Denver men! This was the most fun I've had on one of these apps, well, ever.

*tips hat

( If you want to ask a question, feel free to contact me! I'm actually going on a SECOND date with one of these 43 questions tonight. Who do you think it was?)


Katie BessertComment