His Take: “How Long Can We Keep Sexting?”

His Take questions are answered by our panel of smart, opinionated, and funny dudes.

I’m curious how long it would take for two people who sorta know each other, but live on opposite sides of the country, who are into sexting each other, to finally start to get bored of it? Months? Years? They will most likely never meet, so you would think someone will get bored sending the same photo of their crotches, and trying to come up with some new ways of turning each other on, right? How long do/should sexting relationships last? — Not Bored Yet

Screen Shot 2014-01-08 at 7.14.33 PMBrian: Is this one of those “I’m just asking for a friend” kind of questions? Either way, it sounds like you have something that works for the present and may continue to work for months or years down the road. But if you want to know when you’re going to get bored of it, what does that matter? The only explanation I can think of is you’re worried about getting burned, but you have to keep in mind that, when this fizzles, burns or flames out spec-fuckin-tacularly, the worst that will happen is a whole bunch of nothing. You won’t miss seeing someone you don’t ever see anyway. You won’t miss long-winded romantic emails from a person who… doesn’t send long-winded romantic emails. The time it will take to move on? I give it two hours.

Also, if you think people get bored of seeing crotch photos of the same crotches, look up the figures for how many people follow a specific porn star on Twitter, hoping for Round 26,779 of the same cleavage close-up.

unnamedGuy Friday: There are guys who will regularly pay for webcam shows and buy DVDs of the same porn actress doing lots of different things, so I’m not sure there’s actually a usual cut-off date for watching the same person do sexual stuff; it just kind of ends when it stops being fun anymore. Like most sexual things, I’m of the belief that it can’t go on indefinitely without someone developing feelings for the other person and wanting more, but then again I haven’t had long-term sexting relationships, so what do I know? If you’re not going to pick the guy out of a lineup fully clothed, then roll with it until either of you doesn’t want to anymore.

AndrewDrew: Why is this written in the third person? And why the hypothetical language? Is it possible someone’s concerned aunt is writing this on behalf of her teenage niece? I say that because someone’s aunt is the only person who would use the word “crotches.” Regardless, I’m totally grossed out. Tell your niece to stop texting pictures of her hoo-hah to random dudes. And while we’re at it, I don’t want you getting any funny ideas. You keep your crotch in your pants, lady. You’re someone’s aunt for chrissakes.

* If you’d like to ask the guys a question, simply email me at wendy@dearwendy.com with “His Take” in the subject line and I’ll pass your question along to them.


  1. Painted_lady says:

    Drew, you win. That cracked me up. Wendy, your husband is hilarious.

    1. Agreed! I didn’t understand this letter at all. Is the LW really writing about a friend. Or writing about herself? I was picturing a prude writing this and is sick of her bff sexting someone. Or, maybe a chick who is harboring secret feelings for her super hot dude friend and is tired of him discussing this equally super hot chick he is sexting. I mean, will he ever get bored with her and realize that he too is lusting after girl pal. Probably not.

    2. honeybeenicki says:

      Bonus points for use of the word “hoo-hah,” which also happens to be my favorite word.

    3. I don’t know how I’ve lived this long without the knowledge of who should appropriately use the word crotch 😉

  2. I’m really glad that His Take is back! But… I wish it hadn’t been a facepalm letter. Drew is right, why is this written in the third person? And Brian is right… why does it matter?

  3. LOL at Drew. And good point Guy Friday about the porn thing–the fact that people have porn actor/ress preferences at all sort of means it’s unlikely for someone to get bored of seeing the same person’s junk. So basically, the only way your sexting buddy will get bored is if you…become a boring sexting partner? In which case, s/he’ll probably only move on for a little bit, then come back in a couple months again to test the waters. This sexting partnership could go on for a LONG time, is what I’m saying. Do you want that, LW? Because it sounds like maybe YOU’RE the one who’s getting bored?

  4. So… is this person bored with her sexting buddy and looking for a justification to ask for something new? Haha.

  5. The hypothetical language makes me wonder whether the LW is the one who is already bored, and is wondering when long-distance dude is going to get tired of seeing her hoo-hah. The answer might be: never, but don’t get all out of proportion here, because he’s also not going to get tired of the perpetual panoply of pudenda readily available on the internet. As always, assuming the LW is a woman, when a woman wants to better understand male sexuality, she should be careful what she wishes for.

    1. Painted_lady says:

      Points for alliteration.

      1. Painted_lady says:

        “Perpetual panoply of pudenda” would actually make a great vocal warmup for my theatre kids. Too bad I’d probably get fired for teaching it.

      2. Well, i toyed with “perennial profusion of pussy,” but that’s just tacky, not to mention a lot of alliteration from an anxious academic asshole aspiring to audience accolades.

  6. I read this letter as if it was written by Jaqen H’ghar from Game of Thrones.

    “A man must send a sext.”

    1. Love the obscure reference. well done.

      1. TaraMonster says:

        It’s only on my mind bc I just rewatched the whole series; my boyfriend had never seen it. I have him fully addicted now. The other day he sat up in bed, looked at me very seriously in the eye and said, “A man must take a shower.” I was cracking up.

  7. Anyone else amused by the picture of Atticus Finch next to talk about porn?

    1. Painted_lady says:

      I have such a crush on Gregory Peck as Atticus Finch. I would be all over that shit.

      1. I do too, but it’s more of a crush on a professor or a friend’s dad kind of way, and I don’t want him talking about porn!

    2. Avatar photo Guy Friday says:

      Hey now. It’s not like my face next to it would have made it any better. In fact, it probably would have made it worse.

  8. Avatar photo Addie Pray says:

    Hey who’s Brian? We need an introduction! Tell us all your secrets.

    Have you guys ever gone potty and at the same time started checking out / admiring your freshly waxed crotch with your hand (and kind of forgot you were peeing) and then accidentally tilted your crotch just so, so the pee, instead of streaming downward, shot up and out of the toilet and onto the floor? No? Oh. (Drew’s rant about the word crotch somehow reminded me of that one time that happened to me. So I blame Drew for that tangent).

    1. Avatar photo Addie Pray says:

      B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N — B R I A N — B R I AN — B R I A N — B R I A N — B R I A N . . .

      You forgot to come tell us who you are and all of your secrets.

      1. What would you like to know… Tatum?

      2. Also, Wendy has my bio but I’m not sure when/if it will go up. Here it is, so you can know .001% of my secrets:

        Brian Fairbanks has been a working journalist since he landed a job at the Hartford Courant at the age of 15, going on to write for Gawker, Nerve and AOL as a relationships and pop culture writer. After a tenure of working on books by Hunter S. Thompson and Jack Kerouac, he created videos that aired on the Daily Show and the Rachel Maddow Show and has just completed his first feature film.

      3. Avatar photo Addie Pray says:

        Yes, Tatum! Also go on, we are listening. Also do you know Jimmy Kimmel by any chance?

      4. I don’t. (Was this because I did too much name-dropping in my bio?)

      5. Those bios are quite awesome.

      6. Avatar photo Dear Wendy says:

        The ladies also probably want to know if you’re single.

      7. Avatar photo Addie Pray says:

        i mean, like sure whatever, i guess, ok you can tell us if you’re single, but whatever, i’m breezy.

      8. lets_be_honest says:

        Oh snap Addie. He knows you! I’m sensing a love connection.

      9. Avatar photo Addie Pray says:

        Brian obviously has good taste in movies and used to watch Paper Moon over and over and over again when he was a kid just like I did.

      10. Here’s another secret: I’m blushing.

      11. Avatar photo Addie Pray says:

        By “I’m blushing” do you mean you are single, are between the ages of, say, 30 and 42, love your mother, live in Chicago, like dogs, and enjoy sneaking mini bottles of wine into the movie theater/anywhere really? A friend was asking.

      12. Damn it, there was a no in there (the Chicago one), but your friend sounds amazing.

      13. Avatar photo Dear Wendy says:

        Addie, tell your friend that sometimes you have to venture out of Chicago to find a guy worth dating. I did … and then I married him.

      14. Avatar photo Addie Pray says:

        My friend is awesome! And smart and muy good looking. She said she’d move anywhere for love. So I guess that’s a done deal!

  9. Laura Hope says:

    Every once in a while I’ll look up and see my husband staring at me and I’ll say “what”? He’ll say, I’m sorry, I was trying to picture you naked. PS. We are SO not newlyweds. So I don’t think it ever gets old.

    1. lets_be_honest says:

      That’s really cute.

      1. lets_be_honest says:

        The more I think about this, its been years and years with my boyfriend and I definitely still look at him as super, super hot which I guess is a good thing. He doesn’t age though, so there’s that. I, on the other hand, am very good at aging.

    2. my husband was so excited he could see my nipples through my shirt the other day. I was like, really? So it still works 10 years later.

  10. Avatar photo bittergaymark says:

    I depends on how good the two truly are at sexting…

    But if the two truly NEVER meet in person, then there is nothing real to get in the way or thus be boring… Never meet up? Then it ALL stays one big fantasy. Nobody has real life flaws in a fantasy. People remain who you most want them to be. It is all truly a vivid ongoing projection of your thoughts and desires. Fantasies… They can burn hot and bright — forever. They can last a lifetime.

  11. My only quibble with this (hilarious) advice is, the “worst thing that can happen” in a sexting situation is not just plain nothing, but that those photos/videos will find their way to unintended recipients. Even if the sextee has no malicious intent against the sexter, why *shouldn’t* s/he pass on photos from a totally not-serious, no-feelings, faraway e-fling?

    …says the woman who is paranoid that the sexy photos she took & shared back in her carefree college days will one day resurface in a less-than-flattering context

    1. Avatar photo bittergaymark says:

      There is so much professionally produced porn on the internet it’s MINDBLOWING. Unless you are SUPERHOT — or the photos are somehow wildly extreme or unique — the odds of it ever coming back to haunt you are nil.

      One of my biggest regrets is NOT ever having naked pics of me shot when I was actually still young snd hot. A photographer lover of mine wanted to shoot me naked against the gleaming rocks and phallic saguaros of the Arizona Desert. But I couldn’t do that. I wouldn ‘t do that. Especially since I was destined for fame and fortune as a writer.


      Double idiot. Not only do I regret not having those pictures. (His work was black and white and STUNNING…) But in our sex tape society said pics would have only BOOSTED my big career had it ever come to pass…

      1. lets_be_honest says:

        Idk, with websites devoted solely to posting nude pics/videos of your exes, I think it is something to worry about.

      2. Avatar photo bittergaymark says:

        Some people LOVE to worry… What are the odds of somebody you know ir truly care about perusing such a site?

      3. lets_be_honest says:

        Haha, I’m a professional worrier.

      4. The only reason it crosses my mind at all is that I’m about to go into business on my own and my name is going to become a lot more public when I do. Last thing I want is for someone to Google me and some random photo from 5 years ago that has my name in the filename or metadata to come up in the results because some d-bag posted it on a forum way back when and forgot all about it.

      5. “Paranoia” indicates an irrational fear. I know it’s unlikely that the photos will ever come back, but the possibility still exists and that’s enough to make me a bit uneasy and regretful of ever sharing them.
        One of the flings in which these photos were involved ended in spectacularly messy fashion and I was definitely nervous for the first year or two afterwards when drama still lingered, that the recipient would use them to his advantage. That threat is pretty much gone now, but it makes me inclined to recommend against being too cavalier about sharing photos.

        Bear took up photography for a hot second a few years ago and has some really nice B&W photos of me when I was thinner and had longer hair, but they weren’t nearly as risque as the photos mentioned above.

      6. Yeah, I’m with you, BGM (I mean, obviously everyone has the right to be as paranoid as they want, but my thoughts on the subject are aligned with yours. Like, even if a nude photo DOES surface on the internet. ..it’s the internet, a million other nude photos will bury it)

      7. Painted_lady says:

        I don’t have that luxury. I just don’t. It’s not something that will just be embarrassing and require explanation, I will lose my fucking job and probably have a really hard time finding another. There are actually a couple of articles about revenge porn where the victims were hacked and the pictures were sent to the employer and all of the victims contacts. One kindergarten teacher in my state got fired and hasn’t found another job.

      8. For sure, in certain jobs, you don’t have the luxury of even RISKING it, but I was just talking about my personal views (which are obviously influenced by the fact that I have no ambitions on being a state/federal employee).

        I’m hoping in about 50 years or so, the repurcussions for nude photos won’t be as severe? Because it’s ridiculous to me that someone could lose their job over being naked on the internet. I know other people disagree, but I don’t see any merit in the arguments people make ( i.e. “role model” etc. I can’t really elaborate well right now)

      9. lets_be_honest says:

        I’m trying to imagine my reaction if Lil’s teacher had nude pictures on a website. I don’t think I’d care unless the kids knew and looked for it. And then, frankly, its just time for a discussion with my kid. If she was previously a porn star or something though, I could see having an issue with that.

      10. Avatar photo iwannatalktosampson says:

        Similar to this discussion but not related (I’m not sure why I’m replying to you lbh) there is a video of me WASTED-FACED, like full blown blacked out, in college beating up a boy. I was in a mini skirt and a swimsuit, and it was not in my skinnier days, and like I said WASTED. To this day I cringe thinking about the fact that I can never enter politics or any type of job where there could be a thorough background investigation. Also, in case it matters, I won the fight.

      11. YES. A nude photo of you exists somewhere on the internet, so…. you are somehow less qualified to do your job? If you work for a religious organization, that’s one thing. If it’s porn, and you teach kids, that’s debatable. But documentation that you were naked once? GET A GRIP, PEOPLE.

      12. Painted_lady says:

        It’s beyond fucked up. I work in a pretty reasonable district that acknowledges that I’m an adult – other districts I know of have fired teachers for having Facebook profile pictures of them holding a glass of wine. It’s insane – I don’t understand how we cater to the craziest, most conservative section of the population rather than go, “Hey, calm the fuck down, unless they’re involving your child directly, NONE OF YOUR FUCKING BUSINESS.”

        On top of all of that is the fact that this kindergarten teacher I know about who was fired was treated like a criminal rather than a victim as her property was stolen and she was put in a sexualized position without her knowledge or consent.

      13. lets_be_honest says:

        Do they provide you with rules prior to taking the job? Are there guidelines anywhere that warn you of this before you join on?

      14. Painted_lady says:

        Kind of. I don’t remember the exact wording in mine, but most handbooks say something to the effect of, “Maintain professional manner at all times.” And in my orientation, they basically said something to the effect of, “Hey, here’s some really good examples of situations where it applies that you might not have thought of…” And it was basically if you open yourself up to a situation where a student might see you being unprofessional, at school, in public, online, whatever, it *can* apply. Again, the district I work for applies reasonable expectations of privacy, which means as long as I don’t make direct contact with a student and make attempts to keep my private life private, then I’m safe in that respect. I’m also terribly conscientious; derby formal used to be held at an 18+ venue down the street from my apartment, and when we had to change venues this year, I asked that if we were keeping it in town, that we change to a 21+ club because I was so scared to run into a student last year, I couldn’t enjoy myself once they opened up our private room and ultimately went home early.

      15. Yeah, the possible ramifications for teachers are insane.

      16. I think we’ve talked about this and I feel the same way. I can’t imagine anyone actually caring enough for it to “go viral.” Maybe some people I know “irl” would be all “omg” but I’m sure it would blow over pretty quickly and be “nbd”. Plus, the pics I would share in a sexting scenario are relatively flattering and don’t show my face. You know?

        (And in general, I tend to think – it’s just nudity. it’s just sex. Get over it.)

      17. AliceInDairyland says:

        This has inspired me to get on the “making sex-ay pictures” train. You’re only 23 once!

    2. Avatar photo GatorGirl says:

      I’m with you. My abusive and crazy ex does have some nudes and it is a little uncomfortable. It has crossed my mind that he is crazy enough to send the photo’s to say an employer or my mom, or perhaps slap them on facebook. It’s unlikely that there would be a huge long lasting effect on my life, but it would still be a very difficult thing to go through.

      1. Avatar photo bittergaymark says:

        The problem then isn’t so much the naked pictures — but that you dated a psychopath…

      2. Avatar photo GatorGirl says:

        Doesn’t everyone date a crazy person at least once in their life?

      3. lets_be_honest says:

        Or at least someone that turned crazy maybe? haha

      4. Avatar photo GatorGirl says:

        Yes, or someone that becomes nuts? IDK, I’m sure plenty of “sane” people have felt vindictive and done shitty things (like send naked pictures to an employer).

      5. lets_be_honest says:

        That too, yes. So…we’ve now summed up that essentially every single person MIGHT send those naked pictures you took. We’re all fucked! (I have none, which may be more sad than anything)

      6. Avatar photo GatorGirl says:

        Hahaha. You have never sent a naked picture? Spice it up lady! Go send peter a boob shot from the bathroom or something!

      7. lets_be_honest says:

        Ha! So Peter is…different. I sent him a cleav shot ONCE and he nearly lost his mind with worry about someone else seeing it. Don’t ask. He can be strange. He also works in “tech” so I guess might be more aware of things? My vote is on weirdo though.

      8. lets_be_honest says:

        Oh, and before him there just wasn’t anyone to send to I guess. My teen years were before sexting existed.

      9. Avatar photo GatorGirl says:

        Hahahaha. We where long distance for 3 years, so boob shots basically sustained us. It doesn’t happen now, so I don’t think he’s a total weird-o. I was in college in that like magical bubble where we all had the technology, but no one realized it could totally screw you- so we did what ever. FB was for college students only, and we’d put all kinds of obnoxious shit on it, because only our friends could see it! (so we thought!) Now I’m much more careful with pictures.

      10. I love sexting. And I discovered the other day that my phone can do front-facing video (like you can see the video as it’s taking) & then I downloaded an app that edits video (to crop those awkward beginning & end parts where I’m turning pressing record/stop). Fabello is down with it, but I think he thinks I’m a nutcase sometimes. Anyway, my point is that sexting is fun!! You should do it @LBH. If Peter isn’t down, just sext me 😉

      11. lets_be_honest says:

        Haha, Fab. 🙂

      12. Avatar photo GatorGirl says:

        Fab, you’re nuts! (in a fun way!)

      13. Avatar photo GatorGirl says:

        Fab, you’re nuts! (in a fun way!)

      14. Avatar photo bittergaymark says:

        I’ve had relationships end badly — but nobody has ever been hell bent on destroying my life. Hmmmm, maybe they just didn’t care enough.

      15. Avatar photo Addie Pray says:

        Maybe their mission was to just make you really really bitter?

        Truth: Mark, in real life, you are Mr. Optimistic, aren’t you? (Wait, what’s the opposite of bitter?)

  12. Prudy McPrude here…how is this a good idea? I don’t see why someone would ONLY interact via sext and never meet each other. Fantasies and whatever sure, but wouldn’t that close someone off to potential real relationships in the area instead of some fantasy all the way across the country? If I met a potential boyfriend and found out he had been sexting someone across the country for any period of time, I would most likely just move on. But again, I’m Prudy McPrude so that probably has something to do with it.

    1. lets_be_honest says:

      I’d be pretty shocked if someone you started dating told you that.

    2. I don’t see how it would close someone off to a real relationship. It’s basically just porn.

    3. yeah i think it is just a fantasy for that person. something fun, similar to porn like rachel said that someone might do. i don’t think it would close them off to a real relationship. unless they were unhealthily attached to it or preferred it to a real relationship.

    4. What if they were sexting someone NOT across the country? 😉

  13. Drew is hilarious!

    Reading Brian’s response, though, made me think of the droves of people we hear about who think they’re in a relationship with someone they’ve never met. So, never underestimate someone’s ability to “miss” someone they only know through sexts. That’s not to say it’s normal, but to me, someone who writes in asking about this might be one of those folks.

  14. My first time here. This is such an intelligent, friendly, and oddly applicable thread. The alliteration was top-notch!
    To the person concerned about the pictures resurfacing:
    I have fears of my loss of privacy, especially since sending explicit content this last year, and need to step up file management and basic privacy settings. As a recovering chronic worrier, however, I limit my concern to my family seeing anything from my own devices. Beyond home, I’d like to think I’d be glad I didn’t worry all the time–I clearly managed to have a great time–and in a compelling connection. We met 2.5 yrs ago, but have had no IRL since. When I try end it, I wrestle with the palpable loss for months until he comes back around.
    At 50, I don’t yet regret a connection to something/someone that brings such an exquisite and unusual joy. It wouldn’t be a fair trade to lose in exchange for the hope of acceptance of orhers–who are likely obedient to the privacy robbing culture that judges the content it steals.

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