Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, you can send your anonymous mailbag questions — which, in the interests of your anonymity, are immediately deleted as soon as I cut and paste them into the mailbag — to

With that in mind, we begin with a question from several of you. 

“I had an Ashley Madison profile. 

Should I come clean in the event the hacking starts or keep quiet and hope I’m not caught?”

If you’re married and you have a Tinder profile or an Ashley Madison profile or a Grindr profile or whatever kind of public profile there is to try and meet men or women online to sleep with, I think you’re crazy. I mean, you’re just totally playing with fire here.

(As an aside, I’ve heard the number of married pro athletes with Tinder profiles would blow your mind. Seriously, how dumb are you to do this in this era of the Internet? Hell, Gawker just blew up a random guy for trying to hook up with an escort and he wasn’t even famous. Of course, it’s also possible that these athletes are so dumb they haven’t even thought of the possibility of getting caught and aren’t aware of what they’re risking. Additional option — your wife just doesn’t care and is totally fine with you having random sex with random girls all over the country. Anyway, every married guy is kicking the under side of his desk right now at work, furious that he’s not a pro athlete with a wife who doesn’t care who he sleeps with). 

Having said that, the number of Outkick readers with Ashley Madison profiles is simultaneously unsurprising and terrifying. 

If you’re not famous, I’d keep quiet and delete your profile and all of your pictures — surely you don’t have pictures up with your face in them, right? If you’re famous, you’re screwed. Because the hackers are totally exposing you.

“I am getting married to my beautiful fiancee in few months, really outkicked the coverage with her, and I need your advice. The wedding planning is going as normal, where she is doing all of it, asks my opinion, and I just nod my head yes in agreeance of whatever she wants to do.

The other day we were discussing about what song we want played for our first dance and she tells me that since she is planning everything else for the wedding that she wants me to take on the responsibility of picking out the song for the first dance and “surprise” her. I am really uncomfortable being put in charge of this decision as we really don’t have a song that is our song and I told her that I would rather us both pick out the song together.

Is this normal for the bride to do? I feel like this could really come back to bite me in the ass if I do not pick the right song and all of a sudden the marriage starts out on a bad note. Since she has made up her mind that I have to be the one to pick the song, what is the best route to make sure that I don’t royally fuck this up? Ask her family and friends for recommendations? Ask my family and friends? Do you have any suggestions? Only a Big, Gay Muslim can help me out with this predicament.”

You’ve got to go with “Ignition” by R. Kelly.

Either that or “Magic Stick” by 50 cent.

Tell me you wouldn’t lose it if the bride and groom were standing out there arm in arm prepared to dance and you heard the opening chords of “Magic Stick.”  

More seriously, I have no idea which song would be perfect to pick. I don’t even remember what our first dance was. I didn’t decide anything about my own wedding. I barely even knew what state it was in. The only thing I had to do was get my hair cut and I even screwed that up and got an awful bowl cut the day before we got married.

Anyway, I just left writing the mailbag to ask my wife if she remembered our first song and she said she didn’t remember it either. So there you go, it was an incredibly memorable dance. 

My wife also suggested you pick, “Any crappy Ed Sheeran song,” as your first dance. 

So I’d go with “Magic Stick.”

Please, for us. 

“Well, here goes nothing. So my wife brought up the idea of swinging. Always together, same room type stuff. This would include threesomes etc. So we signed up for a pay website and are currently seeking out other couples and females who we think are hot. We are 2 weeks in and to this point we have not done anything yet.

Am I crazy for doing this? What things should I be thinking of and considering? What percentage of married guys like myself would do this if their wife wanted to? To me I think it is very high; say 70% or so. We live in Nebraska and on the site we signed up for there are pages and pages of swinger couples on it. I was shocked at the amount and the fact there are so many good looking people on it. What’s your advice?”

First, if there are actual single women who are interested in threesomes with married couples and your wife is fine with it, why the hell wouldn’t you do this? I just have my doubts that single, hot women who want to be in threesomes with married couples need to create online profiles to do it. I feel like you’re going to spend a couple of weeks sending emails to a “hot girl” and then a 53 year old Moldovan man in jean shorts and a tank-top is going to show up at your hotel room.

As for swinging with additional couples, my reticence here would be finding yourselves involved in another couple’s drama. Do you really want any kind of lasting connection with the people you swing with? Wouldn’t you want to never see them again after? Now if you could have an “Eyes Wide Shut” type situation — where you have to post clean STD records to enter the party — and then have a smoking hot orgy party where everyone wears masks and you never have to see any of those people again, that seems ideal to me. I can’t imagine very many married guys saying no to this. And I think with alcohol quite a few women would be fine with that too.  

I also have no idea how many married people actually swing. But I’m fairly confident if a famous athlete or coach went public as a swinger that ESPN would have to give them the courage award next year.

I’d love to know the percentages who swing. Five percent? Ten? Lower? Seriously, I have no idea. But of those that do swing, how many of them look decent naked? Let’s be honest, most married people don’t look very good naked. For instance, I don’t think Charlotte McKinney is going to get married and be a swinger one day.

But if there are any anonymous Outkick swingers with insanely funny swinging stories — there have to be a bunch, right, the entire thing is steeped in awkwardness — then we definitely need those emails for the anonymous mailbag. 

“First of all, count us as a couple who missed the anonymous mailbag while you were on vacation (although we are convinced it was a pilgrimage to Mecca). Last week’s questions about how many people have the mailbag read to them grabbed OUR attention.

A detail here- I’m a 25 year old graduate from an SEC school. My SO is over 40 and…married. (No, we did not meet on Tinder, and I don’t think he will ever think about making me take a polygraph after reading the mailbag.)

Last week’s reader has Siri read the mailbag to him and wondered who else has it read aloud. I am also too busy to read much; therefore, my married “boyfriend” reads it to me every Tuesday afternoon between sessions in the sack. He has done this for many, many months. I wish I were kidding. We have shared many a laugh and many more a cringe over people’s sick stories and your poignant replies. It’s practically a staple in our relationship! I don’t know if I like listening to it as much as he likes reading it aloud since he won’t even let me read it over his naked shoulder. Something about a “cold read.”

My question: is there anyone else that uses the mailbag as erotic literature? And as an aside-what is getting my man “back up”? Is it my naked body writhing all over him or…the MAILBAG?!”

I hope it’s your naked body. But I wouldn’t judge anyone for using the mailbag as erotica — not even a 25 year old SEC grad sleeping with a 40 year old married man — but I would think there are much hotter stories on the Internet than on our mailbag.  

Speaking of erotica, I was talking with a buddy recently about things that we’d love to see on TV. And I came up with a jerk off meter. You know how on Periscope it shows you exactly how many people are online at a given time watching a Periscope broadcast? What if you could add a jerk off meter to the right corner of your television to see how many people are jerking off at that exact time while watching any given show?

Tell me this wouldn’t be incredibly addictive.

For instance, how many people jerked off to the “Game of Thrones” scene where Daenerys climbed on the dragon and flew away? To Sci Fi nerds that’s like the threesome scene in “Wild Things.”

What about a random college football game? Women’s volleyball at two in the morning on the Longhorn Network? The jerk off meter would be so addictive.

In fact, we’d probably just post jerk off meter stories on here. Between that and people getting attacked by sharks, we wouldn’t have to do anything else to get five million people a month reading.  

“My 24 year old roommate is a good looking guy who can get girls fairly easily. While out last weekend he met a single mom, A HOT MOM, but nonetheless a mom. We’ve been debating this issue for days now. Does he take her out and risk falling for an incredibly hot mom or avoid the situation all together and continue in pursuit of hot women who are without child? Being a fan of moms myself I’m all for him taking her out, but some of our other friends see it differently saying he doesn’t want that kind of responsibility or she’ll come with too much baggage.”

Here’s an important question worth considering — what does she want? If she’s a single mom, she may hate men right now and not want anything serious. She’s got a young kid and whatever man she had it with hasn’t been a very good partner. So the last thing she may want in her life right now may well be a serious boyfriend. 

If she wants you to be involved with the kid’s life the moment you start dating, that’s a huge red flag to me. If I were a single parent there’s no way I’d bring any dating partners around my young kids until I was really sure they were going to be a significant part of my life. It’s not fair to the kids otherwise.  

So while I’ve never dated someone with kids, as a parent of three, I don’t think the initial aspects of dating her would be that much different than dating someone without a kid. Except, you know, you have to actually date. You can’t just text her at two in the morning to see where she is. The answer will be, “Asleep.”

Just like you typically don’t meet someone’s parents until the relationship has reached a decent length of time, I can’t imagine your friend would be involved with the kids very much initially.  But as they continued to date — if they did — I’d think she’d want to see what kind of person he was around kids. But he’d have plenty of time to decide whether he likes her or not. So I wouldn’t eliminate it as out of hand, but I’d understand that there are potentially complexities there that wouldn’t exist for a girl with no kids. 

(I’d also make sure her baby daddy isn’t in jail for murdering an ex-boyfriend. Honestly, I’d be much more worried about him than I would be her or the kid. If you date someone with an ex and a kid you’ve got to understand that guy is a part of your life from that point forward).

“I’ve been seeing this girl for about three months, and things are pretty serious. She may be the one. The problem? I’m bi and she doesn’t know it. I’m not, like, 50-50 bi. It’s more like 80% straight and 20% looking for the D. My 20% is almost entirely satisfied with the occasional visit to Manhub or the gay section of YouPorn. (Yeah, 3 or 4 times a year I visit the Men For Men section of Craigslist, but one good encounter lasts me several months. Really.)

Anyway, about a week ago I broke out the iPad and was just starting to indulge my 20% when my girl walks quietly into my living room and saw what was going on. And let’s just say that the audio and visuals left no doubt what was on the iPad. She freaks and yells out, “What the F are you doing?” I quickly shut things down, zipped up, and tried to laugh, stammering, “Just celebrating gay marriage!” (Not funny, I know, but it was shortly after the Supreme Court decision and I was startled.) She walks out without much more talk, and it’s now been a while since I’ve seen her. Our phone calls are strained.

So what do I do? Do I lie and say it was a one-time thing, that I’ve never acted on these urges, and that I won’t do it again? Or do I come clean and say this 20% is a part of me, but that it’s (mostly) just fantasy and being with her is my dream? Complicating matters, she’s from (Southern state) and we’re supposed to meet her parents at the (redacted) game over Labor Day weekend. This needs to get resolved before then.

I really do love her. She’s smart, witty, funny, sweet, in great shape, beautiful, hot, and awesome (and I mean AWESOME) in bed. I don’t want to lose her, but, well, you know…that 20% thing.”

This is where the difference between men and women becomes crystal clear. You always get those incredibly liberal people on the Internet — many of whom Tweet me bitching about what I write — who are like, “The sexes are totally the same, you pig. You’re sexist if you think otherwise.”

Right, of course, men and women are the exact same in all their urges and desires. Only neanderthals would think otherwise.   

So let’s reverse this situation and see how this plays out. You’re a guy and you come home and surprise your girlfriend as she’s plesasuring herself watching lesbian porn. She tearfully confesses to you that she’s mostly straight, but she’s 20% bisexual and hooks up with girls 3-4 times a year.

Every guy reading this right now would think that he had found the hottest girlfriend in the history of humanity.

But unfortunately that’s not our story here.

You’re a dude and your girlfriend saw you jerking off to dudes on porn. That would freak out most women. (Hell, some women would be freaked out if they caught you jerking off to normal porn). Especially because I’d imagine one of the worst fears of women is finding out that their boyfriend or husband is actually gay.

So you have two options here:

1. Talk through what happened and commit to a monogamous relationship while leaving the bisexual part of your life behind. After all, even if you were 100% straight, it’s not like you are going to only be attracted to her for the rest of your life. You’re giving up sex with everyone else for her regardless of your sexual orientation. If she’s the one, that’s a decision that you’d probably have to make at some point anyway, right?

If you truly love her, you can’t hook up with dudes on Craig’s List anymore. (That line of advice is what every woman dreams of.) 

2. If you can’t be monogamous and give up that part of your life, you have to tell her the truth.

You’re in love with her, but you also, occasionally, like to hook up with dudes. 

Then she decides the future of your relationship. 

Good luck

The anonymous mailbag runs every Tuesday on Outkick the Coverage. You can submit your own questions — anonymity guaranteed — to

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.


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