Anonymous Mailbag

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It’s Tuesday, time for the anonymous mailbag. 

By the way, the anonymous mailbag is such a hit that it’s all readers want to talk about when I see them out. Y’all come up and say, “I love Outkick and the anonymous mailbag is the best thing you’ve ever done.”

I agree. 

That’s thanks to you guys and girls sending in such good questions. As always anonymity is assured and remember, you’re in the trust tree, we don’t judge you. Send your anonymous questions to

Here we go:

“Situation: Girlfriend has been badgering me to take her two-stepping (We live in Dallas) for the better part of 2 months now. I’m an accountant in the throes of busy season so whatever spare time I have, I generally want to use sleeping, eating or watching sports. So as you can imagine, listening to Waylon’s greatest hits while country bros passive aggressively spin their girlfriends around was definitely not high on my priority list. So last night we went two-stepping.

After 4-5 songs, I feel like I’ve earned a beverage. So we step off the dance floor and get a couple overpriced Coors lights and hang out. While we’re standing there, a country bro walks over to me and without any sort of introduction or any other formal social pleasantries, asks me: “Would you mind if I danced with her?”

Now, this guy is 6’3 and looks like Abercrombie’s wet dream in cowboy boots. And I definitely have outkicked my coverage with my GF, so to say I was panicked by this was putting it mildly.

So I do what any alpha male would do if his girlfriend of 2 years was asked to be whisked away by real life Cowboy Casanova….I meekly looked at my girlfriend in helpless desperation and said, “Sure.”

Before I knew it, he was twirling my girlfriend in a fashion I can only describe as 2-step sex. He was literally the best dancer on the floor and easily the best looking guy in the bar. I’m crying on the inside as I think of usernames for my future Tinder account profile.

Fast forward to the end of the song when I think my girlfriend will return to me, instead I see them on the other side conversing as the next jam is played and THEY START GOING AGAIN. At this point my shame is turning to anger. I’m just awkwardly standing off the side of the dance floor with my drink and hers in my hands…..this goes on for 1 more song. So for those counting at home, my girlfriend danced with this random, extremely good looking, stranger for 3 songs while I’m left pretending like I always carry two beverages around and stare at the dance floor.

When she eventually comes back to me, she can clearly tell I’m upset. I’m beyond ready to leave and tell her as such. She THEN GETS MAD AT ME FOR BEING MAD! “Why did you say it was ok to dance if it wasn’t?” she asks. Seriously, what was I supposed to do? “No, you can’t dance with MY woman.” And the more I thought about this, the more I realized this dude is the Danny Ocean of girlfriend incursions.

Anyways, I need reaffirmation from the Gay Muslim: What else could I have done? Was I right to be upset?”

You can’t say no to the guy asking to dance with your girlfriend without looking like a total desperate, overprotective asshole. So your girlfriend — and every girl reading this — can’t play that line. Also, hello, she could have declined to dance with him after you allowed it. That’s easy for her to pull off, “Thanks for asking, but I only want to dance with my boyfriend tonight,” is a perfectly acceptable response by her.

Odds are she was blown away by the hotness and sheer badassedness of this Cowboy Casanova who picked her out of the crowd to dance with and marched right up to you to demand her hand. It was suddenly 1840 in the royal — two stepping — palace and her prince charming — not you — had just arrived on the scene.

Let’s reverse this situation. It’s unlikely to happen, but what if a hot girl was standing next to you guys, saw how good you were at two-stepping, and asked to dance with you for a song. And then you went three songs of two-step sex while your girlfriend stood on the side of the dance floor holding two beers and waiting on you. Do you think she might be upset at you for that? She would be ready to murder you by the time your returned.  

So I think she should have ended it after one song and come back over to you. Three two-step songs is a long time to be standing on the side of the dance floor holding two beers. (Although, am I total degenerate alcoholic? At crowded places like this I always get two beers at a time when I go to the bar. So I don’t think double fisting the beers is that big of a deal. Just drink faster.)  

Now if we brought your girlfriend in front of the anonymous mailbag jury she’d probably say, “I knew you didn’t really want to dance and he was a good dancer so I went ahead and did three songs with him so you wouldn’t have to dance as much. I didn’t think you’d care. I didn’t like him at all, he was just a great dancer.”

She’s lying about that. She won’t ever admit it, but she probably wanted to bang him at the end of that third song.

But in the grand scheme of things, it’s not a big deal. I’d be over it by the time we got home and she had hot make-up sex with me — while she was pretending it was the Cowboy Casanova she was actually screwing. 

“Last July my best friend was newly single after being cheated on by his girlfriend of four years. They broke up several months prior and he had not gotten a single piece of ass since. I think most of it was just the inability to move on, but either way he needed a piece and asked me for help. At the time, I had been banging this hot chick that lives down the road from our lake house. So naturally, I call her up and ask if she has any friends that could lift my buddy’s spirits up in a time of need. The next day she and a friend come over for a day full of drinking and fun on the water. So several whiskey and sprites later and as the sun began to set over the Tennessee horizon, we felt that a boat ride on my new pontoon boat was a great idea.

As we are cruising along the lake, my buddy and his companion for the day climb to the top deck. After a half hour or so, nothing is happening between them. So I look to my girl and advise that we should stop the boat, climb the deck and start fucking in hopes that we would ignite the fire between the two of them. Well, we did just that. Me and my chick are going at it and I’ll be damned, I look over and my buddy is about to start pounding his girl as well. Fifteen minutes in or so, my drunk ass gets a bright idea. I lean up and yell, “switch!” And these chicks were totally cool with it. So here we are in the middle of the lake at dusk, on top of a pontoon, having a big orgy. Not only did I get my buddy his piece of ass, I got him two pieces of ass.

My question is two fold. Was this a ballsy move on my part to signal for the switcheroo or would any other best friend have pulled this off? And should we make this an every summer occurrence or leave it in the past?”

Your call for the switcheroo was incredibly bold. But you could have immediately played it off as a joke if one of the girls had gotten offended by the request. It reminds me of one my favorite lines from the immortal Nelly party anthem, “Hot in Herre” (Yes, the song title actually has an extra r in it, for once this isn’t a typo by me).

You remember: 

“I gotta a friend with a pole in the basement (what?)
I’m just kidding like Jason (oh)
Unless you gon’ do it”

All sexual suggestions that are too forward are jokes. 

Unless you gon’ do it.

Also, fifteen minutes in? If that’s actually true maybe your girl switched just because she thought your buddy on the dry spell would be done faster. 

As for your second question, did you really just ask me if you should have an orgy every summer or not? I’m not an expert on life advice, but if the question is, “Should you have an orgy or not?” how many single guys are ever answering this no?

Of course you have an orgy.  


I work in a very public industry, similar to one of the jobs you now have.

Here’s my problem:

I have a co-worker who is getting a promotion and will be in the public eye pretty soon. A few months ago, I was googling her name to double check the spelling of her last name because I needed to add her to a list I was submitting.

The top hit that comes up is from an old photo storage account. It’s clearly at least 5 years old, but her profile picture is probably not something she wants out there anymore. (It’s her topless with a friend and their boobs are pressed together. You can’t see any nipple…but plenty of sideboobage).

Being a gay muslim and all, what do you suggest? Do I tell her, and have our future interactions at work be awkward because she knows I’ve seen it? Or do I play dumb, and hope someone doesn’t find it and post it on a blog of some sort causing even more embarrassment for her?”

If it’s truly the top Google result for her name, she has to know it’s there and I don’t think it’s awkward for you to mention it. It would be awkward to mention it to her if it were on the 14th page of Google results or the 19th page of her Instagram photos, but the first page of Google is something that anyone could easily find. Tell her you came across it and — in a non-threatening and non-creepy way — just tell her that in her new job she’s probably going to have people searching her out online and she might want to manage her online profile a bit and make some pictures and social media accounts private. 

Having said that, is sideboob really that big of a deal in this day and age?Every hot girl under thirty has an Instagram account with pictures of them looking hot on it. Many of them are wearing hardly any clothes in these pictures. As a result, every guy reading this right now has, at some point, found himself falling into an Alice in Wonderland-like Instagram hole. You go on there because one of your buddies sent you a picture of a hot chick’s newest picture and the next thing you know it’s a half hour later and you’re still clicking on new pictures and you have no idea where the time went.

Going on Instagram to look at one picture is like trying to eat one Cool Ranch Dorito, it’s impossible to pull off.  

“I think I messed up. My fiancee is making a wedding website, and she wanted me to write a paragraph about how we met, our proposal, why I’m friends with all my groomsmen, etc.

Of course instead of just doing this, I opened my mouth and had to tell her that I just didn’t care about a wedding website. This led to a fight about me not being involved in planning and not caring about the wedding.

Now I realize to just do as I’m told with the planning, but she’s still upset with me. My question is two fold:

1) Will I ever get out of this doghouse? How can I help expedite this?
2) Am I wrong in thinking a wedding website is the stupidest thing possible? I mean, who’s visiting besides the couple, close friends, and family who already know all of that?”

1. You’re about to get married — you will never really leave the doghouse for the rest of your life. 

You might as well get used to it.

2. No, you are 100% correct, all wedding websites are stupid.

You’ve learned an important lesson about wedding planning, do as you’re told and keep your mouth shut.  

Last week’s mailbag about getting banged in the ass by a woman while she wore a dildo produced a torrential downpour of responses from both men and women. I have selected two to feature, one from a woman and one from a man:

“Please keep me anonymous since my fiance has friends in law school who read your mailbag.

I just wanted to respond to the latest anonymous mailbag (an awesome part of my Tuesday by the way). I have had several guys ask me to fuck them with a dildo. I declined. As you can imagine I was completely shocked by the first guy and we broke up soon after. After the second guy asked, I just thought it was a weird curiosity that some guys have. In total I’ve had 4 guys ask for this. So, in my experience, this is a desire that goes both ways. As a woman, I can’t imagine the appeal on our end, but I can kind of see why the guy might want this. Of course, I live in the south, they may just be gay and afraid to come out. I am no longer with any of these guys but as far as I know they are still practicing heterosexuals. Maybe I just attract a super specific kind of freak (our sex lives were normal otherwise).”

The number of people who wrote saying they’ve done this or been asked to do this blew me away.

Really, it did. 

“I have been following you since your CBS Sportsline days. While she never proposed blow jobs for a year, my wife wanted to know how it felt to give it as she took it. As a married straight man, having my wife ask me to “bend over” a few years ago was a shock. Since we have been together for almost twenty years, and she has been receptive to many things, I gave in. That first time was an eye opener. The simultaneous BLOW JOB with the dildo in my ass was mind blowing to say the least. It has only happened one time since, but if you haven’t had it, you do not know what you are missing. Gay, Muslim, Hetero, Baptist…, there is nothing to be ashamed of. It feels incredible.”

And there you have it. 

Another incredible week of the anonymous mailbag. 

Send your questions to

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.