Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s anonymous mailbag Tuesday and I am writing this mailbag quickly because I’ve got three boys jumping on the bed begging me to take them to the swimming pool. So if there are even more errors in this mailbag than normal, that’s the reason why. 

Blame my kids. 

Send your anonymous mailbag questions to, anonymity guaranteed

Here we go:

“I’m a 28 year old doctoral student dating a 29 year old really hot almost lawyer (she takes the bar in February). We’ve been dating over two years so there’s some natural pressure (100% from her and her family) to get married soon. Neither of us is really in the best financial situation currently and neither family can really afford to put on a wedding. Doing some at-work googling, I discovered a webpage when either of our names is searched dedicated to our wedding date two years in advance. I’m not even sure I’d like to be married now much less have a webpage that’s the fourth link down on our names when googled. What the hell do I do?”

I think you have to confront her about this webpage because it’s very controlling behavior on her part if she’s 100% behind it. It’s not controlling that she may have a wedding date picked out — tons of women do this — or even, to be honest, that she has a venue picked out, but to actually build the website and have it discoverable on Google when your names are searched? Wow. 

Both of you are going to be looking for professional jobs soon. It’s totally possible that someone will be contemplating hiring you and end up on this webpage. That’s strange. Imagine how weird it would be for you if someone else had found this website before you did? (There are tons of Outkick readers Googling their boyfriend and girlfriend’s names right now, by the way, to see if this happens for them.) 

My bet here is that she isn’t aware that the website is public and she will be mortified if you mention it to her. That or she hasn’t even done the website herself and it is her mom’s work. If her mom did it then moms never have any idea how technology works so your future mother-in-law would definitely not be aware of it being public.

Lots of you have proposed to your girlfriends and then within like two days your wedding date is set and it’s already booked for a venue. Most men are clueless about things like this, but that shit doesn’t happen by accident, your fiancee and her mom have been planning all these details in advance. They planned on you asking her so they could have everything set and ready to go the moment they got the official go ahead. It’s like wedding Nascar. 

So my bet here is that your fiancee and her mom have been planning her eventual wedding day — and maybe even venue shopping — and this website is the result of those conversations. 

But no matter how it happens you definitely have to bring it up with your fiancee and see what her reaction and/or explanation is.

Hope she’s really hot because she might be really crazy too. (And smart crazy too if she’s going to be a lawyer. Good luck with that).  

“I’ve made the following offer to my husband: if he will relocate to the beach I will give him a blow job or sex every single day, except for 3 weeks of the year, at my discretion. (This would cover me or him traveling solo or if I get the flu.) That would be 344 days out of 365 that he is guaranteed to have an orgasm in 2017.

We currently live in northeast Tennessee, where he grew up and about an hour from where I grew up. We live in his hometown where I attended college. A lot of my friends have moved away and many of his have as well. I have wanted to live at the beach since I was a little girl and am over living in this town. Obviously, because the South is amazing, I’d like to live at a Southern beach. However, I’m happy to live anywhere warm and near a beach. My husband has worked his way up in sales and is in management. The company he works for has numerous stores in Florida. He claims his main concern is finances but he could have a comparable opportunity if he would pursue his job in a different market. 

Please tell him this is the deal of a lifetime.

P.S. My other thought is to cut off sex and oral sex until he will move.”

Ah, the proverbial carrot and the stick approach to negotiation. Except it is being deployed here as many women have deployed it throughout the centuries to get their husbands to do something: the proverbial more pussy or no pussy dilemma. 

First, this is the deal of a lifetime for your husband. He gets virtually unlimited sex and moves to a more desirable place to live. (East Tennessee is fine, but a Florida beach is tough to beat.) 

Hell, there are married men reading this right now that haven’t ever had sex 344 times with their wives and they may have been married five years or more.

Your husband needs to make this deal, but I wouldn’t advise you cutting off sex to force him to make the move. Being bullied with threats of pussy withdrawal is likely to provoke sore feelings. You want him to be happy to move, not move out of anger.   

“I’m an active duty Marine stationed at Camp Pendleton. I place some of my wagers through a small time bookie I met through a mutual friend and everything has worked without a hitch. Until last week. Last week I hit it big (for a poor person) and won $2700. But now the bookie is ducking and dodging me and won’t give me my cash.

Here’s the problem. A while back I hooked up with his smoking hot girlfriend and my now fiancee does not know that this happened. At the time he didn’t know my fiancee so he didn’t rat me out but he does now and knows we’ve since gotten engaged. Sure I can go to his house and beat his fucking head in but if I do I’m sure he’s gonna call my fiancee and let her know what I did. To make matters worse my fiancee forbade me to place any bets until after the holidays. What’s my play here? This is a substantial amount of money by my standards and that money buys me a plane ticket to Ohio to spend Christmas with my two sons and fiancee and also makes sure I am able to get them the gifts that I want to get them. That is essentially what this cock bag is taking away from me so I cannot just cut my losses and let it go. I HAVE to get some kind of satisfaction out of this. Hell I’m to the point where I’m willing to track him down and negotiate to at least give me some of my damn money and cut the rest as a loss. But if he refuses and tells me to fuck off I may lose my shit.”

Well, it’s now after Christmas so hopefully you got your money. But if not I think what you have to do is tell him to give you half your money right now and you’ll keep the rest gambling with him on credit. That way you get $1350 in cash, but you keep some credit with him which allows him to handle a cash shortage.

You probably already know this, but based on his refusal to pay you in an upfront manner, you can never wager substantial sums of money with him again.

Whatever you do, don’t physically threaten him or beat him up. This is a bad, bad move on your part since it could cost you your fiancee and get you put in jail. 

And if you’re in jail then you can’t read Outkick or listen or watch Outkick and that’s bad for me. 

Also, honest question, why would you use a bookie when there are so many offshore gambling sites that are easy to bet with and don’t require you to ever deal with a shady ass bookie?

Both are equally illegal.

I’m just curious.  

“Recently, my wife and I took our two year old son to Magic Kingdom. As we were in line waiting to see Winnie the Pooh and Tigger with our two year old, I got more and more frustrated by how long the line took. We were probably 25 people deep, but it took us over 45 minutes to get to the front of the line. During these 45 minutes, I watched countless adults (many without kids of their own) freak out when they got to the front of the line. They were more excited to meet Pooh and Tigger than a ten year old boy was after he saw his first pair of tits. I started to yell out to these adults that they are not real, but rather someone dressed in a Halloween costume. I was also asking people if they freak out when they see Santa or the Easter Bunny at the mall. No one answered me. Needless to say I did not make any friends that day. Not only did they freak out when they met the characters but also when they got their autograph. I mean it was like seeing a ten year old Boston boy getting Tom Brady’s autograph. It was unbelievable to me.

My question is, at what age is it unacceptable to freak out when you see a character at Disney? Or am I just a bigger asshole than I originally thought? Am I being racist towards Disney characters?”

Now that I have kids I don’t believe that adults should be able to visit Disney World without kids during the daylight hours. 

That’s right, in my ideal world adults without kids would only be able to go to Disney World from the hours of eight to midnight. 

That’s it. 

Disney World has gotten too crowded otherwise. 

This might sound like a crazy idea, but Legoland requires you to have kids to attend and it’s fabulous. The result is that the park isn’t insanely crowded, the kids can all ride the rides without standing in line for an entire day, and you don’t have creepy ass adults standing in line to get Disney character autographs. Seriously, what kind of grown person does this? I wouldn’t yell out that the characters were fake like you did, but I definitely understand why you were so upset to have to wait with your two year old so some adults could get their pictures taken with a costume character. 

I’m taking my kids to Disney World in February and I’ll inevitably be trying to ride “It’s a Small World,” with them or Snow White or Peter Pan and it will be swarmed with adults in line in front of us. Just adults, without any kids at all. What the fuck, adults, all the places on earth you could go on vacation and you go to Disney World just to make the day that much more miserable for those of us with kids than it otherwise would have been?

Get out of the park and leave it to those of us with kids.

One day you will have kids too and you will know what it feels like when your two year old loses his or her mind and refuses to get up from the ground outside the goddamn teapots no matter what you do. And when you pick up the kid and the kid does that rigor mortis dead body both arms out and both legs extended at the same time thing so it’s like you’re suddenly carrying an ironing board and you have no idea what to do with them. I’m telling you that moment is coming for you adults without kids at Disney World too and it will be awful and drive you insane and you will hate all the people without kids who are standing in front of you in line giggling about meeting Winnie the Fucking Pooh. 

So get out of my park. 


“I work for a large (multi-billion dollar) engineering firm. One of the perks is we have a very nice gym/fitness facility on site. So I’m in the gym changeroom the other day after an intense lunch-hour workout, when the VP who oversees my department walks in. I’m currently leading a multi-year R & D project and typically already meet with this VP once or twice a month to give him an update.

So anyway, he grabs the locker next to mine and starts to get changed, then turns to me and asks for an update on my project. I’m dripping with sweat, shirtless and just about to drop my shorts and head for the shower. But now I have to give this guy a project update in the changeroom while we’re both mostly naked. Awkward, right?

The update goes fine and he heads out, but now I’m kind of kicking myself. I’m a well-hung guy and can say with 99% certainty that I’ve got this guy outclassed….should I have dropped my shorts and given this guy the update while “full-Monty” to show who the real VP should be?”

What if you dropped your pants and thought you had just outdicked the VP and then the VP dropped his pants and he Steve McNair dicked you? (Steve McNair, RIP, has the largest dick in human history for those of you who weren’t aware).

Then you’re trying to give this status update and he’s just over there with his elephant trunk dick just kind of casually standing there about to tip over from dick weight and you just bungle the presentation?

And then this VP takes you off the project and you lose your job all because you thought you had a winning dick hand and then he dickupped you and called your dick and you got McNaired?

So I think you made the right call.

Send your anonymous mailbag questions to

Anonymity guaranteed.  

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.