Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday and welcome to the anonymous mailbag, the most consistently entertaining weekly article on the Internet. 

You can email me at and I guarantee total anonymity for your questions. 

If you haven’t already, go check out yesterday’s Outkick the Show on Colin Kaepernick. Hate to brag, but it was perfect. 

Okay, on to the mailbag. 

“So last night while looking for a charger at my parents house, I stumbled across an iPhone on top of my dads desk, when I unplugged it to plug my own phone in, it lit up with a text from “a woman’s name that I didn’t know”, my curiosity got the best of me and his UNLOCKED (seriously so stupid) phone, was a second phone that he has been using to cheat on my mom, with a girl my age, that he is apparently giving an allowance to.

I left the house and made about a 10 second phone call him to tell him I know about his phone. But this is the first I have spoken of to anyone else. I honestly don’t even know what to do here. I can’t bring myself to talk to him, and have no clue how to go on from here. I kind of wish I could make this whole thing disappear, but don’t really know what to do at this point… my mom and siblings, all grown, have no clue and I don’t know if it is right to tell them or not or how to proceed?”

This is a really tough decision, but my advice would be to stay quiet. 

Now let me explain why. 

First, you snooped and uncovered this cheating incident. That is, you definitely violated your dad’s privacy by checking text messages on his cell phone. Now you can argue that you weren’t intending to catch him cheating, but once you picked up his phone and checked his private text messages, you’d undertaken an investigation into his behavior. 

Second, you don’t know what kind of relationship your mom and dad have. What if your mom and dad have an open marriage? All you’re doing by telling your mom about this is potentially blowing up the privacy of their relationship and embarrassing them both. 

Third, your parents are grown ups and so are you and your siblings, what’s to be gained here? Maybe your mom knows or suspects something, but chooses to ignore it because she’s happy with her family life otherwise. Of course, maybe she doesn’t and it’s possible she’d be blindsided completely by it, but what if she isn’t? Then you’ve just put yourself squarely in the middle of your parent’s relationship.

And if she doesn’t know and you’re the one to tell her, does it make you feel better to tell a 65 year old woman that her husband is having an affair with a woman half her age? What options does your mom really have her. Sure, she can divorce him after raising her kids with him her entire life, but does your mom really want to start dating at 65? I just don’t see a positive payoff here in any way.  

So I would counsel keeping quiet and staying out of this situation entirely. 

If, however, you feel you must get involved, you can threaten your dad that if he doesn’t end the relationship you will tell your mom. I’d consider this more of a bluff than anything else — because how will you really know if he ends the relationship? — but it might assuage your guilt for keeping quiet.

Regardless of what your decision is — I would not tell your siblings. There is 100% no reason they should know about this at all.  

“Recently my group of friends got into a discussion of how far are we willing to go for a certain amount of money. One of our members of the group, a recent Alabama graduate and lifelong Alabama fan, said he was willing to get a tattoo of Cam Newton in an Auburn uniform on his ass for $10K.

Mind you he was at the 2010 Iron Bowl when Cam Newton crushed our hopes at another title for this Nick Saban dynasty we are living in. To take it even farther he said he was willing to get all of Auburn’s wins tattooed on his ass for $20K.

This got us thinking. Could we actually start a go fund me to raise this money and see our buddy go through with this? To put this into perspective for you this would be like you getting a tattoo of Jack Daniels or Lena Dunham on your ass. So I ask you know-er of all things besides the pants industry. How far are you willing to go to get a tattoo of your arch nemesis?”

I’m anti-tattoo so it would take an insane amount of money for me to be willing to get any tattoo at all. 

But I’m more intrigued by your buddy here. 

If I pay this guy $8k will he allow me to Periscope and Facebook Live him getting the Cam Newton tattoo on his ass during Outkick the Show?  

If so, I’m in, email me so we can set up the details. 

“My wife took me to New Orleans for a four day trip to celebrate my birthday. A lot of fun but she is not much of a night owl so mostly great food and in for the night by 10. After we settled in one night, I randomly showed her a picture of your orange Auburn pants. We are alums and asked I her what she would think if I wore them.

She knows I would never be caught dead in a pair of orange pants, and subsequently responded that she would give me a blow job if I wore them. Since she delivers on almost every promise or bet ever, I was immediately thinking jackpot for me and twenty bucks for Clay. However I figured I would confirm the agreement and lock in the promise before I shelled out $20, so I asked if it was for one wear or every time I wore the pants? Her response “every time you wear them”.

That is infinite blowjobs as long as I can stomach wearing bright orange pants, which is completely against my nature. Needless to say the pants were ordered within ten minutes and I am hoping they make it to me by the game this weekend. Clemson is going to crush us but it could be a win for me if the shipment gets to me in time. Back to the investment, $20 and wearing orange pants for infinite Bjs has to be a better investment than Twitter stock. What are your thoughts? To top it off, I was on the same flight as you to Vegas for March madness and decided to follow all your bets for the first two days. I finished up well over $20 which means my investment in the pants is actually $0. How big of a jackpot did I just stumble across?”

See, if you buy Outkick pants, you get blow jobs, that’s how sexy they are. (Also, I think this is how much women don’t trust what their husbands or boyfriends wear to football games. Think about how much effort and energy women put into their average gameday in the South and then compare it with me. We’re savages.)

And the pants only cost $20. $20! 

This explains how we’ve virtually sold out of the UT pants and the Auburn pants are going fast too. 

Better get yours.

“We are one week into college and my freshman roommate’s girlfriend — who is a seniorin high school — is insane. Let me explain. I knew she was a little controlling heading into the year, but it is at the point that I need your help.

Here is a text that he got the other night from his girlfriend:

“Do you go out to eat with girls? Do you see girls often? You said when you’re just walking around the guys “introduce and what not” so does that mean you guys are walking around with girls? Are you spending time with them outside when they are walking around and drinking? You told me soooo many fucking times that you are gonna let me know every second you’re with a girl or talking to a girl and you haven’t. I’m really mad at you right now.”

He gets messages like this all the time. If he doesn’t respond she answers by saying that he must not love her. In my mind he must love her because he has put up with all of this for so long. Just one week into school he has a decision to make, so I ask you, what does he do? Break up with her immediately? Try to salvage the relationship? And if he does break up with her, it being a long distance relationship and all, how should he do it? Thanks for your gay-muslim minority all knowing wisdom.”

He should break up with her the next time he’s home. 

Do it in person and blame it entirely on going away to college and it being unfair to both of them to keep up a long distance relationship. That’s the truth and it’s more fair than letting her drive herself insane with insecurity over his every waking moment on campus. 

Long distance relationships in college typically don’t make that much sense, but I think they make even less sense when it’s so easy to get in touch and one or both of the parties is insecure, which typically happens with young love. She can text him and FaceTime him all day. It’s impossible for her not to think about what he’s doing all day when she’s left behind in high school.

She’s loaded with insecurity, which is a perfectly normal thing for a 17 year old who is still in high school. and thinking about her boyfriend all the time, who is now in college surrounded by girls everywhere he goes.  

It’s not good for either of them and modern technology makes her neediness even worse. At least back in the day when she would call his dorm room it would just keep ringing when no one was home. Now she can constantly reach him.  

So he should end it. 

“I am writing to you as a fan, but also as a person seeking help with an awkward situation as we are on the doorstep of another football season. I am in my early 40’s with three elementary aged children and very happily married. Sex life is mostly average , below average at times with some periods of being on fire.

My wife will occasionally work at night on the weekends. I love to watch college football on the back deck on Saturday nights and have found that if the kids have friends over to spend the night, I am bothered much less by my kids and can drink and watch the games uninterrupted.

I have used this as an opportunity to be a good friend or neighbor and allow the parents of these kids to go out on the town, have a romantic night, or just do whatever the hell they want, kid free. I figure that I am stuck at home anyway without any chance of getting laid, so why not let someone else enjoy a night out with their spouse?

It dawned on me mid season 2015 that this may have a very creepy appearance. Why does this middle aged man always invite kids to his house, but only when his wife is gone to work? I just want to watch football and hope that I can help someone else get some time alone with their spouse. Tell me , as an expert in awkward situations, am I being a good friend or a creepy middle aged dude?”

You’re being a good friend, but why not just clear up the confusion in advance — you’re also doing this because it’s easier for you to watch football if your kids have friends to play with.

It’s not like you’re just inviting 100 neighborhood kids over and playing tickle monster for six hours straight.

You’re drinking and watching college football on the back deck while your wife is working. And you can drink and watch college football easier if your kids have friends over.

This is kind of a genius move on your part and I don’t think it’s creepy at all. Just be honest about why you’re making your decision.

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.


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