Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday and the Anonymous Mailbag is guaranteed to entertain you. Send your questions to, anonymity guaranteed. 

Next Saturday we head down to the beach for two weeks — don’t worry, I’ll still be writing and doing the shows, just from the beach instead of Nashville — and we’ll be staying in a beachside mansion thanks to my friends at They can hook you up too, all you have to do is go check out their website and tell them Outkick sent you.

Okay, on to the anonymous mailbag. 

“So my boys and I just got back from a bachelor party in New Orleans. We had a fucking great time, one for the books. Nobody died or got arrested so it was a successful bachelor party, or so we thought. I’m sitting in my cube this morning miserable, reviewing the weekend in my head, pounding waters, and hating my life when I receive a text from said bachelor saying “So she’s pissed. I had to tell her something so I told her I got motorboated once and now she’s saying I cheated on her and that she wants to cancel the wedding. So dramatic.”

All involved clearly think this is ridiculous, except of course the bride. This is literally the worst (best?) thing that happened to him all weekend and he didn’t even ask for it. We paid the stripper and told her he was the bachelor. But she’s flipping out and has already started canceling meetings for planning the wedding. So my question is, is this cheating?”

No, this isn’t cheating. 

Not even close to cheating. Especially if you factor in a bachelor party on Bourbon Street in New Orleans. This is literally the best possible result for her. (The worst possible result is herpes.)

In fact, if news about her canceling the wedding over him getting boobs in his face at a bachelor party gets out then everyone, even the grandmas, would think she was being ridiculous. Honestly, if she cancels the wedding over him motorboating some boobs at his New Orleans bachelor party he should consider himself lucky because the rest of his life is going to be miserable.

In fact, if I were him I’d consider a strong power move here and argue that she can’t cancel the wedding because he’s canceling the wedding over her reaction to this story.

Bang, she’d have no idea how to respond then.  

“I was a gorgeous toddler, often confused as a demigod with my bright blue eyes and curly blonde hair. My girlfriend saw a picture of me when I was that age and loved it and asked for a copy. She now has it taped on her night stand. We’re both 22 right now so definitely not looking to start a family. She takes birth control, should I be worried she won’t take her pill so she could use my genes and have her own demigod looking kid?”


Also, this is really weird behavior by your girlfriend.


“My wife and I have a 4 year old and live in CA, where good babysitters are $13/hour(!). My wife is often too tired for sex most nights, so most of our sex is daytime weekend sex while our kid is napping. So my absolute best chance for some nighttime sex is after a date that’s included some romance and alcohol. The problem is that I keep getting cock-blocked by our babysitters. We have three main babysitters, we’ll call them A, B, and C. A is our kid’s favorite. She’s really nice and my wife worries the least while we’re out, which is also a plus. However, she likes our daughter so much that when we get home she tells us 10-15 minutes worth of stories about what they did. As you can imagine, by the time she leaves the mood has been killed and the alcohol has worn off some more. B is our kid’s second favorite. She doesn’t tell us much, but she’s in high school and doesn’t have a car. By the time I drive her home and get back…you guessed it, mood killed and alcohol worn off. C is our daughter’s least favorite of the three, but she doesn’t talk our ear off and has her own car…thus creating my best chance to get laid. But of course she’s the third person my wife calls because she’s my daughter’s least favorite of the three. Like you, I’ll never have a male babysitter watch my daughter, but at least a male would understand the need to scram so that I can get it on with my wife after a date, right? How do I get our female babysitters to understand this? So even though you’re a rich dude with a nanny that doesn’t have to deal with this problem… would you rank the three options and what is your advice to counter the cock-blocking effects of A and B?”

The next time the babysitters are over, after your wife gives the instructions to them — wives inevitably over do it and treat the babysitting instructions like the babysitter has just signed up for a trip to the New World in 1646 — you pull babysitters A and B aside and tell each of them that you’ll give them an extra $20 if they leave within three minutes of you getting back. 

You can even tell babysitter A who likes to give you a detailed rundown of the evening — seriously, is this really necessary? “Then we played, then we watched Caillou, then we took a bath and read books…” it’s not like they performed Shakespeare in French — to write it all in a note for your wife.

Then you get your chance to sleep with your wife.

And, by the way, there isn’t a dad reading this right now who hasn’t been in this situation. Wife’s a little bit drunk, sex is likely, and then 25 minutes later the babysitter is still talking. Night is totally ruined.

(Also, $13 an hour doesn’t seem that bad to me, we pay $14 for all three kids here in Nashville. Furthermore, the only time I need cash these days is for babysitters and strippers. It’s such a damn racket. That’s $14 tax free in cash and most of the time your babysitter just sits and reads a book or watches TV while the kid is sleeping. Plus, my wife always feels bad if we’re going to be late and has to call them? What? For what we’re paying they should be happy to sit there all night.

Also, I love the cocky babysitters who ask for the wifi password. It’s like they just walk up and slap you right in the face. “Yeah, bitch, you’re gonna pay me $14 an hour and I’m going to watch “13 Reasons Why” on your Netflix account for most of the time while you’re gone. Then if you don’t tip me I’m going to talk to your wife for as long as necessary so she doesn’t want to sleep with you anymore.”   

What else are you going to do? The babysitters just own you.)

“My life long friend is getting married in a month. We were best friends all through school and kept in contact in college. We are both about to graduate. I assumed he would contact me about being a best man and at the very least a groomsman. Neither happened. So I found out one of our other friends is the best man. No big deal just trying to hang with my bro before he gets tied down. I ask the best man about the bachelor party and he says they already have it planned out and they didn’t have room to add any more people. Now, being the resentful man that I am, I’m going to try to bang one of their sisters. The groom’s is a 6 but has a wild side to her that I’ve always liked. The best man’s is a 8 but I’d have to pull a rabbit out of my ass to pull that off. Figured I’d hit up the all knowing Clay to help me solve this dilemma.”

Good luck with the sisters, but the bigger issue here is straightforward — your “friends” don’t actually like you very much. 

Seriously, if you thought you were going to be the best man and you didn’t even get invited to the bachelor party that’s a huge sign that you need to find new friends.

Short of writing, “I FUCKING HATE YOU,” in bold letters on the front windshield of your car and signing his name I’m not sure what else he can do.  

I’m sorry.  

“My son was photographed at a school tennis practice wearing a “Make America Great Again” hat. Somehow, this picture was chosen as the team photo and the coaches wife took the picture on her phone to Walgreens to have it downloaded and copied for all the kids on the team. She didn’t notice when she picked up the copies, but someone in the Walgreens photo department edited his hat out of the picture!! It went from red to solid black. Can you imagine if this would have happened to a kid wearing a black lives matter shirt or hat? Al Sharpton would be inciting riots at Walgreens headquarters. What if they had photoshopped a hijab off a girl because they don’t like muslims?

I’m not sure whether to be mad or not. I just can’t stand that someone altered our photo for their political beliefs. The funny part is that he’s not even old enough to vote, his prankster uncle sent it to him.”

I’m willing to bet that the coach or his wife asked them to change the hat and then is just blaming Walgreen’s for the photoshop to avoid an issue with you. That way they can avoid the team photo having a political statement and blame someone else for changing it.

That’s honestly what I would counsel in their position. 

When in doubt just blame the corporation for sucking. It’s virtually flawless strategy. 

The best way to know for sure though? Take the original photo to the same Walgreen’s yourself and see what happens when you ask for copies. If the hat is getting photoshopped out, send the pictures to me and we’ll turn it into a big story. Hell, if you want to do your own experiment, you can have your son photographed in a variety of political hats and see which ones make it through untouched.   

“To make a long story short I’m almost two years out of college & I meet a 20 year old girl on a popular dating app. The girl is a sophomore at an SEC school. I have a full time well paying job. I blow her away on the first date: take her to a nice restaurant, give her flowers (she later tells me nobody had ever done this for her). We hit it off and begin officially dating. We text & talk daily. Her friends totally love me and tell me how awesome & great I really am. Things go well and we begin seeing each other regularly on weekends since I work in a major city about an hour away. I would visit her and grab a hotel for the weekend etc. She is heavily involved in the schools athletics & sorority. She would come visit me on the weekends. During our relationship she tells me how awesome I am & how she has never been treated so well etc.

Fast forward a few months later I take her on an amazing date. About one week later I get a call from her telling me she is breaking up with me. She tells me it has nothing to do with me but her schedule is too busy & it was hard to make time to see me. In the weeks since she instantly looks at everything I post on social media almost instantly. This girl was the total package in my mind…we had so much in common. I can honestly say we never once got mad or argued with each other. We agree to be friendly & she tells me she doesn’t want me to hate her. I come to you seeking your infinite wisdom on the situation. So what’s my play here? Ride this out until after she graduates & make another run at it or move on?”

You’re 24 years old and she’s 20. You play this totally cool. Tell her she’s right to make this move and have fun while she’s at college, that you even felt guilty dating someone as young as her, but that you had such a good time you made an exception. 

Then just leave it at that and play it totally cool. 

You live an hour from her school and you now know all of her sorority sisters. Have you even thought about how awesome this can be for you as they graduate, move to your town, and you run into them out at bars in the city?

Whatever you do, DON’T BE A PUSSY HERE. Don’t chase her at all, don’t even give her a second glance. Just move on and be the cool older guy. Odds are she or one or more of her sorority girls will come chasing you back. 

But only if you play it cool. 

“Your mention of “Fifty Shades of Grey” a couple of weeks ago prompts me to tell you my story. My wife and I have been together for over 30 years. She was, and still is, as we said in the 80’s, a “stone cold fox”. However, for the first 25 years or so she never really cared for sex. She would occasionally do her “wifely duty”, but we would often go for months at a time without sex. She was the love of my life, though, so “Rosy” and I just dealt with it. She always talked about how perverted anyone who watched porn had to be, but I noticed that whenever we watched a mainstream movie that had some steamy sex scenes in it, it would make her horny as hell.

As often as I could, without being too obvious,I would rent those kinds of movies, and it usually worked. Still, some years we had sex only 5 to 10 times. Then, a few years ago “Fifty Shades” came out. It was all the rage, so my wife decided to read it. OMG!! She read the entire series, and for that period of time she was reading it, we had more sex than we had had in several years combined!

Alas, after she was done, the doldrums returned. After a few months, I was wishing there were more books like that so I googled “books like 50 shades” and WHO KNEW THERE WERE THOUSANDS OF THEM? So I picked out a series with good reviews and lied to her that I saw on the Today Show that this book was the next big thing, so she got it and OMG there we went again!

After that she actually asked me to help her find more books and our sex lives went through the roof. That in itself would be great, but wait–there’s more! A year or so ago I was sneaking pornhub (as all guys do) and got an idea. I created an email account, found a “tasteful, romantic” 5 minute video, waited for a night when I knew she was feeling frisky, and sent it to her with a subject of “how to have a happy marriage” or something like that. Well, after bitching for a few minutes about why she would have gotten such a perverted email, and some “come on, let’s just take a quick look” by me, she let me click on the link and OMFG!!!! Needless to say, now she gets an email 2 or 3 times per week. So, here we are in our 50’s, and she constantly reads erotic romance novels and 3 or 4 times every week we watch porn together and then have mind blowing sex! And no, I don’t yet need meds in order to perform, but yes, sometimes things don’t work like they used to. Then, she usually gets me going with an excellent BJ (which never happened prior to “50 Shades”). Sometimes even that doesn’t work, so I just take care of her and we try again another night. I swear it’s all true. So, some advice to your young readers who might be going through the doldrums themselves: Just be patient and creative, and maybe someday your dreams will come true as well.” 

See guys, in twenty years your wife might want to bang you all the time.

It’s worth it!

Send your anonymous mailbag questions to, anonymity guaranteed. 

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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