Anonymous Mailbag

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Charlotte McKinney, Kliff Kingsbury

It’s time for the most popular weekly column on the Internet — the anonymous mailbag!

As always you can email me at and I guarantee your anonymity. 

Okay, on to the mailbag.

“My wife and I started dating as college freshmen at age 18, and we’re now in our 30s.  We were recently cleaning out some of her stuff from her parent’s house from before we got married. I was going through some photos and came across a picture of of her in a bikini. I made a crack about saving that one for my personal use later. She didn’t think it was funny, and said that the photo was from her senior trip in high school and I would be a pervert to want to keep it.  

I could see her getting upset if she had changed a lot since the photo, in which case my reaction could come off as a backhanded commentary on her appearance now. But my wife is hot. She cannot be more than 10-15 pounds heavier than she was in the photo, and she definitely has a nicer rack after having kids.  

What is your ruling on this? Am I a pervert for commenting on the picture (given that we were dating and having sex within months of when it was taken)?”

This is such a great question: Is it creepy to jerk off to your wife’s senior year in high school bikini pictures when you are in your thirties (or older)?

The answer’s no, it isn’t creepy for two reasons: 1. You are still so attracted to your wife that you’re jerking off to her and 2. She still looks somewhat like she looked like in the photo.

If she had put on like a hundred pounds and you were jerking off to her in a high school bikini this would clearly be passive aggressive jerk off behavior, but that’s not the case here. Furthermore, it’s not like you met her at the age of 45 and never knew her back when she was a senior in high school. In which case it might be considered creepy. But you actually knew her in close proximity to the age so there’s no time issue at play.

Here’s an easy way to answer this question, would it be creepy if you guys had made a sex tape when you were 18 and you still occasionally jerked off to that sex tape 15 or 20 years later? Of course not.

Are you telling me that Tommy Lee doesn’t occasionally watch that old sex tape he made with Pamela Anderson and jerk off to it? Or that Ray J never watches his sex tape with Kim Kardashian and jerks off to it? Of course those guys do.

It’s the same thing here except you’re actually still with her. So you’re even more golden than Tommy Lee and Ray J. (Although, to be fair, it’s unlikely your penis is as big as theirs.)  

Women may not understand it, but if your husband or boyfriend wants to jerk off to your picture, screw holding the door open, this is like the nicest thing he can possibly do for you. It’s the ultimate compliment.

Do you know how much porn there is out there that’s easily accessible and features nubile young nymphos? And with all that tits and ass out there, he’s picking you to jerk off to!

Your wife should have been so honored by your bikini photo request that you don’t even need to get her a Valentine’s Day present this year.

If she is still arguing you’re a pervert after reading this response, suggest a compromise, she takes current photos in a bikini — and maybe less — for you.  

“My girlfriend’s a couple years younger than me and still in college while I have graduated. She’s amazing, drop dead gorgeous and my parents seem to really like her. However, they also hint that they’re afraid of the age gap we have and think she’ll end up ending it because she wants to be free in college. I’ve assured them that we’ve talked about that plenty of times and I don’t think that will happen but if it does I would totally understand as I had a lot of fun in college.

The problem I’m faced with now is Halloween. As you know hot girls like to dress up in rather skimpy costumes, so my girlfriend wants to dress up as a “sexy something.” I’ve told her I’m uncomfortable with it for what I feel are obvious reasons but didn’t tell her she couldn’t as I totally trust her and don’t think she would ever cheat on me. She says everyone does it so it’s fun to do because she won’t get judged for dressing slutty but I totally disagree. Now I didn’t grow up in a religious household and my parents are extremely relaxed about a lot of things but I know pictures will get posted to social media of her in her costume and they will see it which will only lead to their worries about her. I’m afraid my parents will get the wrong idea about her when they see her costume. So what’s my best option? I hate to talk to her about it because I don’t want her to think my parents think she’s a slut (they don’t) and don’t like her (they do) however I’m afraid my parents will think worse of her if I try to talk to them about it or they see it.”

First, you need to stop being such a huge pussy. I hope when you read this email in the anonymous mailbag you think, “God, I sound like a huge pussy when I see this all written out.”

Because you really do.  

And what’s our number one rule on Outkick? Which you are flagrantly violating?

Don’t be a pussy, #dbap. We now have #dbap shirts by the way, and they are selling out fast, so all of you should probably go buy one.

Second, your girlfriend should be able to wear whatever she wants for Halloween and you shouldn’t be involved in this decision in any way. Further, what she wears for Halloween isn’t going to increase or decrease her odds of cheating on you. Do you think the other guys at school don’t already know she’s hot? They’re not going to be like, “OH MY GOD. I totally didn’t want to bang Kayleigh and then she dressed as a slutty nurse and now I want to bang her so bad!” Everyone always wants to bang the hot girls in college no matter what they’re wearing. You know this. Also, God bless her if she’s hot and wears a hot ass Halloween costume. That’s why the terrorists hate us, because our girls are so smoking hot.

Like this hot girl from LSU, who got kicked out of the LSU student section for being too drunk and disorderly. (Sidenote, that’s possible?!) I love this girl. The terrorists are watching this and they’re so mad because their chicks aren’t getting wasted at college football games. They hate us ’cause they ain’t us. (And because their girls are ugly.) 

Third, your parents need to get out of your relationship. You’re a recent college graduate and your girlfriend’s a current college student. Odds are you’re going to break up at some point. So why do your parents need to be involved in your relationship to the extent that they care what your girlfriend wears to Halloween? You want to talk about creepy? That’s creepy.

I have three sons. When they’re off to college if they have girlfriends and those girlfriends dress up in smoking hot Halloween costumes, I’m just going to give my sons a fist bump and say well done. In fact, I’ll be disappointed if they’re dating girls that aren’t dressing up in smoking hot Halloween costumes. 

Because then they will have failed at college.

Tell your girlfriend to call you when she gets home from Halloween partying and FaceTime you while she takes off her slutty costume.

Then everybody wins.

See, here I go again solving America’s problems.  

“It’s way too early in my life to be dealing with this but I’ve recently been told I have high blood pressure. Between bad genetics and being a Vols fan this year, it was bound to happen sooner or later. So I’m visiting with my doctor about medicine and plan of action recently and they start telling me side effects of the medicine they want to prescribe to me. The one they lead off with is “You might experience erectile dysfunction…”

I don’t even know what to say but the best part is what is said next. To assure me, the doctor says, “But don’t worry, if you do get ED, we’ve got something for that we can give you.” How did I become a 60 year old man in an instant? I’m married with a young kid so getting sex is already hard to come by, but now I might not perform when the rare opportunity comes up? Why can’t I just have Clay Travis genetics and hair? Now I’m face with this harsh reality and don’t know how to face it. Too early for a mid-life crisis?”

How bad is your blood pressure that you need to take medicine already? You can’t treat it with other healthy life decisions?

I’m 37 and I don’t even know what my blood pressure is right now. Are there that many young guys with young kids on blood pressure medications? My first bit of advice, and this is for life in general not just your situation, is I don’t want to take any medicines or pills or anything unless they’re absolutely, positively necessary. And sometimes they are, but lots of times I believe that doctors — and the medical industry in general — are incentivized to overmedicate us because it makes them money.

I think we could cut at least half the prescriptions in America today, probably like 75% to be honest, and see no material change in the nation’s health.  

If you’re a young person than rather than starting to mix drug cocktails to make sure my dick works, I’d ask if there are any natural decisions I could make to try and lower my blood pressure without medication. Then I’d go back in a few months and see if those natural decisions have worked.

If they haven’t, you can give up your dick. 

“I live in the Dallas-Fort Worth area and have a decent commute, 40 minutes at best, 50 minutes on average, worst case I’ve had so far was 3 hours because of an ice storm last year. Typically it’s not an issue but on that three hour trek last year I was about to crap my slacks and seriously considering hopping out of my car and popping a squat. What is anyone going to do about it? Not like the police can show up and arrest me in standstill gridlock for as far as the eye can see. In my mind, I think one person breaking down the barriers of public decency would ignite a revolution and dozens more would join me in relieving themselves right there on the highway.

So what’s your play in a situation like this? For a #1 I’m definitely sacrificing my coffee cup or any water bottles in the car. But for a deuce things get a lot more complicated if you’re interested in maintaining social order. As we head into crappy weather season I need your wisdom in creating a plan for when shit goes down.”

I think you do your best to run into the trees on the side of the road. But what if you’re on a crowded interstate and there are no trees and cars haven’t moved for hours? Man, that’s a really tough situation. 

My first thought is it would be hard to poop in that situation because lots of people would be looking at you. But I just came through an awful week of poop and puke sickness in the house and if I’d had that going on I have zero doubt I could have pooped on the 50 yard line at Neyland Stadium while the band played and they put me on the Jumbotron.

That’s how impossible it was to control my craps. 

I haven’t ever had this traffic issue arise, but now I’m wondering if I should carry toilet paper in my car just in case this happens for me or any of my boys.

I think the best play in this situation would be that you have to pull your car off to the side of the road — the one not closest to oncoming traffic — and then you open the front and back doors and squat down between the car doors. With the doors open you’ve created a car stall of sorts. Depending on your car’s size and your squatting capabilities, it might even be nearly impossible for people to see you. Then you crap right there on the side of the road. 

I’d use my boxers/underwear to wipe my ass and then just abandon them on the side of the road. Sure, it’s littering, but you might be in you car for hours, you can’t handle that stench.   

I think that’s the best play by far. 

“As a 31 year old woman with kids and a husband myself I felt compelled to say what I believe is the one of the biggest causes of women not being interested in married sex.

I’d take 90-1 odds this woman is not cumming at all during sex.

My guess is she has been faking orgasms their entire marriage. You have no idea how common this is. If she’s not getting off, pretty soon the sex just feels like a job and one more thing on the to do list. She needs to find out what makes her cum, and then teach her husband what works. This could save marriages if women would just freaking do this. My husband and I have sex like 4-5 times a week barring work trips, sick kids etc. I work as a RN and have 3 kids 5, 3, and 9 months old! So ladies don’t give me that “I’m tired” bullshit! #dbap!!!!!!

Are we unicorns? Does anyone else have healthy sex lives? From what I’ve read in the mailbag and what my friends confess, we are completely the exception. There are other theories of course, she could be depressed, low libido due to hormones or medication, etc. But I feel like my first theory holds true most often. You don’t suddenly become unattracted to your husband immediately after marriage. If he’s not cheating on her yet, he will be and justifiably so. Wives-screw your husbands brains out! Men- learn how to make your wives cum!! which usually involves oral or clitoral stimulation not straight sex! This saves all your readerships marriages. You’re welcome!”

I gotta say, women’s emails to the anonymous mailbag are, on average, so much better than the men’s emails. 

We’re going to have an all women’s anonymous mailbag here soon.

And, by the way, if you have friends and family that aren’t reading the anonymous mailbag, how is that even possible? The anonymous mailbag keeps growing like gangbusters, but you need to be sharing this weekly column with everyone you know.

Because I think it’s truly impossible for someone under the age of 45 not to enjoy the anonymous mailbag.  

“Hey Clay, guy in my mid 20s here. So, I’m living in a big city, that has multiple professional sports teams.

Correlating that to girls. So, I’m out, meet this very attractive girl, successful, on the right path and everything. We become friends on IG, and doing what all guys do, I’m scrolling through her past couple of pictures, seeing how many likes she gets, who is liking the pics, etc.

And if I won’t be damned, I see she has a blue checkmark guy liking her pics that plays professional soccer and has oodles of followers.

Now, I’m no slouch, used to play baseball in college and stuff, but I for damn sure aint a blue checkmark.

How should I combat this? Should I wave the white flag? Is she out of my league?”

Is it easier for athletes with blue checkmarked accounts to bang chicks? Of course. But she knows that. So he may have banged her, but that doesn’t mean you can’t too.

After all, he’s probably chasing — and banging — 25 hot girls all at once.

The advantage you have over him is focus.  

At some point she’s going to have to decide, do I want to be one of many girls or one guy’s top pick? Just about every girl is going to prefer being one guy’s top pick. (This is assuming the guys the girls can get are decent and also assuming that the guy isn’t hugely famous. Otherwise, for instance, is it better to be Johnny Depp or Derek Jeter’s sidechick than the average guy’s actual girlfriend? Of course it is.)

Plus, what’s the worst case scenario here? This chick would rather bang a pro soccer player than you. Let’s be honest, you’ve probably gotten beaten out by worse dudes before. If anything, getting shot down for a pro soccer player shouldn’t hurt your ego. It’s getting shot down for a cell phone kiosk salesman or Enterprise rent-a-car clerk that should be a blow to the ego. 

So I don’t see any problem for you here.  

“I’ve been talking to this girl casually for about a year now, aside from her leaving the biggest hickey known to man on my neck, we have never done more than made out before because “she’s not that type of girl.”

After some time, I come to find out she is a virgin. I don’t know your thoughts on this, but a wise man once told me “never be her first, and never be her last.”

It quickly becomes clear that I am not going to get laid unless she’s my girlfriend. I am a senior in college and the last thing I’m looking for is a girlfriend, but I don’t want this to be a complete waste of time. The girl is cool and all, but not that greatest looking girl I have ever been with. My friends think I can do better.

So last week on Thursday, I’m pretty intoxicated and ask her to be my girlfriend. I know that she likes me and know that’s what she wants, but she replies with, “Ask me when you are sober.”

I completely disregard the comment and proceed to keep calling her my girlfriend, in hopes I’m finally going to do the dirty. After a drunken walk home we finally get to my bedroom. Typical pre-bone stuff goes on and I ask if we can bang. She tells me she’s in as long as I have a condom. So this puts me in find a condom mode, I am tearing apart my room checking every drawer and every corner of the night stand but come up empty. Never have I been so disappointed in myself in my life.

So the next morning rolls around and I’m still drunk and I reassure her that I want her to be my girlfriend. As the day rolls on, I sober up and am hit with a wave of guilt. So in the end, I wind up with a girlfriend that I really don’t want, and said girl is still a virgin. I need advice. Thanks.”

Break up with her now.

This girl is much more certain of what she wants than you are. (Aside from sex. But you’re a guy in college. All guys are chasing sex. So that doesn’t really count as knowing what you want.)

You’re just going to disappoint her — potentially after she saved her virginity for you, thinking you like her as much as she likes you — and she doesn’t deserve that.

As is, two things happen if you sleep together, both bad: 1. You sleep with her and treat her like a dick because you don’t really like her that much, meaning you have an awful relationship that endures longer than you want it to just because you had to enter into a relationship with her to get her to sleep with you. 2. You sleep with her and immediately break up with her and she’s crushed.

The only way I see this working out is if she’s tired of being a virgin — that is, her prolonged virginity just happened kind of by accident, not by design — and she’s just decided to bang you because she doesn’t really like you that much and isn’t worried about getting emotionally attached, but just wants to lose her virginity so she’s not graduating college a virgin.

But that doesn’t sound like this situation at all.

So break up with her by saying that upon reflection you’re not willing to be as serious of a boyfriend as she deserves.

It’s the truth and it’s the right decision.

The anonymous mailbag runs every Tuesday on Outkick. Send your anonymous mailbag questions to, anonymity assured.  

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.