Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the greatest weekly column on the Internet, the anonymous mailbag. 

Send your anonymous mailbag questions to and I promise to keep you anonymous forever. 

Also, why stay in a crappy hotel or a cheap condo for spring break when you can stay in a mansion on the beach on 30A. Check out where I stay every time I go to the beach at Mention Outkick in the booking notes for 5% off for all of March and April.  

Okay, on to the mailbag:

“I’m a South Carolina grad, and lifetime Gamecock fan- so you understand my athletics futility. I also happens to be an ordained minister. I have a friend that is willing to pay for my flight and hotel room if I go to Phoenix for the final four with him.

Here’s the problem.

I’m scheduled to to officiate a wedding on Saturday. I’ve known the groom and his family for over 25 years, we’re close and he’s a huge basketball fan who would completely understand. His mom and his bride would not understand…

What do I do? Am I a jerk for even considering this?”

You book a refundable flight for Sunday and fly out for the national title game if South Carolina wins against Gonzaga on Saturday. That way you marry the couple — avoiding making the mom and wife angry at you forever and fulfilling your ministerial obligations — but still have the option of attending the game in person if the Gamecocks play for the national title on Monday. 

Plus, it’s the more important game. 


Am I the King Solomon of the Internet or what?

Also, I love the number of ministers who read the anonymous mailbag. It’s fantastic.

“Longtime reader, first-time anonymous mailbagger. The wife of one of my friends dabbled in modeling for a couple years prior to them getting married. Like many aspiring female models, she stripped down and took some nude shots with photographers while building her portfolio, hoping to be noticed and end up in Playboy or some other magazine someday, I’m sure.

A few of those pictures are posted on a photographer’s website and, being a male with a penis, they have been observed while getting myself off on more than one occasion. Two questions for you based on this knowledge… 1. Is pleasuring myself to them wrong? and 2. Do I have an obligation to tell my friend I’m aware these pics exist? (Meaning someone he knows – not just random people on the internet – can see his wife nude on demand.) I only see my friend and his wife once or twice a year on average, if that makes any difference.”

Let’s take it out of your friend’s perspective and pretend that your friend was Keith Urban and his wife was Nicole Kidman. And then ask this question: do you think Keith Urban’s friends, and probably Keith Urban himself, have ever jerked off to Nicole Kidman’s sex scenes in “Eyes Wide Shut?”

Certainly the answer is yes, right?

So I think it’s to be expected that if your wife — or husband — has done publicly available work involving sex that others will seek it out and pleasure themselves while watching it. That’s why those scenes exist. 


Put it this way, if I found out that one of my buddies was marrying a girl who used to do porn what would be the first thing I did? Go to pornhub and look up her porns. Same thing if I found out that one of my buddies was marrying a girl who did Playboy.

I just think that’s totally expected 

The bigger — and more difficult — question here is how did you find the naked photos online? Did you know she was a model and just Google her name and they came up? If you can find the photos simply by Googling her name — which I think is the most likely way to find them — then I think you have to expect that they know they’re up there online.

That’s because I find it hard to imagine in this day and age that very many people haven’t Googled their own names at some point to see what’s publicly out there about them. I think that would be even more true if you were a model.

So I think the question you have to answer is how aware are they that the photos exist online? In other words, how far into creep mode did you have to go to find them online? And if you had to go way deep into creep mode to find them, you go to your wife and say, “Honey, one of our buddies found these pictures online and emailed the link to me. It’s (insert name here)! I knew she modeled, but I had no idea these were still online. Do you think we should tell (insert woman here) that her naked photos are online?”

Then it’s your wife’s decision to decide what to do you and your conscience is clean. 

“My sister-in-law texted me today and asked if I would be Spiderman at this party and said that she has already found me a costume. I am 22 and this isn’t necessarily how I envisioned getting ready for the Final 4 games on Saturday. Of course, she included how much my nephew and his friends would love it and has already told my mom about the idea. Mom says I have no choice but to say yes. What’s the play here? Bite the bullet and shoot fake webs for a couple of hours with 5 year olds or say no and have my sister-in-law hide her hate for me for years?”

You 100% dress up as Spider Man. 

And you Snapchat the shit out of that and one of the girls who follows you over Snap will end up banging you for doing it because it will make her like you more. You think I’m lying, but this will convince her you are A+ dad material in the future.

Also, it will actually be pretty fun. 

I dressed up as Darth Maul at my four year old’s birthday party and terrified every kid there. It was awesome.

And when I was five my cousin dressed up as the Incredible Hulk and came running through the party scaring every kid there. So I think it’s a no brainer.  

“On Saturday night four couples went out to celebrate one guy’s birthday. Well throughout the evening a different guy proceeds to order five rounds of shots without asking people at the table if they want them or the table discussing the shots. Well, the end of the night comes and all the shots are on his bill and you can tell him and his girlfriend are pissed but they pay anyway.

I wake up to a text message from him in the middle of the night saying he is upset that even though one guy ordered all the shots he felt we should all pay.

So is he the dick for continually ordering shots and expecting everyone to pay or are we dicks for not paying?”

You’re dicks for not paying if you took the shots and didn’t offer to split the costs on your bill. 

Now let me explain my thinking. 

It was a birthday celebration and you’re all eating together. In situations like these I’m of the opinion that all four couples should evenly divide the check, not allowing the birthday guy or his girlfriend/wife to pay. So in this situation that would mean you’d split the check three ways. That should include all alcohol ordered at the table, including the shots, beer, wine and mixed drinks. 

I understand that some people don’t like to evenly split checks because they feel like they should only pay for what they order and “If I only got a salad and water why should I pay for…” It’s my experience that the people making this argument tend to be women, who are almost never paying for the meal, or any meal, at all. Remember, #hotgirlprivilege is real. For instance, I’m not sure that my wife has ever paid for any meal that we’ve ever had together. I mean, ever. From the time we started dating when we were in law school together at 23 years old to now.  

If you don’t want to split the check evenly then you should split it by couples and include all alcohol being evenly split. (This would be different if some people don’t drink at all, but here everyone drank.) 

If this guy ordered five shots for the table that’s 20 drinks. Let’s assume they cost, on average, $10 each. (It could be higher or lower, clearly, but let’s make the math easy), That means he spent $200 on alcohol for the table by himself. Given that everyone consumed the shots, I think you guys should have offered to help him out. Moreover, if he was upset enough about it to text you later, it probably means that he isn’t independently wealthy and so wasn’t intending to subsidize alcohol for everyone. (If the guy was independently wealthy and he’s ordering the shots then things change. Then it would be reasonable for you to assume that he was treating everyone because he’s rich and could afford to do so.)

What should have happened, honestly, is after this guy ordered the first round of shots then someone else should have stepped up and ordered a second round of shots and so on until everyone had each ordered a round of shots for the table.   

But you didn’t do that. You just keep letting this guy order shots and then didn’t pay for them.  

So this guy may have felt like he was making the party better by being order shots guy! And, honestly, what dinner party isn’t better with everyone drunk? He was probably right. 

Make it up to him by telling him you’ll buy the shots for the table at his birthday. Then ensure you can split that cost with the other guy who skipped out on the birthday party without paying for the shots.  

“This weekend, one of my best friends revealed he pees sitting down all the time. He will wait at a bar for a toilet so he can sit to pee. He literally never pees standing up. How weird is this action and should I be able to make fun of him forever?”

It’s really weird to pee sitting down in a public bar. That’s genuinely psychotic behavior. 

I don’t even like walking into most public bathrooms, much less sitting down on the toilet. 

Having said that, I don’t think it’s that weird at all to sit down to pee at home. For instance, if I get out of bed at night and have to pee, I always sit down because I don’t trust my aim in the middle of the night. 

You should make fun of him forever about this. And you should also tell everyone you know about it. Public shaming is healthy.  

“Clay, I wanted your expert opinion on this, as you are a guy who left your field to follow your passion. My passion has always been for sports betting. I got into it as a teenager and was always interested in more than just “can I win?” I was a fan of the whole process; the line setting, sharp betting vs square betting, how millions of people are willing to partake even though the numbers say they will lose money long-term. My dream in life was to move to Vegas and get a job at a sports book and eventually work my way up to a high-level position. I just love the industry.

Well, life happened, I got a job in insurance and met my wife, and moving to Vegas, where there are legal sportsbooks, never happened. Now, I am 30, about ready to have kids with my amazing wife, and making decent but not insane money. It also is looking like in the not too distant future, sports betting is going to be widely legal, and books are going to start popping up all over, including in my city that already has some great casinos and will certainly add a book when the law says they can.

My question; am I too old and is it too late in my life for me to get into that field, if it means I will likely have to take a job as a ticket writer making very little money to get my foot in the door. Obviously, the long term plan would be to work my ass off and move up, but if I want to just get into the game, I would likely have to take a not glamorous position making little money to start. Is it weird to do something like that at age 30 (or 31 or 32 when the law actually changes) and willingly take steps backwards financially at a time in my life when we are looking to have kids, buy a house, etc even if would be a way to enter the business I have always wanted to be involved with?”

I don’t ever think it’s a bad idea to chase down a dream, but I do think you have to be somewhat realistic once you get to be 30 or older and are talking about having kids.

So my first series of questions are these, what does your wife do? How reliable is her job and does she make enough to support your lifestyle as a couple and allow you to pursue your dream? Have you talked to your wife about what she foresees her life being like once you have kids? Is she thinking, as many women are, that one day she’d like to stay home with your kids while you work? Have you ever told your wife, and this is important, your dream is to work inside the sports gambling industry? (If not, this conversation is probably not going to go very well. I doubt there is a woman alive who has always dreamed of her husband working in a sports book.) This is a legitimate conversation that you need to sit down and have with your wife before you decide whether to try and chase down any job different than the one you have right now.

Second, you need to figure out what kind of money you can make doing this job. Do you really want to sit at a ticket window and print tickets at 32 years old? Are you okay making $30k a year? Are you romanticizing the job? You should go to Vegas and sit and watch what the guys who work in a sports book actually do. 

If I were advising you on a way to get involved in the gambling industry, it would be to focus on where the real money is. Try and get a job involved in the business side of sports gambling as opposed to the labor side. Be strategic now in considering those angles. You said that there are casinos in your hometown now. Have you considered trying to get a job there? After all, that’s probably where the sports book would be some day. If you already work at the casino don’t you think you’d have a decent chance of moving over to the sports book if sports gambling becomes legal one day. 

“My buddies and I get down to the beach for spring break on a Saturday evening but we were not able to get in our room until two the next day, which was Sunday. So, we knew going into this trip that Saturday night we were going to have to bum it. Anyway, Saturday night we start partying and I ask one of my sorority girl friends if I can stay on her couch knowing that she would say yes… and she did. The night goes on and we found ourselves back at Sorority X house. Well, apparently they have this stupid rule of “no guys allowed to stay here” which I just cannot comprehend at this point.

Do you think the no boys allowed to stay rule is bullshit? I do… it’s fucking spring break. There’s no way someone didn’t break that rule all week. Anyway, they start trying to kick all the guys out. Now, I am not 100% sure of what I said but I made it clear that I was going to sleep on this couch no matter what because I had nowhere to go and NOBODY was sleeping on this couch. So what’s the big deal right? There were 12 girls in the house. 10 were upstairs and 2 were downstairs near my couch on another bed. So, why the hell can I not sleep on this damn couch that nobody is sleeping on? Sooner or later I end up passing out.

I wake up at 8:45am (on the couch, still plastered) to one of the girls yelling at me, telling me to get the fuck out. I mean she was LIVID. I was not doing anything. I was sleeping for goodness sakes, not bothering anybody. We bickered back and forth and I finally end up leaving a few minutes later. Later that night I run into her at a party. First thing she does is grab the beer out of my hand, walk to the front door, and Hail Mary’s that shit into the street.

I was pissed.

A bunch of arguing ensued with some of the other girls in the sorority but obviously no physical altercation. Clay, I would not hesitate to help any of the girls out if they ever needed it. Especially my ex-girlfriends littles. If they were standing in the pouring down rain and had no place to stay and knocked on my door I would without a doubt allow them to stay regardless of the situation. What all did I do wrong here? Am I wrong for staying on that damn couch? Are they right to hate me? Are the bad looks they have been giving me on campus justified? Even more, how should I have reacted to her throwing my beer like a baseball out the front door? I’d appreciate your insight.”

The girls were upset with you because you refused to accede to their wishes and you’re too big to force out of their place. Whether or not their prohibition on boys in the residence made sense — it doesn’t — you expressly refused to leave when they asked you to and didn’t leave them with any real options when you stayed there on their couch. The other guys you mention agreed to leave, why didn’t you?

What if there are significant consequences — to them anyway — inside the sorority if they get spot checked on a surprise spring break visit and you’re there sleeping on the couch? What could they do when you refused to leave? Call the police on you? That’s an excessive response that they didn’t want to undertake. The only thing they could do is have the girls you are the best friends with in the house ask you to leave. The girls who know you best in the sorority were upset because you didn’t listen to their requests for you to leave and their friends in the sorority held them accountable for your not listening.

Yes, the rule was dumb and I understand why you were upset given that the couch was open, but you went on spring break a day early without a place to sleep and then refused to listen to their wishes when they told you you couldn’t stay there. They didn’t create a bad situation for you, you did.   

Tossing your beer outside wasn’t ideal behavior, but it pales in comparison to what you did to them. You’re in the wrong here. Your friends in the sorority have a right to be upset with you. Quit being a dick and apologize so you can start sleeping with them again.  

“Just read last week’s anonymous mailbag, and felt compelled to email because I’ve been propositioned by couples two times while in college. I’m a pretty average looking guy. Once I was at a bar at Mizzou (while a student) and a late 20’s or early 30’s attractive women was near me at the bar and I struck up a conversation. She joined me at my table, we chatted for a bit and she asked if I wanted to head back to her place with her and her husband. I was freaked out by the husband part and said no. Her husband was hanging out near us (I guess waiting for her to pickup a college guy) then came up and introduced himself. He left me his card saying if I changed my mind to give them a call, his card said he was a prison guard captain so I’m definitely glad I said no.

The second time was at a random house party at Mizzou. I’m hammered and an attractive older women (probably early 30’s) sat down next to me in a room in the basement where everyone was allowed to smoke. She started rubbing her hand up and down my leg and grabbed my hand to do the same to her. We’re chatting and touching each other when her husband sat down opposite side of her. He started asking questions like “isn’t she hot?” basically egging us on. She then asked if I wanted to join them in an upstairs bedroom. I was young and naive and was weirded out by what he would be doing while we were up there and after a minute of discussing I said no. Looking back, I would have done it if I’d made sure he sat in chair and didn’t join us.

I’ve never been a swinger and I’m not into couples, so I’ve always wondered why these two couples thought I would be down to joining them. Both times happened within about 6 months of each other.”

I don’t blame you for your decision I would totally expect to wake up in a bathtub without a kidney in either of these situations. 

Send your anonymous mailbag questions to, anonymity fully assured.  

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.