Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, send your anonymous mailbag questions to Bit of news before the mailbag, we are redesigning the Outkick site and as part of that site redesign Outkick is taking over all ad sales for all our products. That’s Periscope, Facebook Live and website. If you want your brand to be exposed to our audience of millions email and I’ll put you in touch with our ad sales team.

Speaking of which, why stay in a hotel room or a bad condo when you can stay in a mansion on the beach like I do? I’ll be on 30A for two weeks from May 20th-June 4th and I’ll be staying in a house from the guys at 30A cottages. Go check out the beachside mansions they have for rent here.

Gambling picks for tonight: I’m on Wizards +5 & Jazz +13.5

Okay, on to the mailbag. 

“I come to you seeking closure for an ethical dilemma that has lingered on my conscience for the past couple years. I consider myself a pretty loyal friend, but this is the most guilty I’ve ever felt regarding a friendship.

My best friend, whom I’ve known since we were kids — we are in college now –, recently broke up with his longtime smoke show of a girlfriend. I mean, this girl is a 12 out of 10 with perfectly sculpted tits and ass. I have also known this girl for a long time and consider her one of my best girlfriends.

So my best friend is notorious for using the same password for all of his social media accounts. One day, back in high school another friend and I half-jokingly decided to try this password on his Snapsave account. (If you aren’t familiar with Snapsave, it’s an app that allows you to save and upload pictures from Snapchat). We were out mining for gold. Think about it, as a horny high school guy there would be nothing better than a secret porn stash of an otherwise untouchable girl. Fortunately, dreams do come true and the password works. We’re in. The only 2 pictures in the gallery were full-frontal nudes of my friend’s girlfriend. Her tits were so perfect it almost looked like someone had photoshopped her face onto a porn star. In complete shock and disbelief, I quickly screenshotted the pictures and logged out of the account. I also admit that I may have gone home right after and jacked off to the pictures. But, in my post-ejaculation shame that every man feels, I decided to delete the photos from my phone. (I know, I am #ap)

This all happened about 3 years ago and my friend who saw the pictures and I have never spoken a word to anyone about the incident until now. Our friend is the type who holds long grudges, especially over something like his ex-girlfriend, which leaves me in fear that telling even our close friend group would expose my betrayal.

In the past, I have contemplated but restrained from submitting this, since my best friend is also an avid Outkick reader. But now, well, #DBAP.

So my question to you is: What would you have done in this situation? Should I feel guilty about this? Was it wrong in the first place to try to see his hot girlfriends nudes? Would it be funny to bring up to him once he’s gotten over the relationship?

As the supreme authority on all things boobs and the most inclusive man (or woman now, I forget) on the Internet, I humbly seek your advice.”

Such a perfect anonymous mailbag story. 

This is very, very funny. 

Okay, let’s break this down. 

First, you were wrong to break into your friend’s account hoping that his hot girlfriend would be naked there. Once you discovered that his hot girlfriend was naked there, you were wrong to screenshot these pictures and then jerk off to them. (Did the other guy also delete his pictures or is he still jerking off to them years later without the same jerk off remorse as you?) Credit where credit is due, it was the right decision to delete her pictures forever, but I understand the lasting regret and jerk off remorse the one right decision you made amidst your string of bad ones has left you. There is nothing harder than giving up the possibility of ever seeing a good looking woman naked again. 

Having said that you betrayed the confidence of your best friend and his girlfriend with the perfect boobs, who happens to be your good girlfriend too. And odds are both of them would probably be upset with you if you confessed your high school transgressions.

What’s working in your favor is this happened in high school. And now you can spin zone this that you are older and more mature and in college you wouldn’t be interested in things like seeing your friend’s hot ass girlfriend with the perfect boobs naked. (This is totally not true, by the way, but the girlfriend might buy it if you told her this. Your guy friend will know you are full of shit if you try to make this argument.) 

So at this point I would suggest never saying anything to either.

But if you do decide to ever say anything, I think this is an amazing drunk confession at the ten year high school reunion story. By your ten year reunion high school reunion the bad feelings over your failed relationship will be over and you will be 12 or so years removed from being 16 and Snapchat snooping.

The only other suggestion I can offer here to fix this situation would be for you to share naked photos of your girlfriend or ex-girlfriend with your buddy in a fair and equitable sharing girlfriend for masturbation photo exchange. This could theoretically alleviate your guilt and make you both whole again. The problem, of course, is this isn’t fair to your current girlfriend or ex-girlfriend since she didn’t consent to being seen nude by anyone else. This then creates another ethical dilemma in the naked photo triangle here. You could solve this by having your friend send an unsolicited penis pic to your girlfriend or ex-girlfriend, but this creates more problems. (Side note, it’s also hysterical. What if every time you saw someone naked who wasn’t aware you were seeing them naked you were required to send them an unsolicited nude photo?)

Which is why I would counsel silence.

Also, for all the girls with #hotgirlprivilege out there reading this right now, the hotter you are the more likely your naked photos are to eventually be shared with someone other than the intended reciepient. Y’all may not care because every girl between 18 and 30 is already naked somewhere out there on the Internet cloud and nudity — especially if you’re hot — doesn’t have the same stigma it did in the past, but just a word of advice, if you send naked photos to a guy you aren’t married to you should assume that he’s not the only one who will ever see them.   

“A weird situation has developed here recently with a girl. On Friday afternoon, I get a text from a girl, no clue who she was before this, asking if this was me. So, I say yes and she goes on to say that my grandfather just all of a sudden randomly gave her my number. I start to panic then wondering what’s happening because whose grandfather just randomly gives a college girl their grandsons number? Second panic button was pressed when the girls name is very odd and something I’ve never seen for a girl. So I interrogate her about the situation and she plays it off like it’s normal. I look her up on Facebook and she has a boyfriend, but she’s totally being flirtatious. She’s also a solid 7-8. What’s the move, Clay?”

Thank Grandpa for being an awesome wingman and try and meet up with her in person unless her boyfriend is a Navy Seal or seems likely to kill you for texting his girlfriend. 

My rationale on this is simple: if she has a boyfriend she’s sure not acting like a girl happy to have a boyfriend. She definitely looked you up online before she texted you. (Or your grandfather pulled out a wallet photo.) So she’s game to meet up and explore her options. 

Plus, if you don’t try and bang this girl your grandpa can call you a pussy. And among many of your goals in life one of them should definitely be, “Don’t do anything that will let my grandfather call me a pussy for doing.”

“I’m a young CXO who got caught up with an even younger smokeshow who works for me (I’m talking a legit 9. Not just because I’m surrounded by rubbish for eye candy all day and she’s under 25 and not fat, but an actual chick I would consider hot if I was still in college). It started with light flirting and progressed to more aggressive flirting and eventually we discussed having an affair. By the grace of Allah, we decided that wrecking our careers and my family (I’m married with kids) wasn’t worth having a torrid office romance and a ton of hot sex (she’s so hot it was a much harder call than it should’ve been).

Now working together is incredibly awkward. Every interaction is me thinking about banging her and knowing she’s thinking about banging me while discussing TPS reports. The sexual tension is palpable and there’s nothing I can do about it since trying to talk it out would make it even more weird. My productivity has tanked and I’m to the point where I don’t want to come to work anymore. I imagine she feels the same.”  

See if you can get her transferred to a similar job in the company without you as her superior.

But be careful and don’t put anything in writing about the true reason because you don’t want this to turn into a mess for you or the company. Because if, for instance, you write her an email about how sexually attracted you are to her and pour out your feelings, then what happens if this eventually comes out in a sexual harassment lawsuit she files? Or corporate discovery in another lawsuit? (Y’all may think I’m crazy, but what people write in emails would astound you.)

If this email ever went public, do you think your wife is going to be impressed that you were so sexually attracted to a subordinate that you requested her to be transferred away from you to avoid having sex with her? Especially if those emails go public in a lawsuit. I’m guessing the, “See, honey, I didn’t cheat on you even though I desperately wanted to cheat on you,” line doesn’t play that well.

You’ve already had a frank discussion with your subordinate about having an affair and rejected the option. So if you can get her transferred that’s the play. Just tell her that in another time and place you’d want to date her, but you can’t do that now and that you think it’s better for both of your job performances if you aren’t around each other in the workplace. 

“Got invited to go on a float trip with some bros a few hours from home. Been looking forward to it, can’t beat a good time with the boys. My GF has a wedding invite for a Sunday in May, and she wants me to attend with her as a guest. I tell her okay that’s fine. Well the rainy weather causes the float trip to be cancelled and they want to reschedule. What day are they rescheduling you ask? Of course they choose the Sunday of the wedding in May. I tell her I still want to go on the float trip, and she loses it. Says I’m a liar, can’t keep my word, that I’m selfish, the whole 9 yards. I tell her it’s not the end of the world if she attend’s HER friend’s wedding without me, and that I’m not gonna cancel a whole weekend just for an hour long wedding of someone I don’t even know. What’s my play here? Should I go on the trip or stay and go to the wedding?”

Making men go to weddings as guests for people we don’t know is one of the shittiest things girlfriends do to their partners. Why should you have to go to a stranger’s wedding? I’ll tell you, because your girlfriend is desperately insecure because her friend is getting married and she wants to prove that one day she’s going to get married too and to prove that fact she has you there with her.

The boyfriend at friend’s wedding is like a huge flashing light to prove that she’s not a loser. 

That’s because women worry about whether they are going to get married or not. Whereas I don’t think there’s a single guy who ever worries about this. It’s not hard to get married if you’re a guy. Hell, murderers like Steven Avery even get married in prison.  

The only thing worse than being dragged to a wedding is the recent rise of couples showers. Just because showers suck don’t think that including men is going to make them better.  

There’s nothing comparable to weddings and couple showers that men make women attend with them. In fact, what’s the shittiest obligation that men have? Maybe helping friends move? What if we started making our girlfriends show up and carry stuff all day as revenge for weddings and showers? In fact, I’m going to suggest you start this today. 

If your wife or girlfriend says she doesn’t want to do it, just file it away for a get out of jail free card at a future wedding or couples shower. 

(By the way, once you’re married and have kids then this all changes and actually going to weddings will become an awesome social night out for you. There’s alcohol, music, and other people there around your own age to hang out with. If you’re lucky you’ve got a babysitter for the night and your wife will get drunk and have hotel sex with you. And you’ll get to wake up without a kid crying. On any nights that I get to sleep in — which are rare since I get up at four in the morning for the radio show — I have not woken up without a kid crying in my house for like a decade now.) 

“What is protocol for letting one of your boys know his girlfriend outkicked her coverage? Multiple attractive (because everyone trusts a hot girl’s opinion #hotgirlprivilege), mutual girl friends of ours have stated our friend could do much better. She’s not just unattractive, she’s boring. I think he settled for a rebound, but it’s been a while to still be on the rebound.

What would a wise, gay Muslim such as yourself do?”

Don’t sugar coat it — or “sugar code” it as LeBron says — tell him he can do a lot better than the girl he’s with. You can’t hint at this because that’s too awkward to pull off, you’ve got to just let him know.  

But be careful here because it’s possible that she’s one of those girls or guys who wants to isolate a partner from his prior life. Then you’re making that division easier. Because you don’t want to give your buddy a situation where he feels like he has to pick between his girlfriend and his friends.

Because at least in the short term pussy almost always wins.  

“I like to golf, haven’t done much lately after moving, and I come to find out a new(er) buddy of mine is an avid golfer. So I’ve been trying to set up some tee times. Problem is, he keeps trying to insert his wife into the mix, making statements like, “she’s actually pretty good”.

Now, he’s only been married 8 months and his wife is cool so I can understand the want (need?) to include her, but I have never suggested my wife joining us on the course, and I always make a point to suggest two other guys to fill out the foursome. All I want is a few hours on the course with my buddies to drink beer, hit terrible shots, and get out of the house. Is this just the newlywed thing where you think you need to include your significant other in every activity and it will go away, or do I need to explain to him that when I ask him to golf it is strictly assumed that wives are not included? If so, what’s the approach?”

Just be direct with him.

There’s nothing wrong with men wanting to spend time with men or women wanting to spend time with women. If this guy wants to golf with his wife, the two of them can do it without you.  

If you need a joke tell him this say, “The only guy I’m willing to play golf with that hits from the ladies tee is you.” 

“I have coached middle school basketball for the past 15 years, and the other coaches and I have always utilized the hot mom theory when it comes to picking players, but with a caveat. While we will typically keep 12-14 players on the team, the first 10 are always the best players out there. When it gets down to the final 2-3 spots, it gets dicey. Pros and cons get discussed, but the hot mom card always wins out. Last year, we kept a kid on the team who had no business even making the team. Best part was that she is married to a then-current MLB player, and is a total smokeshow. I think the odds are good he makes the team next year too.”

How powerful is #hotgirlprivilege?

It even provides a penumbra of #hotgirlprivilege to others within the vicinity of the hotness. 

Also, I’m scared to even think about how often this same rationale is applied in high school sports with male coaches for girl’s teams. 

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.


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