Anonymous Mailbag

As you can see, Outkick version 3.0 is in the process of being rolled out. You can now easily search for any article that has ever existed in the six year history of the site by date on the lower right side of the screen. And you can easily search for all the anonymous mailbags by just typing in the search query on the right side.

For instance, here are all the anonymous mailbags.

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Speaking of which, I’m headed to the beach on Saturday and I’ll be working from down there for the next two weeks. And I’ll be staying in an incredible beachside mansion for all two weeks. If you want to do the same — and why wouldn’t you? — check out my friends at Mention Outkick for 5% off.

Okay, here we go with the anonymous mailbag:

“Clay, I need your help. I feel one of your skills is that you can make the most out of any situation, and find a way to put a good spin when he circumstances are dire.

My boss’ boss’ boss is a former collegiate swimmer at an ACC school. He’s in his mid forties but is built like a prototype swimmer (6’4″ 190), still swims weekly, and is in very good shape. He’s also the most intimidating person you’ll meet. Rarely smiles, has a Mr Burns brooding way about him, stares off in the distance while he consternates on who to fire, prefers cats to dogs – you get the picture.

I’m 31, but I feel more like a brisk 27. I go about 6’2″ 270 and have the body of an upside down slice of pizza (crust down), which conveniently enough, is the majority of my diet. In my day I was a good athlete, but I’ve never done any competitive swimming (more below). I work out regularly but I wouldn’t say endurance is my forte or that I’m in “good shape” – although you’ve likely already come to that conclusion based on the whole 270 lbs thing.

Last week, I was talking with several coworkers including the swimmer boss – we were chatting about a variety of topics including our current work out plans and our degenerate gambling issues. I’m really not sure how I ended up on the warpath, I kind of blacked out a little bit, but when the dust settled it ended with me betting a significant sum of money that I could beat the swimmer boss in a 100m race. In my mind swimming is not that hard, 100m is not that far, he’s old and I’m relatively young, and frankly I just felt confident and willing to bet on myself.

Here were the agreed terms and handicaps – I get to swim 100m, all freestyle. He has to swim a 100m individual medley – but he has to swim in this order: 25m breast stroke, 25m back stroke, 25m butterfly, 25m breast stroke. No freestyle for the boss. In college he swim the 100m IM in under a minute. Within 10 min of booking the bet I realized I had made a huge mistake and began to look for exit strategies.

Right now, I’m having a hard time finishing 100m freestyle in under 1:35. On top of that, I ran my mouth in front of half the office so I can’t crawfish out of this bet. My coworkers are ravenous and have been foaming at the mouth since it happened. A coworker has reserved a pool in his neighborhood and is catering a meal for 20 coworkers to watch my destruction this Friday.

What’s my move here? I have a lot of points of exposure:

1. I’m not emotionally prepared to tuck my overflowing ass into a tight swim suit in front on my coworkers, but I feel like the right speed suit could both tasteful and could help with resistance in the pool. 2 birds one stone.

2. I’m going to lose. I’ve accepted this. The day after I made the bet I walked into the boss’ office and tried to buy out of this bet. He told me “I’m going to teach you a very expensive and painful lesson” while laughing maniacally. It was the happiest I’ve ever seen him. Yeah, so I’m going to lose.

3. My wife doesn’t know the bet I’ve made and will likely wear me out when she finds out. I give her crap all the time about spending too much money on shoes and clothes, so I don’t expect her to have much grace with me in this situation.

4. Is there a respectable way to lose or bow out? Do I fake an injury? Do I “Tanya Harding” my boss 3 levels above me? This seems like my best bet. I’m very conflicted.

Please advise.”

No one likes a bet welcher so you can’t bail out here.

I think your only play here is to go full speedo and play your bet for laughs. That doesn’t mean you intentionally tank the race or anything — you do your best — but you play it for laughs. If you wear a speedo, everyone in the office is going to love you because you’re the fat guy in a speedo.

If you show up in a regular swimsuit and lose, it’s like you’re trying to hide how ridiculous this situation is.

Take it from me, you’re always better off just owning absurd situations.

Think of it this way, the fat guy who wears his shirt in the swimming pool isn’t fooling anybody. No one’s like, “Man, I didn’t know Tim was fat when I saw him every day in his regular clothes, but then I saw him at the swimming pool and turns out the guy’s a total fat ass.”

Everyone knows if you’re fat and you might as well just be the fat guy.

As for losing all the money, there’s no way your boss’s boss’s boss is ever going to let you get fired now since you’ve given his life a newfound purpose. If he allows you to be fired, that’s just cruel and inhumane. He beat you in swimming after you wore a speedo to the competition and he fired you too? So whatever money you are losing here is really job insurance. At least that’s how I’d spin it to my wife.

Also, in the event Mr. Burns is truly evil and does decide to fire you, technically you’re illegal gambling and the company is endorsing it. So if he tries to fire you, you’ve got something on him.

So good luck, Fat Phelps. (By the way, if you got Fat Phelps put on the ass of your specially made speedos, you’d win the bet no matter how much money you lose. Do it!).

“Background- happily married, two kids, normal married sex life.

My wife goes out with the girls last week and gets nice and sauced up. Gets home ready for business. She asks to turn on some adult videos and then tells me she wants to have a 3-way that night. This isn’t the first time she has talked about this when drunk, but this time she goes so far as to have me download Tinder while she downloads some other app. After a couple hours it doesn’t happen and we pass out. I try to softly bring it up a couple days later and she gets defensive and doesn’t want to talk about it. So what’s the play? Is this a good idea to begin with? Obviously is sounds like a great time, but there could be unintended consequences. Or maybe it is a blast and opens a whole new door. We do have a hotel Memorial Day weekend. Also, do you try and pick a chick up or go the back page route to try and minimize jealousy?”

I think you hire a hooker and go with a professional to start with. You don’t have to tell your wife you hired a hooker, but you probably should. You can even dial up the fun and have her pick the girl. Now the risk here is, what if you try and hire a hooker who is actually a cop? Can you imagine getting busted for soliciting a prostitute to have a threesome with you and your wife?

Has this ever happened before? Have a husband and wife been jointly busted for solicitation? This is the only way for a guy to get arrested for prostitution and end up looking better than he did before he got arrested for prostitution. “You hear about Doug? Got arrested for hiring a prostitute…with his wife! They were going to have a threesome! She picked out the hooker and everything! How hot is that?!”

I’d love to be the lawyer defending you in this case, “Ladies and gentlemen of the jury, is it a crime to be awesome? Because that’s exactly what my clients are accused of here. Being too goddamn awesome.”

So here’s what I’d advise — go to Vegas and do it. Have her pick a girl out the next time she’s drunk and then reserve that girl for your trip to Vegas. That seems like the safest option because you never have to see that girl again. What was it Charlie Sheen memorably said, “I don’t pay them for sex, I pay them to leave.”


I’ll admit to being out of the game here too. Surely the world has not become so awesome that married couples can easily go on Tender and find smoking hot third wheels to be in threesomes with them within a couple of hours, right? It can’t be that easy, can it?

Because I swear to God, I am already jealous of the sex lives my three boys are going to have when they get to college. They’re nine, six and two and they have no idea how hard their dad used to have to work to see a naked boob in Playboy. “Do you kids even know how many times your dad jerked off to scrambled Playboy on standard definition TVs? Did you know there used to be late night USA Network programming called “USA Up All Night,” where the entire programming strategy was built around giving 14 year old boys masturbatory material? And now you spoiled ass kids have naked girls everywhere. You don’t even know how good you have it. Stop bitching about anything in your lives. Everything is perfect.”

Anyway, we need an update on how this goes.

Lots of you are demanding anonymous mailbag updates so I’m going to make them a substantial part of the anonymous mailbag going forward. What I’d ask is I feature you in the mailbag with a question, that you please email me an update when your situation has been resolved.

“A week ago this girl I’m talking with and me were chilling at her house. Her phone died and she needed mine to use one of her social media accounts. I figured she logged out and didn’t think anything of it. A few days later I open up my app and her profile pops up and it’s logged in on her account.

I’ve had trust issues with her in the past and so I decide to just check her dm’s to make sure there was nothing there. I open them up to find her getting all these sexual messages from these guys and her not shutting them down. Then I see she’s sent some provocative photos to one person in particular. My question is, do I confront her about this or dbap and not say anything to her? Or am I just weird for checking her dm’s?”

You break up with her.

But not before having a nice couple of final sexual romps.

I don’t see why you need to explain yourself here. She’s cheating on you and you have pretty solid evidence of that fact. Did you violate her privacy by checking her DMs on your phone that was left logged into her account? Sure. But the vast majority of people reading this right now would have probably done the same thing given the fact that she stayed signed in on your phone. And you confirmed your suspicions that she was cheating on you in the process. No need to give her a reason, just say the relationship isn’t working out for you.

“A few days ago I was approached at a local bar by a women, solid 9, she had a tattoo sleeve which automatically gave me that hot crazy chick vibe, plus the fact that her nipple rings poked through her shirt, let’s just say I was mid chub from the moment she walked in. She had such a white trash name I couldn’t decide whether to give her a fake number or just take her to my jeep outside.

Anyway not even ten mins after I leave the bar I get a full on nude from the girl at the bar with the caption “cum over” and a pin location. Needless to say I put the pedal on the full. I pull up to her house, which wasn’t a double wide trailer surprisingly, and grab a roll of condoms ready for a wild night. Long story short the girl was an absolute freak in bed, she was like five years older than me and could have been a pornstar at some point in her life, but damn she knew what she was doing. The next morning rolls around way too early so I head to the kitchen for some coffee butt naked, morning wood and all when I feel someone tap my lower back I flip around real quick to find like a 6 year old child standing there, luckily I’m not packing like Ron Jeremy or I would have put the kid’s eye out.

Turns out she had three kids who had been in the house all night while we had rough, loud sex. Which brings me to my question. Is it okay to hook up with women under 30 that have kids, and if so in what scenario is it acceptable to make the kids listen? That’s really been weighing on my mind and conscience the past couple days, like if that kid grows up to be a serial killer I feel like I’m partly to blame. Plus the chick has been calling me nonstop wanting to hook up again but every time I picture that little boy staring up at me.”

Why can’t you just have her come to your place?

If she can’t afford a babysitter, offer to help pay for the babysitter.

Voila, problem solved.

Also, and maybe this is just me, but I think the mom was obligated to tell you that she had three kids at her place before you started banging. I’m not an expert in early childhood development, but it can’t be good for the emotional development of her children to start off their days staring at halfies from strange, naked men that just banged their mom all night long.

Further, this woman has three kids. Do you know who the dad is? Are you sure she’s not married? The last thing you want to do is get murdered by some Navy Seal when he comes back from overseas and finds out you’ve been banging his wife while he’s trying to kill all of Bin Laden’s sons.

So do your research here.

And as a general rule if I were a single guy who had never been married, I wouldn’t get involved with women with multiple children. It’s just way too complicated.

“I recently turned 26 and for the first time in my life had a moment where I met an 18 year old girl out at a bar and my first thought was not that she was hot but she was young. Don’t get me wrong she was hot but my first though was she’s too young for me to realistically have a shot with her so I kinda moved on to her older sister who was nowhere near as hot. Since you’re kinda old now I figure you can help me out. Am I weird for thinking that or is there a point where you just realize you don’t have a shot with hot 18 year olds anymore? I’m not sure I’m ready to enter that phase of my life.”

In general, there’s a good formula to apply here. You divide your age in half and then add seven years to find out whether you’re being a dirty old man. You’re 26 so this would mean you could date girls as young as twenty and as old as you wanted to go.

Now I’m not convinced this rule applies in an ironclad fashion, but I’d think most 26 year old guys wouldn’t want to date 18 year old girls. Unless that 18 year old is a 12 or higher on the traditional scale of 1-10. As always, #hotgirlprivilege can cancel out just about any male intentions.

I’m 38. This means when my wife leaves me — because I would never leave her — I can date girls who are half my age plus seven years without it being creepy. This would mean I could date women as young as 26. But as a practical matter I would be willing to date any girls who were 21 or older and extremely hot. And by “date” I mean “have sex with.”

Would people judge me for being 38, a father of three, divorced and “dating” a 21 year old who was born when I was a senior in high school?


But would I care?

Of course not.

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