Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

But before we get rolling with the anonymous mailbag, it’s time to get your financial house in order with my guy Ryan Kelley at The Home Loan Expert. Right now, in the month of April, if you sign up for a mortgage and close out the process, I will give you a free room and passes to Outkick the Weekend. So why wouldn’t you act now? Go prequalify, refi, or get a brand new mortgage today.

Okay, here we go with the anonymous mailbag.

“I am in my buddy’s wedding coming up this summer and I (and him) need your advice. Six months ago we got in touch with a bookie and opened a joint account (now I know this is a beta move, but we both couldn’t get an individual one because my buddy is not known in the local gambling setting. I figured what the hell, what could go wrong?)
Now on this account, we were gambling on credit. (see where this is going?) Football season was good until my buddy had $1,500 total on the Steelers to beat the Jags in the playoffs to win $500. The Steelers lost and after that my buddy kept going big bet after big bet and eventually got down $9,700. I was up $2,200, but the account was down and it was time to pay. (We set our credit limit at $7K, $3,500 a piece). 
He has money in his account, but that account is also being watched by his soon to be wife like a hawk. So he gathered up spare cash, took $4,000 out of his account, and I spotted the rest ($3,200) because I’m single and can make bad decisions without answering to anyone. So my buddy tells his fiancee that I am the one who has the gambling problem and he loaned me $4,000 to square up with the bookie. This is the only lie that he could think of in a short period of time. So now I am owed $3,200 by my buddy and his fiancee thinks I owe them $4,000, a $7,200 swing in change. If my buddy’s fiancee ever found out the truth, the wedding would be 100% off. My buddy makes good money but he can’t get it out of his account cause his fiancee will notice. 
So my question(s), how do we embezzle the remaining funds out of his account to get back to even? Or do we? Do you think she will ever find out? If I never “pay them back,” will I ever be able to chase local women because I’ll be the town degenerate broke guy? Thanks in advance. (I have learned my lesson Clay, don’t worry).”
First, your buddy is a total pussy. If he’s already got his fiancee monitoring his private bank account before they even get married then his life is fucked regardless.
He shouldn’t have to justify any expenses on his account to a woman he’s not even married to. And if he’s making all the money he should be able to spend it however he sees fit regardless of what she thinks, especially before they are even married.
Seriously, I already feel bad for this guy and he has no idea the hell his life is going to become if his fiancee is already this controlling. So a huge part of me just wants you to tell her the truth and blow up their wedding. (The truth of the matter, unfortunately, is that she won’t actually call off the wedding over this. He just thinks she will. And that’s why she has him by the balls, because he’s been a total pussy on situations like these and not called her bluff before. Plus, if she did call off the wedding, who looks worse here, your buddy who lost a few grand gambling on sports or the bridezilla who I bet is spending at least $20k on her wedding and called it off because her boyfriend lost a few thousand dollars gambling? As you say, he makes plenty of money so it’s not like he’s losing money that is leaving him in the poorhouse. There’s no way she’s actually calling off this wedding.)
But I understand you probably can’t blow up the wedding and feel good about yourself.
So your buddy has to pay you back and I think the only way he can do it is via embezzlement from his own bank account. So what I’d suggest is that he try and get you $100 a week. He could probably smuggle that money out via checking withdrawals without being captured. He needs to withdraw the same amount weekly in cash and keep it coming that way, a $100 a week to you until he’s paid back his debts. The downside here is that takes a long time to happen. (If she’s going to look at his ATM receipts and compare that with his credit card charges to catch the discrepancy his life is seriously over.)
The other option here, and I actually prefer this one, is to withdraw $5000 — he could still pay you the rest in withdrawn $100’s over time — and give that money to you. When she inevitably complains about where that money went he should lie and tell her it’s for the final payment on her wedding ring. That way this awful, controlling bitch actually thinks he spent more on her wedding ring than he actually did. That way at least his lies end up benefiting him. (He could also lie and say the honeymoon was more expensive than he let on, but then she may go back through those billing receipts and catch him in that lie.)
The biggest issue I can see here, aside from the fact that he is marrying an awful woman and can’t just tell her the truth about his gambling losses, is that your buddy has to get way better at lying. He should have come up with an entirely different story — the wedding ring for example — beforehand to avoid throwing you under the bus for his gambling debt.
In the event this gambling debt rumor about you being a derelict spreads, you can feel free to say that isn’t the truth, that you were paying his debt because he was afraid to admit it to his fiancee. That story may eventually get back to her, but so what? You aren’t obligated here to keep lying to cover for your buddy’s stupidity. Especially not when a girl might be impressed by your loyalty.
“I live in South Florida and even though I’m 28 now I still frequent the spring break spots during March to enjoy the sights. This year I hooked up with a stunning 19 yr old, easily top 3 girl of my life. She’s back up north now and we’ve been texting a bit, so I decided to entertain becoming a young sugar daddy and offered to fly her down this summer for a weekend. She seems pretty open to the idea.

Now I don’t care about shelling out $1,000 for a weekend full of sex with a hot college girl, but do you think it’s worth 4 odd months and countless hours of chatting this girl up to keep it going until the summer? She’s single, but that could obviously change at any moment and there’s no realistic dating possibility for us. Then again, I may never get a girl this hot again in my life and she certainly wouldn’t hurt my chances with any girls that I know that happened to see me hanging out with her. Thoughts?”
Is this a real question?
Of course you keep things going and bring her back down for a visit.
How valuable is your time that you can’t do a little text work to keep a smoking hot college girl entertained in exchange for great sex for a weekend? Plus, there’s the potential you could sugar daddy this thing for the next several years. And how much would you pay to have sex with her if you were just paying for sex? (Not that you would ever value a woman entirely for sex. I’m sure you and the 19 year old also have great intellectual conversations.) At least a grand, right, since that’s what you’re willing to pay her to come visit.
No brainer here.
Short of you getting her pregnant, I just don’t even see a way this scenario turns out badly for you. Sure, she might decide she doesn’t want to travel back down to South Florida and bang the old dude anymore, but what do you care? She already banged you once, odds are she’ll bang you again. And again, and again, and again.
And all of you have to do to make this happen is text or Snapchat with her? Get the fuck to work and stop asking stupid questions.
“My girlfriend cheated on me. I always said that I would dump my girlfriend and never look back if this ever happened to me. I always thought people were stupid that went back to their significant others who cheated on them. Once a cheater, always a cheater was something I was firm in believing. Now, I am torn.
I found out last week that she cheated on me. We have been dating for 9 months, talked about moving in with each other, etc. She claims that it only happened one time like the second month we started to date. She was drunk and stayed at her friend from college’s house when she was back in the college town one weekend. She said she doesn’t remember much of the night, but remembers having sex with him. She said she regretted it and it didn’t mean anything to her, but she couldn’t tell me because she knew my stance on cheating.
The kicker here is that she continued to stay at this house (other guys live there too) other times she was back in this college town. She said nothing happened again, but she didn’t want to ruin her friendship with this guy or the other guys. The other huge kicker here that the only reason I found out about this is because I had a weird feeling and looked at her phone. I felt bad for going against her back and looking but I had to do it. I found texts from the week before with this guy. She stayed at this guy’s house again that weekend. He texted her about how he wished they would have done something like that other time. She kept denying him and saying she couldn’t because of me. He kept going and then she eventually replied that she wished they could fuck on her car. 
She has been hysterical ever since I broke up with her. She hasn’t gone to work and keeps asking me for a second chance. She says she only had sex with him while we were dating the one time. She also says the text messages about fucking on her car was the only time she did that. I want to believe her, but I am torn. Half of me wants to give her another chance, and the other half wants nothing to do with her. King Solomon of the Internet, what should I do?”
“My girlfriend didn’t tell me because she knew my chance on cheating,” is one of the all time dumb things people in relationships say. Are there people out there who have a stance on cheating that is favorable? Is there anyone out there like, “Yeah, I told my girlfriend, just bang everybody that walks and don’t tell me anything about it at all!”
Of course your stance on cheating is don’t cheat and of course your girlfriend knew this.
I have very few ironclad rules in life. But one of them is: If your girlfriend texts another guy that she wishes they could fuck on her car — after she already fucked him while the two of you were dating — you have to break up with her on the spot.
The fact that you are emailing me asking what you should do is proof your balls have been chopped off. Or you’ve lost them.
So let me help you find them.
How can you do this?
By banging this girl on the hood of that guy’s car and then dumping her once and for all and never talking to her again.
Trust me, revenge is a dish best served on the warm hood of someone else’s car.
You’re welcome.
“So my buddies and I were talking the other day and one of friends who happens to be gay and live in NYC, admitted he jerks off 3x a day! In the morning, lunch hour, and after work and also said after work one day him and his boyfriend got off 3x just that evening! Of course, our minds immediately went to the Wolf of Wall Street, but this seemed excessive.

Is this psychotic behavior? 3x per day seemed crazy to us. I don’t even know where he gets this much sperm! I am married and my wife and I have sex 3-4x/week. Other buddies admitted to jerking off maybe 3-5x/week as well. But 3x per day?! Can we ever trust him again?”
I think jerking off is a function of age.
If you’re home from school for summer, are 14 years old, and aren’t jerking off three times a day I don’t know what you’re doing with your life.
But if you’re 54 and you’re jerking off three times a day, I don’t think you can be trusted.
Seriously, if I found out that my accountant — today is tax day, hooray! — was jerking off three times a day I would switch accountants. Just can’t have it. But if I found out that Sam Darnold, for instance, was jerking off five times a day and also having sex five times a day, whereas Josh Rosen didn’t masturbate or have sex on a regular basis, I’m taking Darnold. (Or Rosen if the situations were reversed). I want my QB1 to have a dick like a goddamn helicopter. Just swinging it around all the time at a moment’s notice.
That’s a Super Bowl dick, a guy who can perform under pressure and make plays.
In general, however, jerking off, to me, is a function of how much free and/or solo time you have in your residence. For instance, when you’re in college, you have to time your jerk off sessions to when your roommate is out of the room, but you have quite a bit of time to jerk off. Then when you’re a single guy living alone — or with your own bedroom with a door — you can jerk off all day long and no one cares. But eventually you get married and may have kids and then you have to restrict yourself because you don’t want, god forbid, your wife or kids to walk in on you treating your body like an amusement park.
That’s especially the case when your kids are old enough to remember what they saw forever. Can you imagine walking in and seeing your dad jerking off? I honestly don’t know how you recover from this. It’s much worse than having a kid walk in and seeing you having sex with your wife. That’s nightmare fuel for life, the kind of thing that turns you into a beta male social justice warrior.
I’m not forty yet, but I can’t imagine what the standard is on old man jerk offs. Once you’re a grandpa you can’t jerk off more than once or twice a week, at most, right? And you definitely can’t get caught by anybody then.
Anyway, if you’re in your twenties, you got to keep the pipes clean. Same thing with the thirties. After that, you should be too busy to jerk off three times a day.
“Heard your take on the Starbucks thing yesterday on your Periscope. Something that has been overlooked: As you mentioned, we’ve all been in the situation where we or our kids need a bathroom, usually quite urgently.  So that’s allegedly the deal with these two guys.  They are told you can’t use the restroom unless you’re paying customers.  Speaking for myself, if I need to take a desperate whiz I’m either going to buy something or go to another place.  What’s not going to happen is I go to Starbucks, ask to use the restroom because I have to go really bad, then when they tell me no I’m going to sit around for an hour holding myself. No way.  Something fishy about this.  But since Starbucks is a bunch of pearl clutching progressive snowflake pussies, I hope they get their asses kicked.” 
Yeah, this story doesn’t make sense at all.
I have been in a ton of establishments over the years where an employee has told me you need to buy something to use the bathroom. (That’s when the bathroom door is locked and you can’t just walk in and use it first, which is very common in big cities or, interestingly, shitty Southern gas stations.) I’ve also been in these situations with one of my kids, where they have to use the bathroom and you’re just hoping they don’t pee all over themselves while you’re waiting for the key or the key code to use the bathroom.
Do you know what I’ve done in every single one of these situations when I was told that the bathrooms were for customers only?
(I have also pulled over on the side of the road a ton of times when this situation has happened on long trips, yanked open the door, and let my boys pee out on the side of the road while other cars are driving by and the kids are spouting off like firehoses so, admittedly, I may not be the most normal person out here. I’ve also said, without fail, something like this after each of these emergency urination stops. “Kid’s got a good stream going, strong pipes. Good genes. Bodes well for the future.” And my wife just rolls her eyes.)
My point is this if you really have to use the bathroom — or your kid does — paying a couple of bucks to buy something you don’t want is a small price to pay to use the bathroom.
Have you ever set down for good poop or pee — when you’ve just rushed into the bathroom and had to go badly — and not thought, “By God, this feels so good I would have paid $20 for this.”
So why would this guy have to use the bathroom and then choose to just sit there and piss or poop his pants rather than buy something and use the bathroom? It’s a good question. And then on top of this he goes to jail? If you really had to pee or poop would you risk peeing or pooping all over yourself in the back of a patrol car on your way to jail?
That’s why this feels like a set-up to me. Like they might have known exactly how this manager would react and they wanted to set up a viral phenomenon to force Starbucks to end up paying them millions of dollars to make the story go away. Maybe the manager was racist and hated black people and his employees knew and they set him or her up. (Do we know anything about this manager at all?)
Because while I understand saying that restrooms were for paying customers — which is a rule that really exists in big cities to keep homeless people from using the bathrooms all day long — I also don’t understand why you would call the police over this situation if you managed the Starbucks. There had to be something else going on here, right?
But even considering all of that, who chooses to go to jail — WHEN THEY ALREADY HAVE TO GO TO THE BATHROOM — instead of leaving a business when you’ve been asked three times to leave? The only way this makes sense to me is if getting arrested was all a part of the plan to extort Starbucks.
And don’t even get me started on the fact that this entire scene was filmed too.
I’m just not buying it.
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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.