Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

Apologies for missing last week’s anonymous mailbag, but with the late night LSU-Clemson game combined with a two hour flight delay on Tuesday morning to get back to Nashville, I barely got back home in time for the afternoon TV show, much less writing.

So we’re back this week with tons of splendid life advice for you.

All to help you mourn the end of the NFL and the college football season. (I know, I know the Super Bowl is still left, but that’s just one college and NFL game between now and late August.)

As always you can send your anonymous mailbag questions to, anonymity guaranteed.

So here we go:

“I’m a 22 year old senior college student at an SEC school.
I am a business student and did an internship at this great company that I loved working at this last semester (fall semester). My boss for this internship was a very attractive 35 year married woman who is high up in the company. We got along great during the semester and were very flirty at times with each other.
At the end of the semester we went out for drinks by ourselves and she told me she would get me a job at the company after graduation and help me move up the ladder if I would have a continual sexual relationship with her.
This company’s very hard to get a job at. So I decided to start sleeping with her. We’ve slept together probably about 8 times now over the last month. Her husband’s out of town two or three nights a week which makes staying the night with her very easy. After the first time I slept with her she already had me a job lined up for May.
My question should I be sleeping with my boss? Is there a negative side that can come from this? I mean I enjoy being with her, we have a lot of fun, the sex is great, and she’s also lined me up a good paying job and will help me advance. All these are positives but wondering if there’s something I don’t see? Is this something I should continue? Will things last or could this blow up?” 
First, she is risking WAY more here than you are.
She’s going to get fired if this ever comes out and, arguably, you can never get fired by this company. At least not without getting a huge severance. Honestly, aside from the fact that her husband might kill you if he finds out, it seems to me like you’re living the dream here.

I would say you have to watch out for her not actually giving you a job when you graduate and just using you for sex, but even if that happens what have you lost out on? Are you really bothered by being used for sex? I wish more women had used me for sex when I was 22.

Hell, I wish my wife would use me for sex more now.

So aside from the morality of your decision — which you don’t seem to be bothered by at all — and the potential that a jealous husband one day beats you do to death, I’m not sure what you lose out on here.

I do think this woman may well have a few screws loose because if she’s engaging in this wildly risky of a behavior she’s probably also engaging in other risky behavior as well. (In other words, as irresistibly sexy as you may find yourself, I find it unlikely that she’s been heretofore faithful to her husband and you’re the first time she’s stepped out on him.)

I also think she’ll probably tire of you at some point in the near future and move on to another conquest, so I think you have to be prepared to play it cool and not get emotionally entangled with her. But assuming you can do all of that, I’d say good luck on the new job.

(And also if you really want to protect yourself you’ll document all the evidence of her trading sex with you for a job so you are protected in the future if your job gets threatened over this situation. You were a young, powerless desperate and naive college student who had no ability to resist the craven, powerful boss who demanded your sexual consort. That’s how #metoo works, right? You might as well play it to your advantage and protection.)

“I am a 38 yr old single man with one son from a previous marriage who desperately wants to meet a woman and have more children. 

I met a woman over the holidays who I seriously think I am in love with. We match in every way and want all the same things in life….she wants to have kids, get married etc.

Here’s the rub….she mentioned that she would lose all respect for me and didn’t know if she could date someone who supports Trump in any way.  I laughed at first when she said it but then realized she was serious. I don’t think I am a hardcore Trump supporter, but I do agree with the majority of his policy & think he has been exactly what our country needs.

I actually lost some respect for her that she would feel that way about someone’s political beliefs, but I can’t express how crazy I am about her in every other way.  Some guidance on how to approach the subject with her would be greatly appreciated.”
First, you met a girl “over the holidays” who you think you are in love with?
This means, at most, that you’ve known each other for two months.
You should play a lot harder to get.
You’re a 38 year old man who desperately wants children. If you make a decent living and she’s around your age, her options aren’t that great, which means you should be a decent catch if you just act normal. What does act normal mean? Don’t be a 38 year old who falls madly in love after two months.
Again, I can’t state this clearly enough, there are way more women around your age desperate for children then there are men who want to be with them. You are working in a seller’s market, don’t undersell yourself.
Tell her you’re going to give her a massive engagement ring if Trump wins re-election, but if the Democrats win you’ll be forced to cut the size of her ring by 40%.
If she’s like most people, when the rubber hits the road and she sees a truly tangible impact on her own financial lifestyle, she’ll be less committed to the idea that Republicans are evil.
More seriously, tell her that you voted for Trump and might well do so again in 2020. Say you understand if that’s a deal breaker for her, but that her being a communist isn’t a deal breaker for you.
Women are attracted to confidence. Telling her exactly what you think is a confident move that she will actually, deep down, respect much more than if you grovel — or even worse — lie about what you believe.
The other option is just to say you aren’t really political and avoid the entire conversation. But with the 2020 election upcoming do you really think you’re going to be able to avoid the topic entirely for the next ten months? And are you going to secretly go vote for Trump like Tom Brady and tell your wife that you didn’t?
Good luck with that, but I’d just be honest.
“My wife and I have been married for 10 years, 3 kids and regular sex just like any other married couple except this one thing.  My wife is a squirter, like full blown porn star type squirter.  Which I admit, during our time dating and early marriage was awesome.  Now as I am getting older (late 30’s) its almost not worth the hassle anymore.  After she soaks and I mean SOAKS the bed, it’s a 30 minute process of changing the sheets and showering.  My question is this, do I tell her she needs to start trying to control this a little better?  Maybe saving the squirting for special occasions?  Or do I just accept the great sex and the 30 minute cleanup and move on?”  
Stop being a pussy and have sex in the shower more often.
Also, if you ever need to make extra money, I’ve heard some people like these videos, especially if amateur milfs are involved.
You might be sitting on a squiring goldmine, the sexual equivalent of the Permian basin oil field.
Hey, it beats having to save for the kids college fund.

“Clay, I’m a 22 year old college kid. 

I’ve recently started seeing this girl. Hot as hell, great and easy conversation, ambitious, funny… overall great girl. I could see this one really going somewhere.

When I first start seeing someone, I usually look them up on social media, and often stumble upon their parents as well. She had mentioned to me that both her parents were lawyers. Turns out that they’re very successful, having both graduated from top law schools and currently owning a law firm in California.
I honestly kind of find this intimidating. I usually pride myself on being able to talk with anyone about anything, but I really know nothing about law practice. I feel that I should at least familiarize myself with some of the details of law, so I don’t look moronic when I meet them.  
So, in your infinite lawyer knowledge, what are some things that not everyone knows about law that might help me impress?” 
Do you really think two lawyers want to talk about substantive due process with a 22 year old college kid?
There is nothing a 22 year old college kid is going to say about the law that impresses two full-time lawyers.
Anything you hit them with will seem banal and trite. What’s more, if they are like most lawyers, they probably would rather talk about anything other than the law.
If you really want to talk about their profession, ask broad and open-ended questions, “what’s the most interesting case you’ve ever worked on?” “What do non-lawyers like me get wrong the most about practicing law?” “Would you still go to law school if you were my age?”
Pro tip for everyone out there, regardless of what the parents of your boyfriend or girlfriend do, worry about treating their kid great, everything else will take care of itself.
I think that’s true whether their dad is the president of the united states or a garbage collector.
As someone with three young boys, I can tell you that most parents just want our kids to be with someone who makes them happy. (And ideally better versions of themselves).
That’s pretty much all I care about and it’s all you should be worried about too.
“My wife and I got married in Vegas. To set the scene, we didn’t invite anyone to the wedding, but rather had a reception in Houston and basically told friends and family, “This is the date we are getting married in Vegas, if you want to come, great, if not, we understand.”
Because of this we didn’t have a wedding party, only a best man and maid of honor (This will com up later). In the end, we had a nice turnout of 50+ people. Standard mix of family, college friends, co-workers and some HS friends.
This is where the story gets started. My friends and I went out and gambled/drank all day. Probably right at the line of too much. We leave the south end of the strip in a limo to the north end where the Chapel was located. About a 25 minute ride. As the guys are getting out my best man looks at me and says, “Dude, I forgot the ring.” “Haha, nice try…” “I’m dead serious. I think we got a little carried away. What do I do?” “Go get the damn thing.” Benefit of hindsight, we probably should have used a stand in, but whatever.
Anyways, we had to wait the 40 minutes or so for the limo driver to take him down and back. He gets back, we get married, all is well. Come to find out the next day, one of my wife’s HS friends was and always had been in love with her. They never dated in any capacity. He just always had this secret crush. He sits in the second row, on the aisle fulling intending on objecting to the wedding. He tells the person sitting next to him of his grand plans. He didn’t know, but was sitting next to my sister!!! She obviously would have been in the wedding party had we had one… She explains who she was and how dumb his plan was and he decided against objecting to our wedding.”
And then he banged your sister instead.
That’s how this story should end, anyway.
I still would love to hear, has anyone ever been at a wedding where an actual objection happened? I’ve been going to weddings and hoping for this my entire life.
Still haven’t seen it happen. Even crazier, I haven’t even heard of anyone else having seen it happy.
This is like the white whale of wedding stories.

“Love your show. Really impressed at how much energy you have, and your insightful perspectives.

Perhaps a situation with which you have some experience …

As a small business owner, I have been fortunate enough to grow my business to the point where my personal net is about $1 million annually. I have five people who assist with my endeavors – bookkeeping, website maintenance, IT, generating reports, etc. Although they are paid about 10% above the local average for their professions, it is significantly less than my income.

What do you think a good Christmas/year end bonus would be for these people? Whether it is $1k, $5k $10k,$? … each of those sends a different message, so I am not sure what is best? Your thoughts & insight would be greatly appreciated.”

It’s late for this, but I think a Christmas bonus that’s around two weeks pay seems like a nice thank you to your employees.
If things are going spectacularly well then I think you could give more than that, but the challenge with bonuses is once you give one people expect that amount going forward.
They might say they don’t, but they really do.
So you need to give an amount that you’re sure you can afford to give the next year and the year after as well.
I’ve never in my life gotten a Christmas bonus from any employer for anything, but I try and give people who work with me daily at Outkick a little bit extra over the holidays.
I think it’s a nice thing to do if you have a successful small business and think someone’s work deserves a bit more.
Send your anonymous mailbag questions to claytravis@gmail, anonymity guaranteed.

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.