Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag!

You can win $10k playing Outkick’s college football pick’em this weekend. It’s free and ready for you to play, just go click here.

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

Here we go:

“Last Saturday I was in Tunica playing craps and I saw something incredible, and by incredible I mean incredibly bad. My rule playing craps is you never bet against the old man at the end of the table. This was one of those times where my rule paid off.

After going on about a 30 minute roll, he has hit all the numbers except for the 5. If he hits that, he hits the all-tall-small bet which pays 175-1 for the ALL, and 35-1 for the tall and small numbers.

Then all hell broke lose. He had been complaining about his chest the whole time, but everyone kept encouraging him to keep rolling because he was winning. So on this roll he literally drops to the floor while throwing the dice across the table and hits the 5 in a weird manner.

(By weird manner I mean he collapsed as he was rolling).

After throwing the 5 in this manner and winning me almost $9,000, the floor guy ruled it a no throw. But then they entire table erupted and they eventually ruled it was a throw.

The whole time this old guy is having what appears to be a heart attack on the ground. (I’m still not sure if he’s alive or dead).

I ended up putting all my winnings on Alabama -31.5 vs Arkansas for a nice double up. The question is: Am I going to hell because I still have no idea what happened with the old guy?”

We definitely need video of this incident.

I wonder about this sort of thing all the time, what’s your obligation when something bad happens in front of you? Last year at the Super Bowl they played a prank on me where one of my radio guests appeared to have a heart attack. I was live on air and my immediate reaction was to just toss it to break.

Then I was going to get him help as soon as we went to break.

Here’s video of that prank live on radio row at the Super Bowl if you haven’t seen it before.

I don’t know CPR, what am I going to do for this old guy? I do know, however, how to toss it to break and figure out what to do during a several minute commercial break.

So that’s what I did.

Other than call 911 I’m not sure what to do with the guy having the heart attack at the craps table.

This would be, by the way, a phenomenal “Curb Your Enthusiasm” episode.

So you may, indeed, go to hell.

But it probably won’t be for this.

“So I am a 28 year old (professional job redacted). I am dating a woman who is a bit older than me. She is 43. We’ve been dating for 3 years now. She’s super hot for her age and she’s never been married. She has the same professional job as me. We have such an amazing time together, have a lot in common, and the sex is absolutely amazing. I want to spend the rest of my life with her but am having a hard time getting over the age gap. Do you think this is something I should worry about? Should I marry her? How should I go about this?”

I’d worry less about the age gap here and more about the life expectations gap.

In particular the big question is this: do you want kids? Does she? If so, then you needed to be trying to have kids five years ago. If not, that’s fine, but it’s something you need to contemplate.

I don’t think this is something most guys your age think about because it doesn’t impact you very much. After all, you don’t have a ticking biological clock. But if you’re going to get married to this woman this is a truly legitimate issue you’d need to contemplate in a serious manner.

The other issue you need to think about is this, in ten years you’ll be 38 and she’ll be 53. In twenty years you’ll be not that much older than she is now, at 48, and she’ll be 63, a senior citizen. This age gap continues, you’ll be 65 and she’ll be 80. Up unto the point where she’s likely to die well before you are.

In other words, it’s unlikely you’ll truly be able to grow old with her.

Right now you’re kind of at the perfect age where she can still be hot and you can still be in to her even though you’re much younger. But is that going to still be the case in a decade? I have my doubts.

Here’s the ultimate breakdown: if you date her for five more years and don’t get married, you’re still just 33 and haven’t really forestalled any life ambitions. But she’ll be 48 and still be unmarried. Is that her preference?

Honestly, she should be the one emailing me asking questions, not you.

She has way more at stake in this relationship than you do.

Your life is fine right now, why do you need to complicate it any further by marrying someone 15 years older than you? I’d just keep doing what you’re doing now.

It’s possible this woman doesn’t really want to get married or have any entanglements in her life. Trust me, she thinks way more about you being 15 years younger than her than you do. It’s possible this is a conscious choice for her.

But rather than change anything, I’d just keep doing what you’re doing now.

“My wife loves shitty low-budget Christmas movies. She admits they are poorly written and predictable but will still manage to DVR and watch 30-40 movies over the next two months. We have multiple TVs but I will inevitably get dragged into watching some and I don’t think I’m the only guy in this situation. The reason I am writing is to ask for your endorsement on my petition to the good people at Hallmark.

I’m simply asking them to please add some boobs to their films. I’m not talking about anything x-rated, just 2-3 scenes and/or 6-8 boobs per movie. This boob ratio didn’t turn women off of Game of Thrones so I don’t think it will affect their viewership here and it’d be a nice surprise for some of the straight males being encouraged/forced to watch. I know I’m not the targeted audience and they don’t need to cater to me, I’m simply asking they throw me a bone here.” 

I know these Christmas movies are insanely popular with women because I’ll occasionally walk through our house and find our nanny and my wife glued to these movies. It’s like women can’t look away when these movies start playing and they become completely transfixed by them.

Doubtless there are many men who get drawn into them as well.

I, however, am not one of them.

I’ve never watched more than like three minutes of any of them. But I am sympathetic to your quest since I’m obviously pro-boobs in all TV programs — including the World Series — but my question is why would you let yourself get sucked into these programs at all?

I get to watch so little non-sports TV that I worry about wasting my time on crappy TV. So why wouldn’t you just bail the minute you realize what your wife is watching and watch something else that you like more?

That program could, hopefully, include boobs.

Rather than try to change something that isn’t made for you, why not just embrace the programs that are made for you?

(I also disagree with you on the boobs. The average 65 year old grandma watching this program would have a stroke if suddenly boobs showed up in her in Christmas Hallmark movie. I do, however, think this would be an amazing prank to pull off once just to see the reaction. Like if there was just a raunchy “Game of Thrones” style sex scene mixed in for one minute of one of these movies. What happens?)

“This past weekend I went to a Halloween party in Atlanta and I wore a “Make UT football great again” hat to the party. I walked in and saw a good friend from college at UT so I went over and sat on the couch and caught up with her. She ends up asking me about my hat; I told her I thought it was funny because we sucked for 10 years.

She kept asking me if I voted for Trump. I did vote for him but I’m constantly surrounded by extremely judgmental liberals in Atlanta that will shame you publicly if you make any sort of a conservative comment so I just kept trying to side step her questions until I felt like I needed to just say I did vote for him.

I then said, but I respect you opinions and you’re entitled to them. I even understand why you think some of the things you do. To me it’s about something different, I don’t hate anyone, I don’t want anyone to leave our country and I’m pretty okay with people doing whatever they want in their personal lives as long as it isn’t harming others” she said “oh so it’s about money?” Then she went on another rant about all this. I eventually leave the party but here is where the biggest issue comes.

My best friend who was there was singled out for being conservative (like it’s this big taboo) by a liberal friend as a joke while the party was winding down and they were getting in Uber’s to go to the bar. Everyone was laughing but then when the Uber got there this girl decided to throw a fit and say he couldn’t come to the bar with them or ride to the bar because he was a conservative.

The girl ended up not coming to the bar. 

Your thoughts?”

The girl is a total diva.

Like many young boys and girls before her she wanted to draw attention to herself and she’s decided to make herself a martyr in the process by overreacting to a minor difference.


It’s just so transparently stupid it would be laughable if it weren’t so commonplace today.

She was probably also drunk, which aids in the drama, but if anything, people like her make me want to be a diehard Trump supporter. Left wingers have so lost their minds over Trump that being a Trump supporter is the rebellious thing to do. Remember back when left wingers were rebels? Now they’re the thought police — if you have any thought that steps outside the bounds of acceptable opinion they come after you.

It happens every day all day long on social media.

I just don’t get this girl’s rationale at all and I suspect most of you reading the anonymous mailbag don’t get it either. I cannot imagine any political belief a hot girl could have had when I was in my early 20’s that would have led me to refuse to share a cab or go out drinking with her.

If a group of smoking hot girls thought white men were the devil back in 2001, but I thought they were willing to sleep with me or one of my friends, I wouldn’t care if they thought white men were the devil, I’d drink with them all night in an effort to sleep with them.

I had a crazy idea back then and I still have a crazy idea today: what someone else believes doesn’t impact what I believe.

I’m fine hanging out with people who disagree with me on a variety of topics. Hell, that’s actually more fun to me than hanging out with people who agree with me on everything.

But the important point is, I just don’t think what other people believe reflects what I believe.

Now you can say that makes me an awful human being — how dare I be willing to hang out with people who think completely differently than I do?! — but I think that mind frame would have accurately characterized every guy I knew back in 2001, regardless of race, religion, ethnicity, any sort of identity.

I don’t remember ever hearing a straight guy say he wouldn’t sleep with a hot girl because of her politics or because of any belief she had.


For any issue under the sun.

Hell, I remember one of my buddies, a minority, saying he thought he could bang the racist out of any woman. (Which is an incredible line, but also symptomatic of the way we thought back then.)

Now I’m not saying things were dangerous way back in 2001 in America, but it was much, much more dangerous by every statistical measure in 2001 compared to today. Rape, murder, robbery, every crime was much higher in 2001 than it is today.

And the issues confronting our country were much bigger back then too.

That is, the stakes involving our country, particularly after 9/11, were far more perilous and complex than anything that we face today. As if that weren’t enough, the 2000 election was far more contentious of a national battle than anything that happened in 2016.

Yet everyone was totally fine with everyone else when it came to hanging out, regardless of their politics.

No one was refusing to share a cab with a George W. Bush supporter and there was way more difference politically between the decisions being made by Bush and Gore than there is between Trump and Clinton.

This girl’s behavior is just ludicrous.

The best way to get back at her?

Hook up with her and then when you’re leaving her place the next day say just before you leave, “I had such a great night, I made a donation to Donald Trump’s 2020 presidential campaign while you were sleeping beside me. You’ll get a hat and some bumper stickers later this week.”

(And, by the way, I would say to do the same thing if you hooked up with a Trump supporter and he or she was arguing about how Bernie or Warren or Kamala would be the death of our society as well).

Odds are she’ll be furious with you, which will actually increase your odds to hook up with her the next time you see her out at the bar.

Good luck.

“I am a male in my late 30s and I have been married for close to 10 years, I have two kids and a third on the way. I have noticed that when I do not have sex (which is common now a days) I end up masturbating to help me fall asleep. In your opinion what percentage of the male population does the same?”


Thanks for reading the anonymous mailbag.

As always send your anonymous mailbag questions via email, anonymity guaranteed, at

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.