Anonymous Mailbag

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It’s Tuesday, time for the anonymous mailbag! Send your anonymous mailbag questions to, anonymity guaranteed.

As we get rolling this morning, the presenting sponsor of the anonymous mailbag, The Home Loan Expert, has got a great potential prize for you guys — you and 11 buddies can watch the SEC Basketball Tournament with me in a luxury suite in St. Louis. Go register for the contest here and hope to see some of y’all in St. Louis.

Okay, here we go with the anonymous mailbag:

“I am a huge fan of you and your work, and like you and the proud American man I am, share a passion for the 1st amendment and boobs. That being said, I am dating a girl that unfortunately was cursed with very small boobs. Like flat as West Texas. Aside from that, we get along well, she is in great shape with a great figure, and is very smart and we both make very good money. She’s just not rocking a set of chest cannons.

It bothers me more than it should, and I know that I shouldn’t let it defer me from the fact that she’s really great and treats me well. This issue is also fixable with the glorious prospect of plastic surgery, and she would be a stone cold fox with some fake tits.

So my question to you, O wise one, is in two parts: Am I being a completely terrible human being for letting this bother me? Also, she is not self conscious at all about her boob size, so if we continue to date and things look promising, how does one present the idea of maybe upgrading her boobs to a set of knockers?”

I don’t think you can suggest or buy fake boobs for a woman until you are married or, at least, engaged with a wedding date set.

Otherwise you run the risk of becoming guy who buys fake boobs for his girlfriends guy. And eventually that self selects and you end up dating a series of really crappy girls because they know you are guy who will buy fake boobs for his girlfriends guy.

The only thing worse than being that guy is being the guy who attracts those kinds of girls.

Can you imagine dating a guy so he’ll buy you fake boobs? That’s not a girl you want to bring home to mom. If you want boobs that bad earn the money yourself. Or ask your poor dad to buy them for you like any other self respecting college girl would. (I can’t imagine being a dad and cutting a check for my daughter’s fake boobs. Seriously, that has to be the most brutal check any dad ever writes in his life. I think it’s easier to cut a check to get your kid out on parole. Because at least you’re getting your kid out of jail with the parole check. When you buy your daughter boobs you already know how guy’s think and you’re just adding jet fuel to your daughter’s sexual attractiveness. You’re basically just throwing money up in the air and saying, “My daughter looks even better naked. Good luck guys!”)

But back to your question, I think you bring it up only if you actually marry the girl. Maybe, potentially, if you get engaged. But just for a regular relationship that hasn’t led to any sort of life commitment? No way.

You keep silent about your desire for your girlfriend to have bigger boobs until you’ve decided to buy not rent.

Also, and I have no idea why this is, but it seems to me that girls with no boobs frequently have phenomenal asses. It’s like God’s gift to balance out things.

So just enjoy that ass until you get engaged or married.

“Quick question for you. My wife and I are in disagreement on having a 3rd kid. Just for background, we are in our early 30’s and already have a boy and a girl. I’m perfectly happy with this setup, but my wife really wants a 3rd child. She’s the youngest of 3, so she’s always dreamed of having 3 kids.
I’ve got a lot going on with work these days, and I really am not looking forward missing the amount of sleep that comes with having a newborn. There’s also the fact that our youngest is 3, and we are just now getting to be able to do normal activities again.
So I’m really not looking forward to starting all over again.
However, she’s not backing down and trying to make deals. She’s tempting me with a blowjob a night while we are trying. We’ve always gotten pregnant on the 1st month of trying, so I’m not expecting that arrangement to last more than a month. I also don’t expect her to ever let this go, and if I continue to hold out, she may always be mad at me for not allowing her a 3rd kid. Should I continue to say no, hold out for a better deal, or have I already hit the jackpot and should just go with it?”
I think a blow job a night is about as good as you’re going to get.
That’s because I have never heard of a woman who wants another kid and doesn’t get it. I’m sure it happens, every now and then a dad wins these battles, but that’s like a damn unicorn and you have to deal with the fact that you have kept her from having a child for the rest of your life. This seems like the kind of thing that would get brought up all the time, especially if your first two kids both end up fuck ups.
(Related question, is it just me or do highly successful people have a higher share of fuck ups for kids? Is it just because the parents have succeeded that our standard for their kids are much higher or could it have to do with the parents being so focused on themselves and their careers that their kids aren’t given as much attention and time? I’d love to see a study on this. Because I think the fuck up quotient is much higher for the kids of extremely successful people).
Anyway, most women get exactly what they want in marriage because, and you single guys reading this need to pay attention and understand this, being single favors men and being married favors women.
If you’re a single guy you run the world right now. Sex has never been easier or come with less strings attached. You have abundant options and virtually no obligations. Putting it in tennis terms, you’re up two sets to none and the woman has no shot at returning your serve in the third set.
The match is yours unless you really screw it up.
But the minute you get married the advantage shifts back to women. They’re serving for the match on you all the time and the ace serves just go whizzing by you — new furniture, home she wants, you never drive a new car for the rest of your life, Saturday nights at Costco, babies, private school, — boom, boom, boom, most of the time you don’t even get the racket off your shoulder.
You are, at best, the appendix of your family, a totally vestigial organ.
That’s why you should just go ahead and accept that you’re going to have a third kid. Women get what women want once you get married. That’s just how the game is played.
Our third kid is awesome. I can’t imagine not having him and I suspect that’s how most families feel about their third kids.
So sleep now while you can can enjoy the blow jobs.
Plus, when you know you aren’t having any more kids — and I’m guessing you guys won’t be — there’s some fun with having a third kid because you know you’re doing everything for the last time. I feel like the first and second kids can be a total frenzy, but by the third kid you’re much more chilled out. You’re not afraid of every little thing and I think that tends to make the third kid easier to raise. They’re more chill because you’re more chill.

“As the flu epidemic is sweeping through this country, it inevitably took my wife down for a few days a couple weeks ago. We quarantined her in the back room so as not to infect our two little boys or myself.

Anyways after she recovered, I was out with a group of 8 guys (7 of 8 married) at a sports bar hanging out.  At some point one of the guys asks the group “Hey if your wife gets sick with flu and you come home and she’s naked in the bed and says I want to have sex, how many of you guys risk the flu to have sex with your wife?”

Of course all 8 guys raise their hands yes they would do it.

A couple days later we are hanging out with a group of 3 couples and one of the guys brings up this story and all the wives call complete bs, there’s no way all the guys would risk the flu for sex.  My wife said at best it’s maybe 40-50%.

What say you Clay?  I think it’s at worst 85-90% yes for a heterosexual guy with a working penis risks the flu for sex.  I personally am not in the business of turning down one of the few opportunities I get for sex with my wife no matter her health condition. Am I way off?”

See, I’m a total germaphobe so there’s no way I’m doing this.

For a cold, maybe, for the flu, no way.

In fact, right now I’m terrified my kids — or my wife or me — are going to get sick between now and Friday when we leave for a Star Wars Disney family cruise. (Yes, we’re really doing this. They have Star Wars characters on the cruise ship with us for the entire week. This is the equivalent of an orgy at the Kappa Kappa Gamma house for my boys. They literally can’t think of anything better existing than this.)

But I’m terrified that one of us will get the flu, which means, if you’re anything like my family, that everybody will get the flu, and then we’ll all end up sick on the cruise.

So this question hit me at the absolute worst time. It’s like someone making a joke about HIV the week after you slept with that hooker and a condom broke.

Plus, I absolutely despise the flu.

So there’s a 0% chance I’m having sex with a flu-addled wife.

Now if I were single and it was a girl that I hadn’t had sex with before and she texted me to come over that she had the flu, but she wanted to have sex with me, I’d be there in like five minutes.

“My wife and I just got pregnant with our first child. We are excited but are in a spat over when to tell people. Generally it sounds like the 12 week mark is the right time. Is there a hierarchy that exists for this, or should all of our immediate family, extended family, friends, and coworkers all be told within the same 24-72 hour period?
My wife wanted to tell her sister the day after she peed on the stick and for 2 pink lines. I put the kibosh on that and said it is our secret until we tell everyone at the same time.”
I don’t think you tell everyone at the same time, but I think you need to wait until after the first trimester to tell people. Otherwise you could have a miscarriage — which is insanely common — and then you have to tell everyone about your miscarriage, which is awful.
Having said that, I think you tell everyone privately and tell them you’re just telling them, but that they can’t tell anyone else. You do this for two reasons:
1. It makes them feel special and you get to share the joy of your first kid with each of them individually.
2. You find out who can keep a secret.
For instance, I knew our first child was going to be a boy and I was the only person who knew this for months. Only my wife knew I knew and I lied and told everyone else I didn’t know the sex either so they wouldn’t badger me to tell them. (But I did know and I kept the secret perfectly and no one had any clue I knew. And even my wife didn’t find out the sex in advance because I kept the secret perfectly. This means I could head up the CIA, the NSA, or the FBI.) So, not to brag, because I’m not the kind of guy who likes to brag on himself, but I’m great at keeping secrets, maybe even the greatest secret keeper ever. (Or maybe second only to David Stern who has so far kept the secret that he suspended Michael Jordan for gambling on basketball for two decades).
Having said all of this, your wife is totally going to tell her sister and not tell you that she told her sister.
And I think that you probably just have to deal with this.
“How do I ask Britt McHenry on a date without appearing creepy? We live in the same city and work in conservative media.”
I can’t speak for Britt in particular — although I do love that this is the first time anyone has asked about a specific girl I know in the media in the anonymous mailbag so Britt should be honored — but the key to dating attractive women is two things:
1. nonthreatening access
2. confidence
The first is important because attractive women are constantly being hit on. It’s hard to pull off a date if she doesn’t know you at all in the first place. And it’s hard to stand out as worthy dating material just hitting on someone randomly at a bar unless you’re particularly good looking. So if you can meet an attractive woman in a way that sex isn’t your obvious goal — at work, at school, through friends in a social setting — you get the time to impress them with your wit, charm and personality — three things that women care about — without it being obvious that you’re trying to sleep with them. (If you’re incredibly good looking, amazingly athletic or insanely rich then you can also get access to tons of good looking women without needing access in advance, but those are rare attributes generally speaking. Most guys are relatively average in athletics, looks, and wealth so nonthreatening access becomes important).
The second most important attribute is confidence.
You have to believe in yourself. And I don’t mean fake, readily apparent I’ve got big muscles and work out in front of the gym mirror all day bravado that actually crumbles in real life, I mean actual self confidence that resides deep within your core. Every woman’s biggest fear is that the guy she’s dating or married is a total loser, every man’s biggest fear is that the woman he is dating or married is psycho.
Having confidence in yourself is the best possible male aphrodisiac. And you ultimately can’t fake it. Or at least you can’t fake it very long. Women will eventually detect whether you have confidence or you don’t. And they certainly will smell out insane overconfidence that isn’t supported by any tangible skills or work ethic so that doesn’t work either.
And if you don’t have self confidence now, how do you get it? Partly I suspect it’s innate, but confidence can also be learned. How? Find something you’re good at and work at getting better and better at it. Having a talent is sexy, whether it’s playing a guitar or selling homes. Eventually turn this talent into a career if you can. The more success you have in your career — and the harder you work at refining your talent — the more self confidence you’ll have.
And if you have confidence in yourself and you can meet women in a non-threatening environment you’ll be well on your way to outkicking your coverage.
Good luck.
Send your anonymous mailbag questions to

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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