Anonymous Mailbag

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It’s Tuesday, time for the anonymous mailbag to solve all your life’s problems.

Right off the top up here, I want to let you know that the “Wins and Losses” podcast is back up and running and we’ve got two brand new long form conversations that I think you guys will love: Auburn basketball coach Bruce Pearl and Seth Dillon, who runs the Babylon Bee. If you haven’t checked out these long form conversations yet, I think you’ll enjoy them. There are 45 of them now of a variety of subjects and persuasions that I’d encourage you to check out.

As always, send your anonymous mailbag questions to, anonymity guaranteed. Keep loading up the questions and I’ll keep firing away with the responses every Tuesday. But, as always, the anonymous mailbag is only as good as the questions you guys send in.

With that in mind, here we go:

“The city that my brother and I live in was one of the hosts of the first round of the NCAA tournament. We decided it would be fun to surprise our kids, pull them out of school, and take them to see a full day of hoops. I have 12 year old twins (boy and girl) and my brother has two boys (ages 11 and 7). Throughout the drive to the arena and first session of games my usually talkative seven year old nephew was super quiet.

We went out to dinner in between games and, in the middle of it, he just bursts out the following question “Dad, why does (insert classmates name) have two moms instead of a mom and dad?”

The older kids all broke out hysterically laughing as my brother and I tried our best not to laugh. My brother spent a few moments thinking about how to answer and finally settled on “well sometimes two mommies love each other instead of a daddy and mommy” (admittedly not the best answer but I don’t know how he should have responded there in the moment). My son followed up his answer with a “yeah duh they’re called lesbians and they’re hot!”

I should have kept it cool but that comment combined with the look of disgust my daughter gave my son caused me to legit spit my drink out in laughter. Easily one of the funniest things I have seen one of my kids say. My brother quickly changed the convo and I thought that was the last of it.

That turned out to not be the case because my daughter eventually said something about it to my wife. Now my wife is telling me I need to have a conversation with my son about it and wants me to find out what drove that comment aka is he watching porn or did he pick it up from the older kids he plays basketball with? I have no idea how I am even supposed to approach this with him in a non-awkward way.

With how easily accessible it is nowadays, it would not surprise me if he has seen porn. However, he also just spent the last four months playing basketball with kids two years older than him and I’ve noticed he has picked up some things from them in what seems to be an attempt to “be cool” and show off.

How should I go about having this conversation with my son? Brushing it under the rug is not something I can do because my wife keeps hounding me about it. Also, as he is approaching his teenage years, how should the topic of porn be treated? I know he’ll come across it eventually (if he hasn’t already) and if it happens when he’s older and mature enough then that’s fine. However, he is still years away from that being the case but trying to “protect” him from it almost seems futile because it’s so easily accessible now and let’s be honest our kids can easily outsmart us technologically anyways if we try to stop their access.”

If I were you, I’d be so tempted to sit my 12 year old son down, bring up the conversation at dinner and his comments about lesbians and then say, “Just so you know, sometimes lesbians aren’t that hot, bud. What you need to focus your attention on in the years ahead isn’t lesbians, they don’t like boys, you need to focus on the hot bi-curious girls. Those girls are loads of fun.”

And then give him a fist pound and a “we good?” and immediately report to your wife that you’d had the lesbian conversation with him and all was well because he was just repeating a joke he’d heard from the older boys. (Which is what most likely happened). That puts the onus on her to follow up and see what kind of conversation you had about lesbians with your 12 year old and my bet is she won’t ever ask him about it. Boom, you’re home free!

Obviously I’m kidding here, kind of.

The biggest issue, which you are avoiding, seems to be your narc of a daughter. You’ve got to tell your son to watch out for his twin sister, one day it’s a joke he tells that gets repeated to mom, and then this easily leads to her narcing on him for skinny dipping in the local lake with other young girls of questionable morals, aka potentially, and hopefully, hot bi-curious girls.

Again, kidding.

Kind of.

In all seriousness, you’re facing an issue all parents face in the present age. When boys around my age were growing up, we had to work to see naked women. Getting a magazine with naked women in it was the holy grail. Nowadays there is porn everywhere. It’s almost difficult not to see it.

Kids are often seeing porn before they are even old enough to have much, if any, interest in sex at all. So how do you address this omni-present pornography with your kids, particularly when, as you said, they are smart enough to outsmart any of the filters you set up online to keep them from seeing it?

That’s a huge challenge for parents everywhere.

I think your son’s joke is fine and it’s a joke that made Howard Stern a billionaire so it has some universal appeal for men, young and old. But asking him where the joke came from is a conversation you should probably have with him. (Not in front of his sister or his mom, which might make him feel awkward.) Just a good ole fashioned “man-to-man” conversation about lesbians.

My bet, as I stated above, is this is a joke he picked up from the older boys.

You can let him know that as he gets older he may hear jokes from boys — or even see things they share with him — about sex. And that you will be there to have those discussions with him. I think it’s probably worthwhile for you to even have a rudimentary sex conversation with your son while you’re asking him about this joke since he is, after all, 12 years old and hanging out with 14 year old’s. That’s a big two years, those boys may have scraggly mustaches now. And if they have scraggly mustaches, they are definitely looking at porn.

Again, much like my own my seven year old, who has two older brothers constantly teaching him jokes above his own age level, I think your son probably got this joke from his older friends. To wit, a couple of months ago my wife was trying to reach a vintage Scottie Pippen jersey on the top rack of a sporting goods store, but she wasn’t tall enough. So she said, “I could really use a big pole right now.”

And my first grader, without skipping a beat, immediately replied, “That’s what she said.”

My wife doubled over with laughter over how perfect his delivery was. He’s in first grade!

Asked how he knew the joke, he said his brothers had explained “The Office” Michael Scott joke to him.

In your conversations, I’d probably also go ahead and mention porn, especially if he’s hanging out with older boys. The 14 year old boys have definitely found porn. What I’d tell him is it’s perfectly normal to be curious about sex, but that most of the porn he may see won’t be representative of how most people have sex. And that, again, he should ask you about any questions he might have going forward.

Final thought, it’s also worth noting that your daughter, who is also of adolescent age, was in a bit of an awkward spot for this lesbian conversation given that she’s the only girl in a group of five men and boys attending a basketball game. Maybe that also partially explains her reaction and it’s probably worth having a conversation with your son about how his teenage sister, even though they are the exact same age, is likely going to experience adolescence much different than he is.

And that he should be aware of that and her feelings when he’s hanging out with her and their friends.

Good luck.

“My wife is in her 40s and unfortunately, she has early onset dementia. She’s basically the girl from 50 first dates only she doesn’t drive or have access to money. She seems happy (lack of responsibility?) and I’ll never let her want for anything.

Now the moral conundrum. . . I’m still attractive, fit, and in the demographic where I could cast a wide net. Hell, I think a third of the women out there would be into my no strings attached situation.

The other part of me says, “in sickness and in health.” I should just sacrifice that part of my life and accept that this is where I am. I can always put that energy into working out and burn off the steam.”

I’m not a medical expert here, but what is your wife’s prognosis? That is, how rapidly is she deteriorating and what kind of future is likely for the two of you? Are you going to have home health aides helping to take care of her in the near future or is this something that will last for decades, potentially?

I think that matters in terms of your decision about what to do with your life.

Also whether you have kids matters a great deal as well. It doesn’t sound like the two of you have kids, but I think that would be a huge factor. You definitely can’t start dating other women if you have kids who would see this happening.

I don’t know what kind of community you live in, but if you start squiring around other women eventually your friends and family are going to find out. It’s not easy for a fortysomething guy to suddenly start dating again without others knowing. Plus, I think you owe it to the girls you’re dating to explain, at least in some measure, your situation.

I think you are way overrating the number of women who would find your situation to be ideal. I think most of them would be uncomfortable to get involved in any way here. You’re not single and 25 or divorced and forty, you’re married with a severely ill wife. Your wife’s health is a big part of your life. And it seems like it would be pretty stressful, at least to most people. Even if you’re in casual relationships with other women, it would be impossible not to address this issue with them.

I mean, could they even visit your home?

Finally, pretend you were in your wife’s situation, what if you were the one with dementia and she suddenly starting dating again? You might not know it yourself, but it would still be pretty disrespectful of your relationship. And others would see it and think that reflected poorly on her.

The same thing will happen with you.

Without knowing all the specifics of your wife’s health situation and its timeline, the fact remains: you aren’t single. Presumably you aren’t going to divorce her. So your marital status isn’t going to change, potentially for some time.

If in the years ahead it becomes necessary for her to live in a home to receive care, I think you can begin to consider the dating process then, but the idea of you hopping on a dating site and just running through random girls because your wife has dementia feels, honestly, kind of awful.

Eventually you’d have to be honest with these women you’re dating and I can’t imagine they will receive this news very well. And the women you’d attract who wouldn’t mind this, at least early on, would be pretty awful too, I’d think.

Now if you happen to meet a woman while living your life normally and eventually enter into a relationship, I think that’s different, but actively seeking out someone to date while your wife has dementia seems pretty difficult to explain to most people.

But this is a situation, honestly, that most people don’t confront so I’d encourage you to seek out support groups for others in situations like yours. I think that would help you a great deal.

Good luck.

“My girlfriend and I are incredibly happy with one another, and are currently set to move in with one another this month, and I’ve honestly never been in a happier healthier relationship.

However, we have one issue that I need advice on. I’m 25, and my girlfriend is 36. We have 0 issues when it comes to age, and our families and friends have all blended together and no one questions our age difference whatsoever.

The question of kids has come up though and I’m concerned moving forward. I’m a big believer in the Clay Travis theory of having kids as late as possible, and between her and I, we make a decent combined living (enough to support one child without altering our current lifestyle at all), and I’m finishing up graduate school in the fall and already have 4+ years of experience in my field so I think financially would be fine.

What’s my play here? I love her and no question want to have kids with her, I just wish we didn’t have to fight that time clock. Any pregnancy after 40 is considered a major risk.

Some advice from you would be great. I know you’re against guys my age having kids but also reading you talk about your family and kids has been inspiring in some ways, so I figured you’d be good to ask.”

I’m in favor of men waiting to get married and have kids because I think most men are better dads in their forties than they are in their twenties and thirties.

But that’s a general proposition, not an exclusive one.

If you truly love this woman who is 36 and want to have children with her, you don’t have the luxury of waiting a long time for children.

Women’s biological realities are different than men’s. She needs to have children sooner rather than later. Especially if you want to have multiple kids.

In my ideal world every man would get married in his thirties and he’d marry a woman four or five years younger than him. Because that’s probably a rough maturity equivalency. Then you could be married for several years before you needed to have kids.

But that’s a generalized and idealized world. Not every relationship fits those parameters. In fact, most don’t. If you’re sure that you want to marry someone and you’re sure you want to have kids, you have to bend the idealized world to your reality.

Get married and have kids sooner rather than later.

“A guy from high school invited me and someone else we graduated with to his house to watch (redacted sporting event.) We graduated 10 years ago and weren’t super close, but I appreciated the gesture. I am much closer with my fellow invitee, so after seeing his acceptance, I accepted the invitation. A day later, my buddy backs out, leaving just me and the host. Neither of us want to go through with this encounter, but he’s too nice to rescind the invitation. How do I get out of this? I don’t have a wife or kids to blame it on. Do I just go and sit in awkward silence?”

This is easy, you just text him and say since it’s just the two of you, why don’t you go to a sports bar to watch the event? If he says yes to that then you reach out to a couple of other people and see if they’ll meet you there. If he says no to the sports bar then he’s made the choice not to hang out with you.

I also think you could easily call him and explain that since the situation has changed you are going to bail on hanging out with him too. You can then get on a text chain with the other friend and pick a new time to hang out together.

Unless you’re good friends with someone, a man date to watch a sporting event with just the two of you sitting alone together in his house is super awkward.

So pick either of the options above and you’ll be in a good spot.

As always, thanks for reading the anonymous mailbag. Send your questions, anonymity always guaranteed, 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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