Anonymous Mailbag

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It’s Tuesday, time for the anonymous mailbag to rescue you from you from your usual doldrums.

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

Okay, here we go:

“I just finished my freshman year in college and in addition to this panic, another challenge I’ve faced is my parents have recently divorced. They still love each other but both are workaholics and just grew apart. They’ve been separated for awhile but just finally decided to divorce legally. My siblings, who are in their lower 20s, and I think it’s for the best because they’ve never been happier. They still talk to each other and get along. With that said, both are seeing other people and there’s a huge age gap. My mom is 48 and seeing a 35 year old. My dad is 55 and seeing a 23 year old. My brother and sister have issues with it. I’m mixed on what to do. They want to confront my parents and say they should see people closer to their own ages. I sometimes agree with it but really feel it’s none of our business. What would you do in my position?”

First, both of your parents may be trying to “win” the divorce. How do you win the divorce in the context you just questioned? By having the youngest, best looking new partner. I’m not sure who started dating the younger person first, but the second person may have started dating a younger person just to get back at the first. In other words, it’s highly possible that instead of trying to find a person to spend the rest of their life with, both of your parents are dating someone right now to provoke the most significant reaction from their former spouse.

I also think there’s a pretty big difference between the ages of who they are dating here. Your mom’s current boyfriend, at thirteen years younger, isn’t that much younger than she is in the grand scheme of things. Put it this way, your dad is 55. If he was dating a 42 year old would anyone think that was particularly notable? I think you may notice your mom’s decision more because it’s less common for women to date men over a decade younger than them than it is men. But her choice in a partner isn’t really that notable.

Your dad, clearly, is dating someone WAY younger than him and most people who saw this couple out to dinner would think it was a dad with his daughter instead of a boyfriend and girlfriend.

Put simply, I can see how a 48 year old and a 35 year old can have quite a bit in common, I can’t see how a 55 year old and a 23 year old can have anything much in common at all.

Having said this, they both just split up with each other after over twenty years of marriage and after raising kids for the past quarter century or so. It may well be that both just want to feel like their lives aren’t over and so they have gravitated towards much younger partners as a validation that they aren’t completely over the hill.

I’m down in Florida right now and my father-in-law pointed out yesterday that his mom felt like her life was over when his dad died in 1980 and she was 67 years old. But then she saw that Ronald Reagan, who she had the same birthday as, was running for president and suddenly felt much younger. If Reagan could run for president, she could still do quite a bit with her own life as well.

And she did, she went on to live to be almost 100 years old. Far from being over, her life still had decades remaining. Seeing someone else her age doing something that had always been the province younger people did made her feel younger.

Your parents may be experiencing a similar feeling by dating someone younger.

It may also be that both feel like dating someone much younger than them is a way to get back into dating life without any of the serious life issues that might arise if they are dating someone their own age. Younger people typically have less complications in their lives. It’s unlike your dad’s 23 year old girlfriend has any kids or is eager to immediately have her own kids, for instance, so both your parents may see dating younger people as a fling.

A big clue on this, I think, is whether both parents are bringing these people they are dating to family events. For instance, let’s pretend we were headed for normal Thanksgiving and Christmas seasons in a few months. Do you believe your dad and mom would bring their boyfriends and girlfriends to family events or would they come alone? What they would do here would give you a big clue as to how much of a serious relationship this is and how much of a fling it is.

Which is why considering all these factors, I wouldn’t say anything to either parent.

Divorces can be emotional and tumultuous times. Both your parents just lost their rock of multiple decades. Considering their kids are all grown now and they don’t have a life partner, they may both be floundering a bit. Having children question their decisions — which deep down they might agree with — could lead to a rift between the children and parents.

Finally, let’s think about this from the 23 year old’s perspective here since she’s the one who is actually in the most socially awkward position. I can kind of figure out what your dad is after here — youth and sex — but what’s she after? Is she simply taking advantage of a sugar daddy’s largess in the short term or is she potentially interested in a life with your dad. My guess would be the former, but that’s a big question too. What are her motivations here?

If you really want to have a conversation about this, I think you could ask your dad, privately, not in front of your brothers and sisters, “Dad, are you interested in having another family or not? Do you want to be 70 years old with a 13 year old kid?”

That’s a fair conversation to have that doesn’t attack him for who he’s dating. My bet is he would say, “Hell, no, I just want a hot girlfriend!”

You may not agree with his position, but it would probably go a long way towards alleviating your concerns about his future life path.

Good luck.

“If a woman is made aware by her OB/GYN that she will very likely have fertility issues in the future, at what point in her relationship with her significant other should that discussion occur? Six months into dating? Before engagement?”

Man, this is a hard question to answer because there isn’t an answer that makes complete sense for everyone.

I think you 100% have to have that conversation before engagement, but I’m not sure there’s an exact month total in the relationship where the conversation has to occur because every relationship progresses at a different speed.

I would say this conversation has to happen whenever either party starts to contemplate that the relationship may lead to a serious life partnership, but it’s hard to know exactly when that is.

This is an especially difficult conversation for women to have because so many women are worried about scaring off a man they’re dating before he’s even interested in a serious relationship at all.

This is also a bit unfair to the woman because many men may have serious fertility issues, but have no clue until they are married and trying to have kids. So they don’t have to discuss it as any part of the relationship. That is, I don’t know of many men who have had their fertility ever checked before marriage. Whereas it’s more likely a woman might be aware of her reproductive health issues long before marriage. So most men never even have to consider this issue.

As a general rule, I think you have to bring up this conversation if you’ve been dating for a while and you begin to have a serious conversation about having children one day. That also seems like a natural pathway to the conversation. Otherwise your partner may remember that conversation and later feel you behaved dishonestly in that discussion.

Because here’s the deal too — and what makes this conversation so difficult — there’s nothing wrong with someone not wanting to sign up, effectively, for adoption. Most people, at least in theory, would like to plan on having their own kids and most people don’t know before they get married if that’s not possible.

Clearly, many couples have serious issues with fertility which can be an immense burden on relationships. But most of those fertility issues aren’t known before the couple are married and attempting to have kids. If you know fertility is going to be an issue, it’s a conversation that needs to occur as soon as the couple is contemplating being together for a long term relationship.

(Additional thought: some women might want to address this issue super early in a relationship because that way a man choosing to break up with them doesn’t feel as much like a personal rejection. I can see a way to have this conversation early on in the relationship, like the first time the couple are having sex. Man: “Are you on birth control?” Woman: “Nope, the doctor told me I have major fertility issues. So you’re in luck, you don’t have to pull out!” Yes, you can kind of make it as a joke, but it may be easier to do it this way for some women then to fall in love with a partner and then have him decide he doesn’t want to be with you as a result. Or to dread having this conversation in the back of your mind because you think it could derail something special.)

Regardless, this is a super difficult situation and my best advice is handle it however you feel the most comfortable. There is no 100% right answer for everyone.

“So I live in Tennessee with my wife and 15 month old son. I have a 9 year old son back in California with my ex. We’ve been separated for 8 years and I’ve been with my wife now for 7 years. Recently my ex found out that her biological father lives down in New Orleans so she is planning a trip at the end of July to meet him for the first time and is bringing my son with her.

My first thought was great I get to drive down and spend some time with my son whose normal routine got derailed by corona, he would have been out here for his summer break so it’s a way for me to see him now.

My wife and mother in law are all about being up to date with corona, watch the news daily and eat up every word they hear. They recently heard that Louisiana is now one of the worst states to visit because of corona. Another thing to note is my wife and mother in law have a strong dislike for my ex because she is a bit of a bipolar witch.

So my question is, me being a 33 year old male who’s decently healthy with no major health concerns, my wife is 28 and much healthier, is there really reason for my wife to be worried about me going down to New Orleans for a weekend, contracting corona and bringing it back to infect all of my family up here? Will there be anything open for my son and I to do? Hotels for me to book a room in? Regardless of things to do I’m willing and eager to go down and risk contracting the virus to hang out with my son but this pandemic and the fact that I have to see my ex is a huge speed bump that my wife can’t seem to get over.”

You’re torn here between two obligations: to your wife and to your son.

I’d pick the son in this situation and let me explain why.

I have three boys right now — ages 12, 9 and 5.

Early on in their lives I traveled a decent amount for work. So I did the typical dad calls via FaceTime and checks in with his kids bit. That’s great — it’s really amazing how we’ve totally accepted and gotten used to the incredible idea that we can call pretty much anyone in the world and see them on our phones — but there still is no substitute for actually being there in person with your kids.

Especially when they are young and their memories are being imprinted in a big way.

Traveling down to New Orleans and visiting your nine year old son for a weekend would be a very memorable experience for him, something that he might well remember for the rest of his life. (Think about how much more vivid many experiences that you had when you were nine are more clear for you than something that you did at 29 or 39. When we’ve had far fewer things happen in our lives, we tend to remember them more clearly).

So I’d go to New Orleans and meet him. As for what to do there, I’d take him an on airboat tour. What nine year old doesn’t like the idea of going to see alligators in a swamp? This is an easy call. Then maybe a ghost tour in the French Quarter, assuming they are going on.

Then let him pick wherever he wants to go eat anywhere in the city. (If he picks McDonald’s, so be it, it’s his choice). At night stream 1980’s movies with him that you grew up liking yourself. Share them together. In my house, for instance, last week we watched all the Jurassic Park movies and my kids loved them.

Furthermore, I’d take it a step further than you are, why can’t you pick your son up in New Orleans and bring him back to stay with you for a couple of weeks in Tennessee? At the end of the visit you can put him on an airplane and send him back to his mom in California. Rather than try to only spend a weekend with him, I’d ask to keep him for a couple of weeks. I’d think your ex would be ecstatic to get a short break from your nine year old, especially in the middle of the coronavirus. But this way you could also, theoretically, limit your exposure to New Orleans, which could keep your wife happy. (Granted you’re bringing a kid into the house, but kids have been show to be very poor spreaders of the disease so far).

As for what to tell your current wife (and, gag, her mom who is also involved in your business) I’d be pretty straightforward — your only obligation isn’t to her. You have a responsibility to be the best dad you can for your first son too. The data reflects that even if you get the coronavirus you — and all your family — would be fine. But you can ensure you and your son socially distance for all the events and activities you undertake with him.

If you really want to bring it home for her, reference your current son. What if she decided to divorce you one day and your son got to see his dad rarely? Wouldn’t she want you to be involved in the son you have with her’s life?

I just don’t see this is as a difficult call, you need to go visit your son. And I’d want him coming back and staying at the house with me as well if I were you.

But at an absolute minimum seeing him in person while you can is a smart move.

When kids are nine years old, they change a ton over six months or a year. If you go that long without seeing your son again he may well write you out of his life. Not out of any particular malice, but just because you haven’t been there for him in any substantial way.

“I own and operate my own business, and have a diverse cultural spectrum of customers. In this new “protest-without-consequences” society we are creating, I’m afraid this will begin to infiltrate my place of business. How should I handle someone who starts to proselytize in my business for or against any of these current hot-button issues (Black Lives Matter/police brutality, pro/anti-Trump, etc), potentially making my employees and other customers uncomfortable? I try to stay as apolitical as possible in the workplace and have explained to my staff to do so as well, as I don’t want to alienate any of my customers on those grounds and thus decrease my revenue.

I know you are a First Amendment absolutist and they are entitled to exercise that right, but you also have said many times that personal politics in the workplace is always bad for business. Aside from snap, emotional judgments in the court of public opinion, what logical recourse do I have if the one expressing their opinions/causing the disruption is a customer?”

I don’t know exactly what your business is, but I don’t see this is a difficult decision, we need less politics in this country, not more.

If your goal is to appeal to all customers, regardless of their politics, I’d tell all my employees to leave their politics, whatever it might be, at the front door of the business.

I firmly believe making everything political is a disaster for this country.

Do we really want, for instance, roofers or mechanics for Trump or Biden? So that you feel like you have to research your roofer and mechanic’s position on every issue before you hire him to fix your house or fix your vehicle.

Do we want Republicans and Democrats to have yellow pages for business, where you insure that you only support people with the same beliefs as you? I think this is just a horrible precedent.

Look, maybe I’m rare in this, but I just don’t care about what my roofer or mechanic or doctor thinks about politics. I want the person who is going to do the best job possible. And if I hired someone to do that job and he argued with me about who I should support for president, regardless of which side he advocated for, I wouldn’t pick that person again.

I do think it’s important to establish that you’re content-neutral on your political restrictions. That is, you aren’t picking sides. You can’t let someone who is pro-choice advertise their position just like you can’t let someone who is pro-gun advertise their position either.

Now, there’s an important caveat here. Some businesses are, by their very nature, political. So if you own a gun store or a gun range, it’s pretty clear you’re pro-second amendment. Or if you run an abortion clinic it’s pretty clear you support abortion rights. But if, for instance, I ran a gun shop I wouldn’t want my employees weighing in on abortion and if I ran the abortion clinic I wouldn’t want my employees weighing in on gun rights issues.

It’s impossible to avoid all politics, but I’d avoid as many of them as possible at my place of business. Especially in 2020.

Good luck.

As always, thanks for reading and send your anonymous mailbag questions to, anonymity guaranteed.

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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