Anonymous Mailbag

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It’s Tuesday and I hope you’re all back to work by now so I can help rescue you from work doldrums with anonymous mailbag questions.

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

Here we go:

“I am a 42 year old man who has been married for 20 years. My wife is the same age. We have no kids. Our marriage has been good and we have an above average sex life. I love my wife. With that said though I started having an affair about 3 years ago. I met her at a college football game. She was a 20 year old student at the time and is now 23 and working. We were spending the night together about twice a week before and pandemic. My wife normally traveled during the week. Since the pandemic we have had to get creative sneaking around during the day. I have fallen in love with this younger woman. The sex is great. I’m debating whether to leave my wife for her. This other woman has wanted me to for about a year. I’m wondering if I’m having a mid life crisis. Would you have any advice or things to consider for my situation?”

Okay, let’s start here — you’ve been married for twenty years and say you love your wife. But you also now say you love your 23 year old mistress and that you’re considering leaving your wife for her.

Then you say you’re wondering if you’re having a mid-life crisis.

So let’s unpack this. I think “mid-life crises” are typically just people reaching middle age and realizing their life hasn’t necessarily gone the way they’d hoped it would go. As they reach forty years old — or the vicinity — many people sit around and wonder whether this is their last chance to make the life they wished they’d had a reality.

That’s why my first question for you is this: what do you not have in your life now that you wished you had? And how is this younger woman going to make that a reality in a way your current wife can’t? I can’t answer these questions for you, but the first thing that comes to mind is do you wish you’d had children? You and your wife have been together for twenty years and have no kids. Was that your choice, her choice, or a mutual decision? If you have reached forty years old and suddenly realized you’d like to have kids, then, assuming your own wife doesn’t want them, that could be a rational decision to switch partners.

But, again, that’s a rational choice you’d be making based on something you want in your life that you don’t presently have, which is why I think it certainly wouldn’t be a mid-life crisis. To me a “mid-life crisis” denotes irrational choices made that aren’t in your best interests. Deciding to do something that you now know you want isn’t a mid-life crisis, it’s just making a decision to change the trajectory of your life.

I think what being middle aged, or older, frees you up to do is to stop pretending you care about things you don’t. As you age you should be less concerned about what other people think about you. It’s kind of like getting a ton of money. Lots of people say money changes people, but I don’t think that’s true, I think money just makes you more of what you already were. Money is an eraser, it gives you an opportunity to live as you would have lived without constraints. People who are already assholes become bigger assholes when they are rich, people who are giving become greater givers when they are rich. Money simply allows your true self to be revealed.

And I think age does something similar.

The second big question I think you need to answer is this, will you actually be happy with the younger woman? Because when the mistress becomes the wife that opens up a new spot for the mistress. What makes you think you’re not going to end up in the same place you already were with the new girl? And, importantly, does the new girl actually want to marry you? She may be more attracted to you right now because you’re not all hers. She might also be competitive with your wife. But once you make the decision to commit to her full time what happens to her attraction level?

It’s possible she’s going to be way less interested in you once the struggle to control you is over. In other words, the chase is way more compelling, often times, than the catch. You’re thinking about this entirely from your own perspective, but you have to remember that any marriage is not a one person show, you need to be thinking about your partner long range here.

You’re going to get married to someone who broke up the marriage of someone twenty years older than them. That’s not exactly a moral strength. If she was willing to break up your marriage, how committed would she be to the two of you’s own marriage?

But ultimately the biggest question is what do you want your life to be? Do you want to start all over again or do you want to stay with the woman who you’ve been with for a generation? You’ve already made the decision to be unfaithful to your wife — and you didn’t just cheat, you fell in love with someone else — so what’s your plan going forward now? I feel bad for your wife, who presumably has no idea what’s going on, and I think if you decide to stay with her you need to consider being honest with her so she has the same choice you did, does she want to stay in this relationship for not?

In general, I’m skeptical that you’re going to leap into a relationship with someone twenty years younger than you and everything is going to be perfect for the rest of your life. I’m sure that happens sometimes, but I’m not sure it’s likely to be happily ever after for the two of you.

I certainly understand why casual sex with a college girl is enticing for a forty year old guy and might spice up your life, but there’s a big difference between casual sex and a real life spent together. The key here is you figuring out what you want from the rest of your life.

And ultimately no one else can answer that question for you.

“I am the Best Man in my brother’s wedding which should have been two weeks ago. Back in April, he and my future SIL made the decision to push the wedding back to September in order to allow for grandparents to feel more comfortable attending a 100+ person event.

My brother and I attended college together so we generally have the same group of friends. One of our best friends from college was supposed to be a part of the wedding party. His wife is due with their first child at the end of July so when the wedding got moved it was understood that her attending would probably not happen but we assumed my friend would be in the clear. They live about two hours from the wedding venue so traveling would not require getting on a plane. Our friend’s wife and my brother have a bit of a history. We all attended college together and they dated during spring semester freshmen year. Things did not end well and she has held a grudge against him ever since even though this was many years ago. Our friend doesn’t give a shit they dated and my brother was actually in their wedding which I have heard caused some arguments for the couple. A few days ago, out of nowhere, our friend said he could no longer attend the wedding because his wife said it was “unsafe to attend a large event during covid and then come home to a baby”. This news spread pretty quickly among our friend group. There was another couple (live locally so no travel required) invited who are due about the same time and, when they heard the news, the wife got super paranoid and is now wondering if skipping the wedding is the right and safe call.

My brother is pretty upset by all of this but is very non-confrontational and won’t say anything right now to our friends. He used to have an anger issue that got him into quite a few physical altercations in college (he was THAT guy consistently getting kicked out of places for fighting) and I think has become too non-confrontational as a result. I want to help but I have no idea what I should do. As the Best Man, should I call out our friends for backing out on the wedding (particularly one of the groomsmen)? I think it’s perfectly fine for them to attend but I get they might be a little nervous as parents and that has me a little conflicted. How would you handle this?”

I’d stay out of it.

I’m sure your brother’s friend feels awful about not being able to attend the wedding, but he’s having his first kid and his wife, who may well be motivated by not liking your brother that much, is choosing to use the coronavirus as an excuse for why he can’t attend the wedding.

Personally, I happen to think that’s an exaggerated response given the data about babies and the virus. But I’m sure there are many people reading this right now who would disagree with me. In other words, this isn’t a totally irrational decision made by the new parents.

And the point is pretty clear — it’s not your decision. Whatever arguments you could make about why he should be coming to the wedding are unlikely to change the new mom’s opinions. And just think about what this poor bastard’s life would be like if he goes to the wedding and in three days the baby gets a cold.

She might murder him.

This couple was willing to come in April, but they can’t come in September, which is pretty much the opposite for the grandparents. So you gained some people and lost some people as a result of the data change. Personally, I think the grandparents being able to attend is a far bigger addition than the loss from the groomsman. In other words, if you’d had to decide who should be there back in April isn’t this a wedding trade you would have made?

I’d also say this, a 100 person wedding in September seems pretty aggressive. Would the wedding really be that much worse if it were smaller? I think the party atmosphere isn’t going to exist for most weddings for a while. And it’s certainly not going to be back to normal by September.

The coronavirus has upset a huge amount of plans for hundreds of millions of people all over the country. The decision to change many of those plans has been rational, but many of those decisions have also been irrational. But that’s the thing about people, you only really get to make your own decisions, you can’t make other people comport to your decisions.

The odds of you being able to change your friend’s wife’s mind are virtually zero. So all you’d do is make a relatively small issue a much bigger one. This guy’s not the priest or the best man or a close family member. He’s a groomsman. The wedding will go on fine without him.

I’d advise moving on and not talking or worrying about it going forward. Instead of focusing on the people who aren’t coming, I’d focus on the ones who are.

“My six friends and I booked a trip to Miami back when Florida became one of the first states to start reopenings. We figured at that point, which was back in May, that by the middle of July, a lot would be reopened (maybe not everything, but enough to have a good time in a fun vacation spot).

We’ve seen the cases in Florida and in Miami rising the past week and all the doom and gloom media coverage surrounding it. Just today, the Mayor of Miami mandated that masks have to be worn outside in all public places, as well as inside. I’m not exactly sure how much or how well that will actually be enforced at beaches or restaurants, but it’s still a trend in the wrong direction regarding the outlook of our trip.

So, my question is, on a scale of 1 to 10, how worried do you think we should be that in the next month before we get there, that beaches and whatever businesses that have opened would actually be shut back down again, and that the city, or even the entire state for that matter, would go back into a full blown stay-at-home order? I find it hard to believe that Miami could be the first city in the whole country to do that big of a 180, but at this point, no possibility can be ignored.”

I’m going back down to Florida on Sunday for a week with my family.

I spent most of the month of May in the state and know things are back to pretty much normalcy there. But I’ve been staying on the beaches up in the Florida panhandle as opposed to South Florida. So I can’t speak to what things are like there right now.

But I think the odds of the city shutting down for tourists again are low.

Having said that, Miami in a pandemic is not the Miami that you’re used to visiting. I’m not sure what you’ve done for hotels, but I’d plan on a relaxing trip, not a partying trip. You can hang out at the pool and at the beach, but I don’t think the night life scene will be very pronounced. And I certainly don’t think the South Beach club scene, if that’s what you’re looking for, will be wild at all.

If you haven’t already booked a hotel, I’d even consider booking a resort with a great pool and just turning it into a resort style vacation — where you golf, eat at a few nice restaurants, and hang out by the pool with your friends — as opposed to a bacchanal.

I’ve gotten asked a ton about summer vacations this year and to me this is a summer to pick a destination you can drive to as opposed to trying to plan a trip that involves airfare or substantial distances to travel. I love to travel with my family — and we’ve flown on planes once down to the beach already — but this summer we are going south to Florida and north to Michigan, both in cars.

I looked into taking flights to other parts of the country for vacation, but there is a substantially reduced number of flights and given the reduced seats on those reduced flights they’re almost impossible to book right now. So we’re taking it easy and will take a big vacation next year.

“I’m a single female who will be 40 in December. I’ve been married before and have two girls who are 10 and 17. I’ve been single for about 9 years.

I’ve dated off and on throughout the past decade. Lots of bad online dates. Some recurring booty calls. Nothing has really worked out.

I have a friend that I dated for several months last year. We can talk for hours. We have a lot in common. We love each other, but I love him as a friend and he loves me to the point that he’s mentioned marriage.

Here’s my issue: the physical chemistry is way off. I’m not ashamed to admit that I’d like to have sex at least once a day, if not more. I’m very touchy even when I’m not in the bedroom. He doesn’t hold hands. He doesn’t like kissing. The sex that we’ve had can best be described as “meh”. He will seriously just lay back and let me do the work and not make a single noise. It’s boring. I’ve tried to get him to open up in the bedroom but he’s about as vanilla as they come. It seems strange that I’m trying to convince a man to have crazier sex more often.

This lack of sexual chemistry is what caused me to end the romantic part of our relationship and stay friends. However, I’ve recently been wondering if I’m being unreasonable. Here’s a man who works hard, respects me, likes my kids and family, and makes me happy. But the other part of me wonders if I could be with someone who can’t meet my physical needs.

Is it settling if I decide to date him again? Am I being unrealistic to think that I can have the great guy and the great sex life? Am I getting too old to keep viewing sex as a deal-breaker in a relationship, when so many people say it goes away anyway? I have no idea what to do. I can’t picture not having him in my life, but I also can’t picture having silent sex a few times a week for the rest of my life.”

You’re in the interesting position of being able to say this sentence to a man, “I want to seriously date you, but you’re going to have to screw me more often and in more creative ways.”

And maybe it’s just me, but I can’t imagine a heterosexual man hearing this sentence and being like, “Sorry, I can’t make that happen.”

So I feel like you can work with him here.

Ultimately though this question is similar to the question we had from the married guy to start off the anonymous mailbag, it’s what do you want with the rest of your life?

You’ve been single for nine years. Let’s pretend this isn’t the guy for you. Would you be okay being single for the rest of your life if a better guy doesn’t arrive? It’s not like you’re alone, you’ve got two daughters. Granted one of them will be an adult soon, but your ten year old daughter is still eight years away from college.

That’s your window, to me, right now. You need to find out what you’d like over the next eight years. Because once she goes off to college then you’re suddenly going to find yourself with a ton of free time and can pretty much do whatever you want.

I’ve been a dad for 12 years now and every now and then my kids are all out of the house and I have no idea what to do with myself at night. It’s just so quiet and there’s this yawning amount of space to fill. I can’t even imagine what my life would be like with all three boys out of the house right now.

What do you single people without multiple young kids do to fill up all the time? I’m seriously baffled. Which brings me back to the comment I made years ago, until you have kids you aren’t busy. Trust me, you aren’t. You might think you are, but you really aren’t. Even if you’re working 14 hour days you still have ten hours a day where you have no one to be responsible for but yourself. So if you’re young and you are reading this right now you ought to be working your ass off.

Back to your question, in theory, my kids will all be out of the house in 12 years.

That sounds like a long time, but then I flash back and realize how fast the 12 years I’ve been a dad has gone and it’s wild to me to think that at 53 years old I’ll have three adult sons living outside the house. Then what? I mean, I know my kids will still need me for things, but my day-to-day parenting responsibilities will be minimal.

Anyway, I’m clearly projecting now, but I’m confident I’ll be happy with my wife then. I’m not sure what we’ll do without kids to parent all day long, but we’ll have to cross that bridge together.

That childless day is coming sooner for you than it is for me.

So what do you want when your daughters are both grown? That’s the destination you need to be building towards.

I don’t see why you can’t try to turn your current boyfriend into a sex-driven maniac in the meantime. Unless he’s gay, I don’t see how a heterosexual man can’t get pulled into having more sex.

And if it doesn’t work out, you can keep your options open elsewhere and see if anyone better shows up in the next eight years.

If they don’t, then once your daughter leaves for college your life really will open up. You just have to decide what you want and what you’re willing to risk to get there. Do you want perfection, or do you want real life?

Good luck.

As always thanks for reading the anonymous mailbag. 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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