Anonymous Mailbag

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It’s Tuesday, which means it’s time for the anonymous mailbag.

But here’s the deal right off up at the top — the questions of late are not very good. It’s possible that’s because I have solved every question in the Outkick universe over the past five years. And that there’s just nothing left out there.

If that’s true, which it may well be, I’m fine with shuttering the anonymous mailbag for a while and bringing it back sporadically as the questions become better.

But that’s not my choice, it’s your choice.

So if you or your friends have great anonymous mailbag questions, send them to, otherwise we’re going to have to take some time off to allow better questions to pile up.

With that statement ringing in your ears, here we go:

“I’m 35 and I recently started seeing a 40 year old. We met online and have been dating for almost a week. We ended up sleeping together on the first date and we’ve seen each other almost every day since we met. We stay at each others place and have sex before bed and have morning sex every day.

One night she had dinner with a friend and asked me to come over when she got done with dinner. I didn’t know until I got there that she was hammered drunk. I helped her get undressed for bed and she asked if I loved her. This was the third day of us knowing each other. I didn’t think anything about it at the time because she was drunk. The next evening she was having a few drinks with a friend and invited me to the friends house. My girlfriend wasn’t drunk but the friend was sloppy drunk. The friend pulled me aside and started asking me about how I felt about my girlfriend and if this was the real deal or not. I told her we’ve only known each other for a few days but I like spending time with her. Then the friend talks privately to my girlfriend telling her that I’m not that into her because I can’t answer her question.

We leave and joke about how ridiculous the friend was on our way home. That night as we were having sex my girlfriend said something that sounded like, “I love you.” I replied, “What did you say?” She waited a moment then said, “You feel really good.”

I felt like this was way too soon for all of the “I love you” chat, so I ended the relationship. I’ve been debating about trying to get back together with her but I’m not sure what to do. She’s great in bed. Am I crazy?”

I don’t think you’re crazy, but I think the forty year old girl you’re dating has major issues. And I think you have to seriously consider whether you want to be a part of her issues going forward.

Based on your email I don’t know what her background is, but I suspect she has had bad relationships in the past and has tremendous issues with insecurity and is also simultaneously desperate to be loved. That’s a tough combination.

Her profession about loving you, in other words, isn’t about loving you at all, it’s about wanting so desperately to be loved that she wants you to respond that you love her too.

It’s a cliche, but in order to truly love someone, you have to first love yourself. I doubt very seriously whether this woman loves herself which is why she so desperately wants you to love her.

If this girl were 19 or 20, I’d simply say she’s got maturing to do and one day will be fine. But she’s not, she’s forty. You didn’t give me any background on this forty year old woman, but I’d be curious to know if she’s ever been married before. I’d bet she has, perhaps at a young age, and it ended very badly. As a result, she may be emotionally stunted based on how that relationship went.

Either way, something in her past is a major issue. And that’s going to keep rearing its head for you if you stay in a relationship with her. I’ve said this before, and I think you have to get older to really understand it, but someone else doesn’t make you happy. You make yourself happy. Now you can share your happiness with someone else and the two of you can grow together and make each other even happier than before, but someone else can’t make you happy.

And someone else can’t make you love yourself.

This woman sounds like she believes both of these things can happen through the man she’s dating. But as great as you may be, there’s no way a woman of this age should be saying she loves you this quickly. I would bet that you’re not the first person this woman has behaved this way with before either and it’s probably why she’s still single.

She has issues. And they seem like they are fairly significant.

The question you have to answer is this: do you want to help fix those issues with her or not? If you do, call her again. But if you’re just looking for sex, is it really that hard to find sex as a 35 year old single guy?

I’d bet not.

So make your choice.

“I have two daughters, ages 8 & 6. They are starting softball and T-ball this spring. My wife and I have been encouraging our girls to try various sports, along with their regular dance and gymnastics, to see what they enjoy and to give them opportunities to exercise social skills, learn the importance of team dynamics and build their confidence.

I’ve been in the military for almost 16 years and because of my current assignment I have to travel fairly regularly. I played multiple sports in high school and college baseball at the D2 level, I love sports and recognize the impact it had on my life and in preparing me for my current career. Under other circumstances I would absolutely help coach their teams, especially in softball.

Last night my eight year old had her first team meeting/practice. It turns out that her coaches are a transgender man (female to male), his wife, and a third male that lives with them and may or may not have had a previous relationship with the couple (it is possible he is the biological father to one of their children who is on the softball team). It wasn’t entirely clear because they didn’t address it directly.

While the practice itself was a bit disorganized it wasn’t anything crazy. However, watching and listening to how the coaches talked, especially the couple, to each other and their own children, was alarming and seemed unhealthy. My impression of the coaches was that they lacked maturity and I’m worried that the wife, in particular, may be volatile, especially in a situation where emotions get the best of her.

After practice was over one of the other girls on the team asked the head coach if they were a boy or a girl, to which the coach didn’t answer directly, and the girls mom immediately scolded her. Shortly after this the coaches approached my wife and I and asked us our opinion as to how they should handle addressing the issue with the team and the parents. Both our girls were standing right there with us as the coaches talked. The fact that they openly addressed it to us, complete strangers, with no regard for the fact that our kids were right next to us, showed a complete lack of situational awareness and reinforces my feeling that they aren’t very mature. It put my wife and I in a very uncomfortable situation. We had not yet had a talk with our girls about transgenderism, homosexuality, or several other alternative lifestyles within society, primarily because we feel they are too young to fully grasp it.

Now our hand has been forced and we will have to address it. Our family is active within our church, our faith is important to us and we are cognizant of our responsibility to raise our daughters in a way where they will be able to stand on their own as they grow up. While my wife and I don’t agree with or support trans ideology or lifestyles, we also embrace the fact that we are called to love others in such a way that Christ’s grace and influence in our lives shines through us, and we are teaching our girls the same. We aren’t actively trying to shield our girls from everything in the world we disagree with nor do we look down on anyone who chooses a different lifestyle.

Additional context for this particular situation is that we don’t have any other leagues in our area so this is the only softball option for her. Our dilemma is this: do we keep our daughter on the team at the risk of normalizing a lifestyle and ideology that we don’t support, knowing that we can’t be within earshot of everything that is said on the field, and potentially exposing her to toxic coaching or do we pull her off the team and she misses the chance to play softball for the first time, something she has been very excited about since we brought it up? I’m curious how you view and might handle this situation, both in regards to the issue of transgender coaches for youth sports as well as toxic coaching in general.”

This situation doesn’t seem that complicated — the coach should have just said he was a boy and moved along when the question was asked by the eight year old girl. It shouldn’t be a surprise that young kids have limited filters and say exactly what they think. These coaches should have known a question like this might arise, especially if their gender isn’t readily apparent, and they should have also understood that explaining something like this to young kids isn’t complicated.

Just say what sex you identify as and move on, the kids will accept it for now. You could even make a joke about it. “I understand I’m pretty like a girl sometimes, but I’m a boy!” Boom, the story is over for the most part with the kids.

I’ve coached eight year old’s. They have no concept of sexuality and don’t understand, at least not most of them, where babies come from. Most of them, in fact, still believe in Santa Claus at these ages. They know there are two genders, but that’s essentially the end of their knowledge. And, to be honest, it’s not uncommon for girls to play on boys baseball teams at this age.

Heck, last year the best player on our ten year old baseball team was a girl. She was a monster. The boys were afraid to hit against her because of how hard she could throw and she could also hit the ball farther than any of them. Plus, she was a great catcher.

Until puberty happens, there isn’t really very much of a difference between boys and girls at all. In fact, many of the best athletes are often girls at young ages. So as someone who has coached young kids, this is just not something that needs to be brought up at all. The fact that they then brought this question to you — in front of the kids — adds to rather than detracts from the awkwardness.

Your girls don’t need a crash course in gender identity at this point in their lives. This coach identifies as a man and is with a woman and they are the dad and mom of one of the kids on the team. This should have been an easy question to answer and it’s all the kids needed to hear.

To be charitable maybe the coaches are hyper sensitive about ensuring they handle this issue correctly and that explains their awkwardness, but if they were this sensitive why not ask to speak with the parents without the kids present before or after the first practice? That would have been the best option to address this with the parents beforehand.

Plus, I think most people, regardless of age, just accept the gender of whatever someone presents. If you’re dressed like a man or woman, I’m not Crocodile Dundee genital testing you, I’m just presuming you’re what you say you are.

As for the temper issues, presumably whatever little league exists in your kids hometown has okayed these coaches as instructors. I can’t speak for what kind of background checks they do on coaches in your league, but as a parent who has coached many years for my own kids, we have to submit to background checks to ensure we don’t have any red flags in our past that would render us unable to coach young kids. Given the liability issues at play for all youth instruction, I would presume that is fairly standard at this point for all leagues.

So while they may not be great coaches or have perfect control of their tempers — I’ve coached for years and am certainly not a great coach and have been known to utter a curse word now and then when our teams collapse, which happens regularly — I think the risk to your oldest girl is minimal.

Your choice here is pretty straightforward, pull your oldest girl out of an activity she is excited to participate in because of her coaches — which would create its own larger scale dynamic because you have to explain that decision to her too — or simply permit her to play softball.

I’d personally let my own kids play in the situation you describe here.

But I’d also have a conversation with the coaches and explain that they need to tell the kids they are the dad and mom of the kid on the team and not get more specific than that. Again, if this were middle school or high school age kids, I think a conversation explaining themselves could be appropriate, but at ages eight and six it doesn’t feel like that’s necessary or, frankly, appropriate.

What I’d tell my own kid in this situation is that there are many different types of families and we will talk about them in the years ahead, but that doesn’t matter for now and she should just focus on having a fun softball season.

With most kids, that’s plenty.

“I’m writing to you in a unique situation and I need outside council. I just turned 25 and make pretty great money for my age. I’m on a scheduled raise program with my job and am guaranteed to be making 6 figures in 18 months. I work for a very large, well known, corporation here in the southeast.

I understand 100k doesn’t go quite as far as it used to but that’s still pretty great money for a 26 year old. I like my job when I have work and am really good at it and only go into the office typically 2 days a week.

I understand that this would be an ideal scenario for so many people and I feel bad complaining but here’s where it gets interesting. I finish all my work those days while I’m in the office and have absolutely nothing else to do when I work from home. I’m talking 0 emails in the inbox type done. People above me don’t give me more work because that is just more work they’d have to review. The 3 days or so I work from home I just watch sports, read books, or socialize with friends. I understand that this would be an absolute dream scenario for most people but quite frankly it gets really boring. My family is very blue collar and does not understand corporate and office culture so I can not talk to them about this. My friends mostly make less than me and work harder so I feel guilty complaining. I am afraid I am wasting away my potential. Am I nuts for wanting to look for a new job?”

Oh, you poor bastard, you make six figures at the age of 26 and only have to work two days a week. How will you even manage to get out of bed tomorrow?

Here’s the deal, just about everyone reading this right now would love to sign up for your job. But I understand why you might also feel a bit bored or unfulfilled. Especially given your age and the fact that you don’t have a family yet. At this age, your career can and should be a massive part of your existence. It’s why I always advise young people to work their asses off. Before you have a family is the time to truly advance yourself. You have more free time now than you will for decades to come in the future.

You think you’re busy when you’re single and 25 years old, but you really aren’t.

Trust me.

So here’s what I’d advise — there’s nothing wrong with looking for a new job, but don’t limit your growth to things that occur at work.

You’re fortunate to have a huge amount of free time to pursue other interests and make yourself more valuable as an employee in the process. Rather than seeking for your current employer to fill up your days with work, why not fill up your days with things that you’re especially passionate about?

That could mean adding a degree through an online program — maybe an MBA? — or it could be something that makes you physically or mentally stronger in other aspects of your life. Read more to get smarter and expand your skills or set a physical goal of getting in better shape or running a marathon, find challenges that exist outside of your work responsibilities.

Heck, if you really want to be industrious, could you get another remote job and try to balance two different “full time” jobs? If you’re only needing two days to do your job now, imagine if you had another job to double your income. That would be a heck of a challenge to manage. Maybe you’d love that.

Sure, you might have to hide this new job from your current job, but given how desperate companies are to hire right now, it seems like you have the ability to manage two full time jobs right now.

Final thought, it has been my experience that companies who have highly paid employees without enough work to give them often have lay offs coming in the near future. So I’d brace myself for the possibility that my job could be replaced if I were you. After all, if you’re making six figures with guaranteed raises built in while barely working, how much value are you really providing to the company? And if you’re feeling this way, how many other people at the same company are also underworked and overpaid? Likely many people.

That suggests the company could probably be far more profitable with far fewer employees.

I’d keep that in mind as I looked for other career options to pursue.

Because this golden goose of a job may be about to turn to fool’s gold.

Okay, I’m off to pick up my kids at school. Send your anonymous mailbag questions to,  anonymity guaranteed.

And, as always, thanks for reading and I hope you guys have fantastic weeks.

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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