Anonymous Mailbag

It’s Tuesday, and I’m here to solve all the problems in the world for the OutKick universe.

As always, you can email me your problems at, anonymity guaranteed.

Tomorrow, I’m scheduled to play golf with John Daly down in Birmingham at the Regions Classic so I’m trying to get everything taken care of in Nashville today, and it’s a bit of a whirlwind. But if you’re in Birmingham, tomorrow should be a fun day.

I’m teeing off right after my morning radio show ends.

Okay, here we go with the anonymous mailbag:

“My brother has been dating a bisexual girl for about a year. He knew she wasn’t 100% straight when they started dating, but he was down with it because she is super hot. Even though I’m a mom now I can see the appeal to my brother of a hot college girl that swings both ways.

But my brother’s girlfriend recently came out via social media as being ‘gender confused.’ She cut her hair very short (same haircut as my brother), STARTED DRESSING LIKE HIM- button down shirts, cuffed jeans- and told him she isn’t sure if she is male or female- now identifies as ‘pansexual’ and is beginning the journey to figure out her gender. I read him applicable parts of your answer to the anonymous mailbag question last week -the girl dating a bisexual man who wants to sleep with men- and he agreed that not only does he not want to gamble investing time with a girl who might wake up one day and decide she’s a man, but it’s just too weird of a situation for him. He’s been thinking of ending it for awhile- they’re long distance and the novelty of dating a hot bisexual wore off when she started dressing like him. We talked last night about the best way to end the relationship but my fear, and his too, is that he will be labeled a bigoted homophobe. To use his words, he is a ‘cisgendered male attracted to feminine women who identify as female’ and doesn’t want to be with a trans-man should she decide she identifies as male.

I’m not sure how to advise him when or how to end the relationship. She graduates this weekend and has a flight booked to visit him the following week. She is a sweet, albeit confused girl and he doesn’t want to ruin her last week of college but also doesn’t want her to visit him. My husband told him to end it now, tell her he isn’t into her ‘gender journey’ and to move on. I normally advocate for telling the truth in any breakup, but knowing that she was a bit unstable before this gender confusion, I feel like he should be more careful with his words and mindful of his timing so he doesn’t come off looking like an asshole. In a world where every sexual preference is celebrated and accepted with the exclusion of the straight male, when and how do you advise my brother end things with this girl in a way where he isn’t accused of being homophobic?”

I’d let her graduate, let her come for a visit, and then have a face-to-face conversation with her to end the relationship.

I wouldn’t make it about the girlfriend’s perspective, I’d make it about your brother’s life choices. He should say that he’s not ready for a serious relationship and explain why that is. To be as clear as possible, he needs to make the breakup decision entirely about his life choices, not her life choices.

Sure, she could lash out at him on social media and accuse him of not supporting her lifestyle choices and being a bigot, but that would make her look bad too. Which is why the best plan is to make this breakup decision entirely about his life choices, not hers. If he does this, I think the chances of her flipping out are diminished substantially.

Having said that, I think doing the breakup over the phone during her graduation week would be unfair to her. He needs to have a face to face conversation that, hopefully, can leave the two of them on as good of terms as possible going forward. (He should say he’s been having doubts about the relationship, but wanted to see her in person before he made a final decision. So she doesn’t think he flew her to visit just to break up with her.)

While her circumstances may be unique, she’s a recent college grad and so is he. Ultimately this is what happens with most college relationships. They end with one party upset they ended. There’s no reason to make this exit any more dramatic than necessary. He needs to stick to the script. This is about him, not her.

“I am a recently divorced father of a very precocious and intelligent five year old boy, of whom I have primary custody. We are currently living with my parents to save on expenses, and I try to help with my father, who is in declining health. While I am not exactly thrilled with the living situation, it allows me to give my son a stable household while working a full time job.

The other advantage it has afforded me is the opportunity to send my son to private school. With the public schools becoming ‘woke,’ this has become a priority of mine. The obvious drawback is venturing into dating again while living with my parents. Not a lot of women are interested in the guy pushing forty and living with his parents.

I’m not ashamed of my choice, because I’m investing in my son’s future, but there is a part of me that is resigned to loneliness and celibacy. Please tell me that I’m wrong, and that a guy in my situation might find love again.”

I’m not an expert on the divorced dating scene and hope to never be one, but I would think most women you’d date would find your decision admirable. That’s because most women are looking for stability and steadiness in a man, particularly if they are also divorced.

Which is why I’d think most women would consider any man who gets primary custody of his child and then takes care of him on his own incredibly impressive and, honestly, sexy in its own right. So I don’t think you have anything to apologize for at all. Quite the contrary, honestly.

Your email, however, suggests that you feel like you do have something to apologize for. So I’d just own your life choices and not run from them. You’re past the point of trying to look “cool” and are making the best decisions for your son and parents. That’s what adults do.

Sure, you could spend a ton of money and live in a great apartment or condo in a popular area of town with single people, but that would require your son to attend a school you don’t like as much and it would leave both he and your parents without the same support structure they have now. Adulthood, to me, is about often putting others first. That’s the very essence of what fatherhood — and motherhood — really should be, a selfless pursuit of giving your children the best possible path forward in their lives.

Now I’m not going to sit here writing and pretend I’m anywhere near a perfect father, but my goal is to be as good of a parent as I possibly can be. And I think I’m better at being a dad now than I was when I became a dad for the first time 13 years ago.

I don’t know you at all, but just based on the parenting choices you’re making, it sounds to me like you’re doing that. I wouldn’t brag about the choices you’re making, however, with women. I’d lead with it in a self-deprecating fashion. “I’m every woman’s dream, a divorced dad with primary custody of his five year old who lives at home with his parents.”

Women like honesty because most men lie to them all the time. And they like men who are honest and funny even more.

Just be honest about your life. I think you’ll find that, far from judging you as lacking, an awful lot of women will find your life choices very attractive.

“I’m a tenured professor at a very large University in the Southwest. I’m a die hard Trump fan and very conservative when it comes to politics. However, as you know, the world of academe is more woke than a crying baby at midnight. Daily, I get emails from administration about woke issues and even how we should celebrate the outcome of the Chavin Trial. It is so hard to bite my tongue. But I try to practice what you preach and ‘focus on my work’ and teach to the best of my ability and do the research required of a Professor.

My question: I teach very large classes and students often ask me about my opinions on things outside of the class content. Recently, a student during class asked me my opinion on the Chauvin/George Floyd trial and I deflected because I realize that if I told the student what I really felt it could cause problems for me. On one hand, I want to be authentic to my students and share my opinions. On the other, I have a family to support and don’t want to lose my job for sharing my political opinions when asked. In this day and age, even tenured professors can lose their jobs if they don’t agree with the ‘woke’ message. What would you do in my situation?”

I’d use questions like these as an opportunity to address the class in an open discussion you moderate without sharing your own opinion. This student you reference asked your personal opinion, but why should your personal opinion matter on a subject like this?

So here’s how I’d respond to that if you don’t want to find yourself in the crosshairs of the woke police. I’d say, “I try to avoid answering questions about my own personal opinions on hot button issues because I see my job as being to give you guys the tools to make your own opinions stronger than they otherwise would be. I don’t want to artificially influence your opinions because you worry that in order to get a good grade in the class, you have to have the same opinions as me. In fact, I see opening up your minds to make better arguments as one of the primary purposes of college in general. So you tell me. What do you think about the trial?” (This is assuming the class has something to do with a subject like this. If I were teaching astronomy, I wouldn’t stop class instruction to discuss hot button political issues. But if you were teaching history or political science or a course like this, I can see how it could be relevant.)

After she answers with her opinion, you can then allow the conversation to be led by the students themselves instead of you. Your job in this construct would be more like a referee in a game than it would be a lecturer. Your job is to moderate the conversation, essentially, not to drive it with your opinion.

One instructive idea I think would be interesting for the students is to let students vote as if they’d been on a jury in the Chauvin/Floyd case in private and then ask them to raise their hands in public on the same question. My bet would be there are widely divergent totals. That could lead to an interesting discussion about the difference between public and private opinions and how that can impact public discourse.

Again, these are just ideas.

In general, I would avoid giving my personal opinions on flashpoints of culture and try to use my classroom as a laboratory that’s open to a wide variety of ideas. That’s the essence of the college experience.

“Wifey and I had our first born 10 weeks ago and have been looking to buy something out in the suburbs (New Jersey with a NYC commute) now for almost 2 years. At first we lost out on 2 houses which both had 4 other offers on them, which I am told is pretty normal. Then COVID happened and the interest rates dropped so dramatically. 13 months into this COVID world and last week we put a bid onto our 11th house. We went very aggressive and went 45k over asking. The owners accepted an offer for 107k over asking. The house had 31 offers in 72 hours. At this point it’s just lunacy. My question is, how much longer to do you think we are going to see sub 3.0% interest rates and what do you predict for the short term and long term effects from the last year will happen? Potential for another housing crash?”

I think interest rates are a big part of the housing demand, but I also think this is a function of how few houses are on the market in general because of COVID fears.

If you go look at housing inventory levels — that is, homes for sale — they are down dramatically. There just isn’t enough supply for all the buyers out there.

I’ll give you a personal example. There is hardly a single house for sale in my entire Nashville area neighborhood. What’s more, there are almost no signs that ever go up offering homes for sale. The demand is so intense that as soon as one goes on the market, it’s gone before it even hits the official listings.

I think as the COVID fear porn recedes, more people will emerge and start to consider moving and/or putting their homes for sale and allowing strangers to walk through their houses. I think COVID is the primary reason inventory is so low. Lots of people don’t want strangers in their houses.

But I know there are a ton of you out there trying to buy new homes, especially if you recently had children or suddenly found yourself trying to work alongside a spouse all day in a tiny condo or apartment, as many of you did.

I think over the next year, the prices will moderate as the inventory increases.

One caveat, however. I’m nervous about inflation. I was barely even been alive — I was born in 1979 — when inflation was a major issue in this country, but we have a tendency to forget about dangers out there if they haven’t arisen in a couple of generations.

The government is printing and borrowing money like mad men. At some point, these decisions tend to catch up with you. There are many people now who argue deficits have no consequences and that interest rates are always going to be low. I’m skeptical of that line of thinking because it doesn’t match the historical record. So it’s possible housing prices could rise substantially, not based on a traditional metric, but just because inflation is beginning to run rampant.

In that scenario, a 3% mortgage is great for those who have them locked in. But who is going to be able to buy a house if inflation takes off and mortgage rates skyrocket? So my advice is always this, don’t buy a house unless you can afford to live there for at least five years. Just don’t do it. And ten years is even better. Many people buy at the absolute extreme edge of their finances and set themselves up for a disaster if things don’t go perfectly.

Don’t do this.

My advice is always buy a home at your last salary. That is, the one before you got this raise. Living a job behind your means is good advice, no matter what your job is.

“Hey Clay, I recently lost my mother to cancer. No doubt it’s been a very difficult time for myself. She did however leave me with a decent amount of money. I’ve always lived within my means. I make just a fair salary and take care of my family. How would you use or invest the seven figures that I received? My first initial thought was to just put everything in the bank and sit on it. California housing is out of control so I don’t plan on investing real estate right now. Would like your insight.”

If you’ve inherited this kind of money in a lump sum, you need far better advice than from someone like me. A certified financial advisor can analyze your existing lifestyle — kids, mortgage, future salaries at your job — far better than I can based on a short email.

My general advice would be to buy S&P 500 index funds and just sit on them. But the market has been on such an incredible run recently that I don’t know that I’d go rushing to buy right now. But you also don’t want to just have that kind of money sitting in a bank account drawing almost no interest.

Which is why I’d consult multiple financial professionals, share your life goals and current life situations with them, and then pick the financial professional you like the best as an advisor. (I’d go with an employee at a big name company because you don’t want to get fleeced by someone who you should have never given your money to in the first place.)

Good luck.

As always, thanks for supporting OutKick and send your questions to, anonymity guaranteed.

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.


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  1. ‘My brother has been dating a bisexual girl for about a year. ‘

    I didn’t even need to read the rest…get your bro out of that tornado of chaos Saving Silverman style.

  2. In fact if you anon mailbag Clay with…’my boyfriend or girlfriend has (insert abnormal sexuality here)’…the most simple advice is ‘get out’. It’s mental illness.

  3. I don’t think Clay really leveled with the 40 year old living with his parents. Now hats off to him for taking care of his kid the best way he sees possible but a 40 year old living with his parents and a 5 year old kid…..he may very well never get laid again.

  4. Dear College Prof:

    I think it’s important to view your question in regard to the subject that you teach. If you are a math or chemistry instructor, I think you should not really ever be advising students on your political opinions either inside of our outside of class.

    I have taught law students and medical students and I always felt it was my goal that no student should be able to tell who I voted for or which political views I personally held. I always tried to challenge their thinking and beliefs by presenting opposing or “devil’s advocate” fact patterns, in order to get them to support their conclusions with facts (or law).

    That being said, if your subject of instruction is sociology, political science, or perhaps history, then obviously I would totally agree with the Clay The Wise One and suggest that you can moderate a FAIR discussion of issues, provided that is a method of instruction with which you are comfortable.

    When some woke-ass idiot student blurts out the inevitable “well all cops are racist murderers,” then you have your true teachable moment to let the kid know he is free to hold any opinion that he/she wants, but making perjorative, unsupportable statements isn’t going to convince anyone of anything except that you’re not very well-informed, and arguments not based on facts are just (weak) opinions.

    Any school that would give a tenured professor a hard time for fairly moderating a discussion in class, (without injecting his own personal opinions into the discussion) is clearly not an institution of “higher learning” that you would probably want to be associated with anyway.

  5. Boy, if I were the guy in NJ, I wouldn’t be buying a house if I didn’t need to (eg, unless moving to a new city for a job). Prices are out of orbit, inflation on lumber alone has added $36k to the price of a newly-constructed home. He is going to be financing a house with a hugely inflated price.

    Interest rates aren’t going anywhere simply because at $30 trillion plus in debt, the Fed cannot raise interest rates beyond a few points. Any more than that, and Congress would have to cut “entitlements” to pay interest on the debt. They ain’t gonna let that happen.

  6. NY/NJ guy: Move to a state where property taxes are low and where no income tax exists. These fascists Cuomo and Murphy are only gonna make things worse for you if you’re a home owner. Get out before you’re in a DemoKKKrat death camp…

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