Anonymous Mailbag

It’s Tuesday, which means it’s time for me to solve all the issues in the OutKick world. So let’s get to it.

But first, we’ve got an incredible NFL Draft offer. Bet $5 on Trevor Lawrence to go No. 1 overall on Thursday, which is a total certainty, and you win $100. That’s a 20-1 payout for new users with zero risk. It’s free money. So go get your bets in today.

Send your anonymous mailbag questions to, anonymity guaranteed.

Okay, here we go:

“I have a bit of a predicament. I am a female in my early 30s from a Pac-12 school (will you please become the Pac-12 commissioner and save us!) with a successful professional career and a wonderful, caring boyfriend who is a year younger than me. He and I have dated for over a year, and we moved in together earlier this year. Our communication is great and we seem to care and love for each other equally. We have a great sex life, too, but that is where part of my question comes in.
My boyfriend told me early in our dating that he is bisexual. He has both dated and been sexually active with multiple other men since college. He told me his relationship preference is with women, and as I said, our relationship has been great. It’s been completely monogamous for both of us as far as I can tell, and his sexuality was never a concern for me (in full disclosure, I’ve had a few drunken nights in my past where I may have explored same-sex fun in the bed, too). That’s neither here nor there.
My question to you is this: he recently told me he very much misses the chance to be physical with another man – not pursue a relationship, just something casual from time to time. I asked if this meant that he wanted to try a threesome with me and another guy, and he said no, it was just something he is desiring similar to his past experiences and he doesn’t think it would be cheating since it would be with another man. I’m not sure how I’d feel about the threesome, but I’m definitely not sure what I think about him hooking up with another guy on his own even if it is casual.  He reassured me he wouldn’t do this without my approval, and I want to be supportive of his sexuality, yet I’m not sure how I feel about this sudden desire he shared with me.
Should I be concerned for the long term about our relationship? Should I tell him absolutely not? Should we give it a trial run and see how it impacts our relationship?”
First, this is a choice for you. You know your relationship much better than I do. But, importantly, this isn’t only about your relationship right now, it’s about where your relationship is going in the years ahead. You say you are in your thirties. Do you want to get married? Do you want to have kids? These things are important factors.
But let’s start here and first eliminate the sex of the person he’s asking to sleep with and just ask this question: are you okay with your partner having a sexual relationship with someone other than you? Essentially what he’s asking for here is an open marriage. You aren’t married, so I suppose this would be an open relationship. The first question you have to answer is whether you are okay with this.
Moving on from there. You, to your credit, were willing to explore his interest by offering to be involved in a threesome with him, but he rejected that offer and said he wants to be solo with another person. Assuming he’s being completely honest with you — that this hasn’t already happened, which I think it might have — he’s telling you that you, by yourself, aren’t enough to make him happy in a relationship.
So are you okay with that too?
It doesn’t sound to me like you are. But only you know this.
Second part of this: Let’s consider the same-sex angle here. If he wants to sleep with men, this is a desire in him you can never, ever satisfy, no matter how good of a partner you are. This desire isn’t going to magically disappear if you one day get married and have kids. Can you be in a relationship where you know you can never satisfy one of your partner’s deepest needs? (There’s also always the possibility that he’s actually gay and desires being with men over women full time. And that in his relationship with you, he’s attempting to conform with heterosexuality standards and that at some point in the future, he’s going to decide he’s gay and leave you anyway. You mention that you’ve hooked up with women before. I think that’s more common with women than it is with men. Put it this way, I don’t think a man accidentally ends up sucking another dude’s dick. That’s a pretty intentional move.)

So are you okay with him continuing to sleep with men outside of your relationship for the next several decades? Are you okay hiding it from friends and family? Are you okay hiding it from your kids? Have you thought about how you would explain to them that dad has boyfriends? These are challenging questions that go to the heart of what you see the future of this relationship being.

If you don’t want to ever get married or have kids, that’s one thing. It’s just the two of you. But if you are thinking about marriage or kids one day, I think you need to make calculated and intelligent choices here.

Your boyfriend has told you exactly what he wants from your relationship. That’s admirably honest of him, but in the process, he’s now put the onus on you to decide whether or not you’re willing to accept the parameters of the relationship he wants to design. While it’s honest, in some ways, it’s also very selfish of him. Because you haven’t made, at least to my knowledge, similar demands of him.

Only you know if you are or are not comfortable with his stated desires, but your email to me suggests a decent degree of discomfort.

It sounds to me like you know this guy isn’t the one for you and are trying to save the relationship.

I’d trust your instincts.

“I’m a 30-year old married man. No kids. Besides Vegas for my 21, I’ve never made much of a deal about my own birthday. I’m a happy person and I’m not an introvert, but anything more than a humble approach on my own birthday just feels awkward. Dinner with close friends and family is appropriate, but even that only sits right with me if someone else is doing the planning. 

I have a few close friends who still try to make events out of their birthday. They want to do things like out-of-state travel. This is multiple guys in my life who have no problem asking myself and others to sacrifice significant time and money for these trips. Sometimes I’m happy to go, sometimes I reluctantly go, and sometimes I can’t go.
It didn’t become something I wondered about until I heard one of my friends get butthurt. He was complaining to me that he goes on one guy’s birthday trip but the friend makes excuses and doesn’t reciprocate for his fishing trip. He was genuinely disappointed and I thought he was being too sensitive. It confirmed that these birthday guys are keeping tabs on who actually shows and who doesn’t. It’s ironic to me because I never have self-promoted birthday celebrations and these guys legitimately won’t even realize my birthdate passed by.  I couldn’t imagine how they would react if I held that against them. Am I being a grouch about birthdays? Or do you agree that self-promoting your own extravagant birthday bash is extremely narcissistic and actually makes people like you less?”
Let me start here: if you are a grown man and keeping track of which of your friends come to your birthday parties and which don’t, you really need to get a life. That’s not how adults should behave.
We have one party a year for adults, our Halloween party. We invite quite a few people and the people who can come, come. The people who can’t come, don’t come. Do you know how much time I spend keeping track of who comes and who doesn’t?
Because I’m an adult and I have a billion other things to worry about than whether people come to our party or not. If people don’t want to come to something, that’s their right. I’m not going to lose sleep over it. And I’m not going to disinvite them next year.
And that’s the way every adult should be.
Okay, onto your birthday question in particular. I think adults who are obsessed with their birthdays are really weird, honestly. I mean, I guess I kind of get it if you’re still single and have no kids — even then, it still feels weird — but once you have kids, the last thing you want, at least in my experience, is having to worry about adult birthdays.

We’ve thrown and been to so many kid birthday parties in the last decade that the last thing I want is to have to plan a major outing for a grown person’s birthday. There is one caveat here, however. I think for round numbers, which symbolize major life events, that can change, primarily because it’s an excuse to get friends together and have a good time. For instance, when you turn 21 in college, it’s a big deal. When you turn 30, 40, 50, 60, the big round numbers, that’s a good excuse to have a party for your friends too.

But that’s really all it is as you get older. A birthday is an excuse for a party.

And the birthday helps you set up a party several months in advance without seeming like a total weirdo. (The same is true for Halloween, Christmas, New Year’s, July 4th. Big event parties are great excuses to plan some fun.)

“I’m a music producer/songwriter who recently, after a decade-long grind, got signed to a major record label. It’s been pretty cool so far, but one problem I find myself running into on occasion is that I’m a conservative.  
The music industry, much like sports media, is insanely leftist as you might expect.  It’s littered with wokeness, SJW’s and coronabros.  As a reasonable person with common sense, I sometimes feel like a sheep amongst wolves. Whenever political banter arises in a studio or elsewhere, I try to bite my tongue but I’m just not wired to do that and I usually bring up a dissenting opinion.  
I’m always up for a healthy debate but I’m worried I may ruin my career if I trigger the wrong person.  Should I say what I actually think to these people or just shut the hell up? Also, I live in the NYC area and absolutely hate it but it’s the best place to be for my music right now. Do you think it’s worth sacrificing happiness/mental health in order to further your career?”
Congrats on the record deal and good luck going forward.
If you’re in the music industry, I’d move to Nashville.
As for your politics, I’m far from an expert in the music industry — or anything about music at all, to be honest. I’m tone deaf — but there are a massive number of OutKick fans in music circles. Especially in country music. Which is why I’d say Nashville is probably a better place for you to pursue your career than New York City.
As for your own career, I’d advise you to stay apolitical and focus on the quality of your work over everything else. But once you have an established audience and career, I’d say you can feel more comfortable saying exactly what you believe. I think cancel culture is beginning to crumble, and if you have a strong connection with your audience, it’s nearly impossible for you to be canceled. The people who truly like you aren’t going to suddenly abandon you, no matter what you say going forward.
But I think the best advice for everyone out there, regardless of profession, is just to focus on being great at what you do and let the external noise that doesn’t directly impact your work life be just that, external noise.
For most of us, politics is just external noise.
I’d focus on my craft, if I were you.
“A couple years back my wife and I both dieted fairly well and both lost a good bit of weight (it was needed). We tried to stick with that for some time, but we’re human and resorted back to some not-as-healthy options per se… Recently my wife completed a degree in higher education that was certainly no easy task. It took a few years but she’s doing what she loves now and it’s been worth it. However when she was in her last semester she admittedly stress ate a lot- certainly not knocking her here- it’s something I could never fathom doing. But she’s made comments recently about being unhappy with the weight she’s gained back. We both have somewhat hectic schedules, so sometimes you eat what you can and that can be fast food or something again that’s not as healthy. I’d like to encourage us to maybe not even diet- just eat better and not as much crap- and get back to exercising at least some. So my question is how do I bring this up to her without being a complete dick? It’s a delicate situation obviously.”
How do you tell your wife you think she needs to lose weight without her murdering you? Ah, an age old question that husbands for generations have attempted to answer. We’ve also gotten this question a ton in the anonymous mailbag over the years.
I think the only way is by focusing on yourself. If you begin the conversation by pointing to your own body and your own health, it’s likely she’ll come along for the ride. What doesn’t work is saying to your wife: “You look fat and need to go on a diet.” What does work is saying: “I’m getting fat and need to go on a diet. Can you help me lose weight?”
If you ask your wife for help, she’s probably going to provide it. And you saying that you’re feeling fat or overweight may prompt her to adopt her own self-reflection. She’s probably going to echo your comments. Because after all, even if you don’t regularly weigh yourself, everyone notices when a pair of jeans doesn’t fit any more.
Despite all the talk about fat shaming being bad, people who are fat know they are fat and wish they weren’t fat. They know they aren’t healthy and they want to get healthier. One of the best ways to make that happen is by doing it together.
Chances are your wife will follow your lead if you start to make healthier life choices, and she may criticize herself in a way you could never get away with if you begin by holding yourself accountable first.
So I think in focusing on yourself, you’re likely to lead her to focus on herself too.
It’s the only way, frankly, these conversations can happen.
Good luck.
As always, send your anonymous mailbag 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.


Leave a Reply
  1. Man, that first question is a doozy lol..

    Lady, abandon ship. Your man is gay. At least he’s honest but the fact he declined a 3-some with you is the nail in the coffin. Not only that, you’re substantially raising your risk exposure to HIV. Drop kick his ass to the curb. Lose the zero and get yourself a hero lmao

    • Well now to be fair I can see celebrating up to your 21st birthday, I mean it’s the first time you can legally go out and drink, but grown men having parties because Gunther just turned 37 is borderline mental….same as celebrating New Year’s Eve. Do fireworks really mean that much to grown adults? It’s an amateur holiday. Where guys who drink once a year get wasted and become obnoxiously annoying after 3 beers.

Leave a Reply