Anonymous Mailbag

It’s Tuesday, which means it’s time for me to solve all the problems in the OutKick universe.

So let’s get rolling with that.

As is always the case, you can email your questions — anonymity guaranteed — to

With that in mind, here we go:

“Hey Clay, so I have a odd life situation that I need your advice on. I am a 30 year old single male. There’s a girl that has been my good friend since college when we were both 20. We have had a friends with benefits type of relationship for the last decade. The relationship basically looks like this: I spend the night at her house usually at least one night on the weekend and occasionally I’ll spend the night during the week if one of us is wanting our needs met. Outside of that I’ll on occasion go out to dinner with her or if one of us needs a date for a social event we will take the other. We also do text fairly regularly and are really good friends. We are both very career oriented and financially successful. We have never dated or anything outside of this strange friendship because we feel like we fulfill each other’s needs right now. The thing is I am 30 now and looking towards getting married and I’m not really sure how I tell her that because I know that it will have to stop things between us. I care deeply about her as a friend and someone who has been my sexual partner for the last decade but do not want to marry her.”

My first question here for you is what makes you think this girl wants to marry you? Has she ever suggested that? Because it doesn’t seem like she’s demanding much from you at all. In fact, it seems like she’s intentionally kept you in the friends with benefits category for a decade.

If anything, this is a question she should be asking me, not you, since she’s thirty and has more of a ticking biological clock than you do. So the first question you need to answer is this: why do you think telling her you aren’t interested in getting married to her is necessary? It sounds like she’s not that interested in getting married to you either. If she were, I think she would have suggested something more than the casual relationship you guys have had over the past decade.

My second question is, have neither of you ever dated anyone else for the past decade? That would seem to provide some guidance here as to how to handle the situation going forward. If you haven’t, that’s very odd too. Regardless, right now it doesn’t seem to me that she’s stopping you from dating other people. Presumably in order to get married to someone, you’re going to have to be dating other people to find someone who is the right life partner for you. Until you reach the point where you are in a serious relationship, I don’t see any reason why you need to have any conversations about the future with her at all. At least not if both of you are happy with your present situation. Now if you eventually reach that point where you do want to date someone else seriously, that’s a conversation you’d need to have regardless.

But for right now, I don’t see how you’re treating her unfairly.

Now maybe if you had a serious conversation with your friend with benefits of the past decade and explained that you’d found someone you wanted to date exclusively, this girl would suddenly bare her heart and soul to you and say she wants something more serious. But so far, that hasn’t happened in the past decade. I’m not sure why you’d expect it to happen now. At the present time, it feels like you’re putting the marital cart before the horse.

Find the girl you want to date seriously first, then you can worry about ending your current situation. As is, it doesn’t feel like you’re leading this girl on at all. She seems comfortable with the relationship you both have. As long as that’s the case — and you are too — you aren’t doing anything wrong.

“I am attending a bachelor party this summer for one of my best friends from college and I am a groomsman in his wedding.

Here is my predicament. One of the days we are planning on buying tickets to a room at the track for all-inclusive food, beer, great view of the track, etc. However, you need to be vaccinated to attend – no exceptions (a negative COVID test doesn’t count). Full disclosure I am not vaccinated and was not planning on getting the vax – at least not just yet. I am 29 years old, in great health, most likely already had the virus and don’t believe it is necessary for me to get a relatively newly produced vax to prevent myself from getting a virus that I have a 99.9999% chance of beating. For me, the ‘protection’ is just not worth the potential and unknown risks in the future.

To put things in perspective, this group of friends is made up largely of liberals. I am the only one who is not vaccinated. I am also the only republican in the group. I thought that was relevant to say since, as you know, I could face harsh judgment and potential exile if they find out I am not vaccinated.

My question is, do I just suck it up and get the vax? I really don’t want to complicate things and have the entire activity cancelled on my behalf. I also would hate to disappoint my buddy if for some reason I can’t attend, but at the same time I don’t want to compromise my beliefs and potentially my health just to attend a day at the track.

The weekend is Thursday-Sunday. I was thinking maybe I can arrive Thursday and make up an excuse to leave Saturday and miss the day at the track (I don’t bet on horses anyway) or I could potentially try and go under age 21 mode and use someone else’s vaccination card. However, I wanted to get your thoughts and see how you would handle this situation.”

First, as I’ve said for months, I think if you are at high risk from COVID, you should be vaccinated. My parents are vaccinated. My elderly relatives are vaccinated. If you are over 65 years old or have significant health-related issues that might leave you susceptible to COVID, then I think you should be vaccinated because you are at much more substantial risk from COVID than younger and healthier people.

But as I’ve been writing and talking about for over a year now, that isn’t the case for everyone. If you are young and relatively healthy, you had a nearly zero percent risk from COVID. And you still do.

I’m not anti-vaccinations. My kids are vaccinated for the diseases that are dangerous to children. But COVID isn’t a danger to young children at all, so I’m certainly not getting my elementary school kids vaccinated for COVID. So far, I’m not vaccinated either. I had an appointment to get the one shot vaccination, but on the day I was scheduled to get it, they pulled it from the market and I haven’t rescheduled an appointment.

However I did go to my local Kroger to see if I had COVID antibodies yesterday. And, guess what, I have COVID antibodies. Meaning I had COVID at some point in the past.

I suspect it was from all the way back in mid-November. Several people at my gym tested positive around then, and I woke up one NFL Sunday morning and felt kind of crappy. I had a low-grade fever for most of that Sunday, so I made a major sacrifice and stayed in my bedroom and watched NFL football all day. The next morning, I felt fine and did my radio show and TV shows from my home studios like normal. But since I hadn’t felt well, I kept my distance from my family for the next week to ten days and didn’t go anywhere outside my house.

After ten days, I went back to my normal activities.

If COVID hadn’t been going around, I would have considered it a 24-hour bug and not even thought twice about it. I would have gone back to my normal activities the day after my fever. I never got tested for COVID because I’d only felt bad for one day and I’d never gone and gotten tested, for instance, to see if I had the flu or any other virus before. If I’d felt sick for more than a day or so, I might have gotten tested. But people were swarming testing centers back then, and I wasn’t in a hurry to spend a day getting tested for something I’d already recovered from.

So I just kept my distance from everyone and waited things out at my house. My experience with COVID was basically what the data suggested my experience as a healthy, non-overweight person of my age with COVID would be — a virtually nonexistent issue.

So I suspect I had COVID then, since it’s the only time in the past year I’ve had any symptoms at all. It’s also possible I got COVID some other time and was completely without any symptoms. Given that I now know I still have antibodies, I’m not going to get the COVID vaccine now because the purpose of the vaccine would be to give my body what they already have — antibodies to COVID.

The antibody test was easy to get, by the way. I just went to my local grocery store pharmacy and paid $25 for the test. They pricked my finger, I waited fifteen minutes, and then the pharmacist came out and told me I still had COVID antibodies.

By the way, here’s Jon Stewart yesterday pointing out what should be obvious to anyone with a brain: COVID came from a Chinese lab.

Okay, on to your specific question. Let’s start here: who is checking these vaccination cards at sporting events? I’ve never been to a sporting event in my life where I’ve thought the people taking up tickets were a particularly skilled group of people. And not once in my life have I ever thought, you know, if this person wasn’t taking up my ticket today, he’d probably be a doctor.

My point here is, I don’t think your average ticket taker cares much about your vaccination card. It just makes his or her job more difficult and increases the lines to get into the venue. So if you went the underage ID route, it may well work.

Now, to be fair, I haven’t yet had any event, sporting or otherwise, I wanted to attend impacted by a vaccination requirement. But I did travel to Mexico and need to produce a negative COVID test to fly back. And do you know who checked that form? The Southwest ticket taker in Mexico. I just handed him a printed off piece of paper from our hotel. He looked at the form for ten seconds and waved us through. There’s no way he had any clue whether I’d really gotten a COVID test or not.

I’ve actually been tested five times for COVID now, all negative, in order to do different events. I was tested at the White House before we met the president, in Mexico before we returned to the United States, back in the summer in Tennessee to see what the testing process was like, before Wrestlemania, and then recently before doing a TV show.

My point here is, I don’t think these vaccination (or test) requirements are being strictly enforced. So I’m not sure you would be excluded from entry, even without your COVID vaccination card.

Having said all of this, this is really a personal decision for you: how much do you want to attend the event with your friends? Because the only way you can 100% guarantee you are going to be able to be there with them is to get vaccinated. And ultimately neither I nor anyone else can answer that question for you. Which matters more to you, being with your friends at the entire bachelor party or not getting vaccinated?

The choice is yours, my friend.

“Today my boss asked to meet with me. Within 30 seconds of our discussion, he told me he was letting me go, and asked that I resign so that he would not have to fire me. According to our talk, his reasoning for doing this was not that I was a lazy employee or that I was not reliable. His reasoning was that I am not assertive enough for the role and that, in his opinion, I require more structure and direction that my role had access to. As a 22-year-old recent graduate who just lost their first job, I am naturally in shock and am looking for any advice I can get. Growing up, my friends introduced me to your content early on and I was hooked instantly. My educational background is a BBA and MBA with a focus in finance (especially in the field of investments). I am not even sure at this point if I am convinced that business would still be my biggest passion in life. I guess the reason I am emailing you is because I remember that you started your career in media early on despite studying a different field and I believe that you can give me sound advice as to if that’s something I should pursue or if I should stick to the field I am familiar with. I would greatly appreciate any and all things you have to say.”

Did you like the job you had before you were fired?

If the answer is yes, I think you have to keep your chin up and persevere. Many people who have been incredibly successful have been fired early in their careers.

Heck, like many of the people reading this right now, I’ve been fired before. For people who don’t know my entire story, FanHouse, where I worked over a decade ago, shut down in the winter of 2011, right after Auburn beat Oregon to win the national title. I loved my job there, but then, boom, I got a call letting me know my job, and most other people’s jobs there too, didn’t exist anymore.

Just like that, we were all fired.

We got no warning at all.

But it ended up being a blessing in disguise because that’s what led to me starting OutKick.

I mention that because most people out there, regardless of their profession, have had situations like this happen — a moment where you lose a job and have to find something new to make a living. For me, that led to OutKick. If FanHouse never shut down, I doubt I would have left.

I might even still be there now.

And OutKick might have never existed.

Which means the best thing that ever happened to me in my career was getting fired by FanHouse.

What I knew was I loved what I was doing. So I didn’t want to start something else brand new. The question you have to answer, and only you can answer this, is: did you love the job you had? (What I always tell young guys or girls working a job is this: look at your boss’s boss and determine if you think you’d like his or her job. And I don’t mean just the money that person might make. I mean the actual job he or she has. Is it something you’d like to do? If the answer is yes, you’re in the right profession. If the answer is no, you’re probably in the wrong profession.)

Plus, if you’re 22 years old and are getting fired, honestly, the company that hired you made a mistake hiring you in the first place. I doubt it was you at all. Because no one is that good at their job at 22 years old. You just don’t have the skill set to do well at most jobs coming straight out of college. So that’s a flaw in their hiring process more than it’s a flaw, probably, in your work ethic or skill set.

Which brings me back to the original question. Did you like your job? I liked what I was doing at FanHouse and wanted to continue to work in sports media. So I founded OutKick.

If you like your job, I wouldn’t run to pursue another career direction just because you got hit with some adversity. Because adversity is going to exist in any profession you pursue. Whatever new career you pursued would feature adversity too. I loved my job — and was good at it too — but it didn’t stop me from getting fired.

So do you want to make a living in your chosen industry or not? That’s a question I can’t answer, only you can.

Good luck.

As always, thanks for reading OutKick. You can 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.


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  1. FWB:

    Dude, you’re practically dating this chick already. I’d be interested to know why you wouldn’t want to pursue a more serious relationship at this point. Checks off 2 big boxes; 1) independent/financially stable 2) low maintenance.

    A general rule is I go by is bad pussy will make me leave but good pussy won’t make me stay. Clearly the sex is good if you’ve been hitting it for a decade and clearly she has a good enough personality that you don’t mind spending every weekend with her. If for whatever reason she isn’t wifey material then break that shit off and keep it 100. It’s gonna be hard to really explore finding other women if you’re catching multiple nuts a week from the same chick.

    • Yeah, I mean you’ve got a chick who evidently you get along great with, take her out to dinner once a week and she’s happy, evidently gives it up any time you want it….why the hell would you look for absolutely anything else?

      • Same age, same college, and has known her for 10 years. There is a missing piece to this puzzle… My only guess is she isn’t super hot? If that’s the reason then it’s a dumb one. Looks fade. I’d rather be with a 7 that I can conversate with and share my ideas and goals with than be with a 10 that has the IQ of a turtle.

        • I think the missing part of the puzzle is family. Sure, they go to social events together but what about the holidays/family events?

          I had a similar relationship in my 20s and we rarely even saw each others family. That was the ultimate issue when one of us (me) wanted more out of it. Ultimately, she ended what we had going, she met someone else right away and ended up married very soon after. Slut.

          • bahahaha the end to that story was great.

            She “met” someone else right away. She was scheming. I’m sure you’re better off my guy.

    • Completely agree with Tanner here. I don’t disagree with Clay on much, but I 100% disagree with his advice that you should find a girl first, then break it off. If you are absolutely sure you don’t want to pursue a serious relationship/potentially marry the girl you are with, break it off now like Tanner said, and be real. If you really want to be married and have a chance at a successful marriage, you need to lose your old habits now and start preparing for your future marriage in order to find your girl. That means, doing right by the girl you’re currently with and doing right by yourself and your future wife. Staying in a relationship for sex/selfish reasons is not going to help you find the girl you want to marry, especially at your age. 50% of all marriages end in divorce. I think my advice takes you down the path of potentially finding a lasting relationship and potential marriage. I think Clay’s advice prolongs your bachelorhood and keeps you in a selfish mindset, which is a mindset that leads to divorce. Good luck.

    • Totally agree with all these thoughts. Have the talk with her first dude. She’s a great friend, at least a good lay, and you like to spend time together. All the characteristics you list are prime spouse material.
      Go for it. Ask her where she stands. She may have friend zoned you because that is what she thinks you want. If FwB is what she wants then move on, and close that door.

  2. Why would the guy with all liberal friends even want to spend a day at a racetrack or anywhere else with the bunch of libtards
    You know they will bring up their usual propaganda spewing crap heavy on TDS that will never resolve

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