Anonymous Mailbag

It’s Tuesday, the college football season is officially completed, and I’m here to solve all the problems in the world. Yep, it’s anonymous mailbag time.

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

Okay, here we go:

“I’m hoping you can shed some light on a situation I’ve been experiencing with a group of close friends recently. My fiancée and I have a close group of friends which consists of 3 other couples, all of us are in our late 20s. One of the other couples is married, the other two are boyfriend/girlfriend.

Here’s the deal:

Lately, there have been some things going on within the group that have taken me by surprise. A lot of flirty comments (usually jokingly) between people in different couples. Sometimes it’s funny, and other times really strange. Then, a few weekends ago, my buddy’s girlfriend started flashing everyone (boobs) during a night where we were all hanging out and having some drinks. That same night, my other friend’s wife flashed us, seemingly feeding off the earlier flashing, and then the other girl in our group did as well. By the end of the night, each girl except for my fiancée had flashed everyone (it’s just not her style, nor is it mine). So this wasn’t a huge deal, I chalk it up to a close group just messing around after having some drinks.

Fast forward to New Year’s Eve, we were all together celebrating 2020 finally coming to an end. Long story short, my friend’s wife ended up kissing one of our friends (with his girlfriend present) on the lips. There was no tongue, but it definitely surprised me when I saw it. They just got married a few months ago, and it seemed strange to see her kissing our other friend. They were both kind of laughing about it and joking. My fiancée and I just kind of laughed it off and went on with the night. The husband and the girlfriend of the two that kissed didn’t seem too concerned or bothered by it.

What started with flirty and somewhat strange comments between these couples turned into flashing, then a kiss just a few nights ago. Does it seem like this could be leading to them becoming swingers? These are close friends of mine, so I figured I wouldn’t say anything until something more serious happens. Honestly I don’t really care what they do, I’d just like them to know I won’t be a part of it and I’d rather not be around when that’s going down. Am I reading too much into this?”

First, if three different women flashed you at a party, that sounds like a great party. Instead of being worried about what might be coming next, I’d be excited about what might be coming next. Heck, maybe the girls will start making out topless at the next party.

You poor thing. I don’t how you’ll recover from this.

Second, as long as you and your fiancée are on the same page with each other, I’m not sure I’d worry too much about what the other couples do. You guys aren’t interested in your fiancée flashing the group or in her kissing other guys or certainly in swinging with them.

I think the odds of a full-on orgy breaking out are low, but if it does, you guys are free to just excuse yourself, probably like you’ve done before when a couple starts making out in the room you’re in.

Plus, I’m not sure how you could figure out what the next step is without waiting to see what the next step is. I’d suggest you and your fiancée have a conversation about what might have to happen at the party for you to feel the need to leave, but that’s between the two of you, not you and the group.

It’s also possible that the swinging/group sex has already started, and you and your fiancée just don’t know about it. Maybe they’re trying to see if you are game to join in by their actions.

Or maybe everyone just gets flirty when they get drunk, and there’s not much more going on here.

What we know is that the other three couples seem fine with what’s going on, and you and your fiancée might not be. That’s fine. You can make your own choices. If their actions are interfering with your enjoyment, then do what all adults should do: choose to spend your time elsewhere.

“I’ve been spending most evenings (no overnights) with a man 15 years older than me. He loves me passionately…… Me? I love him as a dear friend and am good with a friends with benefits situation.

I’m a really private, quiet introverted person for the most part, while he’s the mayor of any place he goes, meaning he knows a ton of people and loves attention for his vast life experiences. I find his friends and associates a bit pretentious and shallow. I don’t mix him with my friends because they find him overbearing.

He has now offered to have me move in to a two-bedroom ocean view condo claiming he will give me space and I’ll have my own bedroom and bathroom. The rent would be split 75% (him) 25% (me). With my lease expiring soon, I had found a cute carriage house for one, yet fear I might be too isolated and know I do like and need company and socialization (besides my job).

I do enjoy his company and find him funny. However, I do not want to be joined at the hip with him (or anyone really). I’d rather be dating someone my age who wants to get together a couple of times a week. I have looked for years, but have yet to find someone copacetic with that who also has the qualities I find important: funny, athletic, and smart (meaning reads books).

Am I a simply a selfish commitment-phobe? Any words of wisdom?”

If this guy is in love with you and wants you to move in with him — even if you’re paying part of the rent — it sounds like he’s making a fairly substantial commitment to you. Meanwhile you aren’t that interested in committing to him, at least not right now.

So where do you see this relationship going and how honest have you been with him about the direction of that relationship? Because once you move in together, the seriousness of your relationship increases a great deal, at least in his mind, primarily because you just aren’t able to escape being together all the time.

Whatever decision you make is fine, but I think both you and he need to understand what’s involved in the scope of this relationship and where it’s headed.

Final point, I’m always skeptical of relationships where one side is in love and the other side isn’t. It feels to me like you are taking advantage of his feelings and leading him along. It sounds like you are getting what you want out of this relationship, but he isn’t.

That isn’t tenable in the long term, which is why I suspect you feel bad about the idea of moving in with him.

So I’d turn down the offer and maintain your independence. At the very least, you are giving him a clear signal that you are fine with the relationship as it exists now and don’t desire anything further.

“Hey Clay, I’m currently in the middle of 1.5 year relationship with a girl that I see myself one day proposing to and marrying. However, something that has been a small issue is that I do not find her best friend and their group of friends appealing at all. I mean every time that we go to visit them, I dread it for days. All of her other close friends are people I really like but I just do not vibe much with this crowd.

They are simply not my people and frankly, I’m really not sure what she sees in them. We don’t live in the same city or state luckily but that could change down the road. Any tips or advice here?”

First, why do you have to go visit her friends with her when it’s an out-of-state trip? It seems relatively easy for you to let her go spend time with her friends and for you to do your own thing with your friends while she’s gone.

Second, do we know if she likes your friends? She may be pretending, as many girlfriends and wives do, to actually like your friends too.

My point here is it’s not uncommon at all for someone in a relationship to not particularly like their boyfriend or girlfriend’s friends. After all, friends are often a window into who you’ve been in the past. You may have changed from that person to who you are in the present, and your partner may find the new you more appealing than the old you.

Let’s say you guys get married when you’re thirty. What are the odds you would have dated your partner when you were fourteen or fifteen? Maybe you would have, but the chances of that are pretty slim. We all change quite a bit, even if it’s relatively imperceptible, between 14 years old and 25 or 30 years old.

If that’s true in terms of whom we date, then it could also be true of whom we are friends with as well.

The bigger issue here, however, is you’re marrying her, not her friends. Unless her friends suggest something important about her that she might be hiding from you — are they drug dealers or meth heads, strippers or escorts? — then you will likely have less time to spend with friends once you get married and have kids. So your friends become less of a major part of your lives. That doesn’t mean you cease having relationships with your pre-marital friends, but it just means they are a bigger part of your life in your twenties than they are in your thirties and forties.

Once you get into your thirties and your forties, your life gets so busy with work and kids — for most of us — that you’ll struggle to get together very often. You may text or talk on the phone, but your day-to-day interaction dwindles.

And your lives change immensely as you enter into the work force, buy a home, and advance in life.

Which is why most of us, based on what housing costs, end up living around people who are fairly similar to us in lifestyle choices. For instance, I live in a neighborhood where a huge percentage of the people who live here are parents with school age children. That’s not coincidental. We’re here because of the life stage we’re in.

Getting married, at least in my experience, doesn’t change your social life as much as having kids does. Kids change everything, especially if you have multiple kids, because they are such a time vacuum.

Given that these friends of hers you have issues with don’t even live in your same town or state, I fail to see how it can be that significant of an issue going forward. Issues with, for instance, her family would be a far bigger deal and are less likely to be eliminated in the years ahead. But the friends? Getting married and having kids is going to make them matter less and less going forward.

My point here? You’re marrying her, not her friends. If you love her, just find ways to spend less time with her friends.

And certainly don’t travel to hang out with them voluntarily.

(If you can’t trust your wife to go out with her friends without you present, then you’ve got more significant issues than who her friends are.)

Final point: sure, you could raise this as an issue with her, but I don’t see it as very productive. Good luck with the fight that ensues when you say, “I don’t like your best friend or her friends.”

Plus, what’s your goal here? It’s pretty controlling of you to suggest that because you don’t like her friends, she should spend less time with them. Why do you have to like her friends at all? And why in the world should you get veto power over them? Think about it this way, how much would you resent her telling you she didn’t like some of your friends and that you shouldn’t hang out with them any longer? I just don’t like that move as a boyfriend or a girlfriend. It’s not about the friends. It’s about control.

And if you have to control someone in a relationship, it’s probably going to fail or be completely unhealthy.

So I’m not even sure what your goal is here, honestly.

The simplest solution, it seems to me, is just spend less time around those friends of hers.

“I followed your advice and invested fairly heavily in the stock market back in the first half of 2020. I bought MGM, Peloton, PENN, Tesla, Apple, etc. I sold some of the stocks I bought too soon but reinvested my gains and have made a substantial profit from my initial investments. I’m only 24 and I only had a few thousand saved up to invest, so I don’t have a ton of money at risk right now. But my question is what should I do with those stocks now based on how the elections went and the direction the Democratic Party may take us economically? I hope the direction they take our country is beneficial for regular Americans but I know you’ve talked about how the markets are more favorable during split party governments, so I’m a little worried as to what will happen to the stock market over the next few years.”

First, congrats on getting one of the best stock market buying opportunities of your life back in the spring.

I told everyone to buy stocks in March. If you bought the stocks I recommended — the sports gambling stocks in particular — you have made dizzying returns in a very short period of time. We truly may never see a buying opportunity like this for the rest of our lives.

I took some of my profits out of the sports gambling stocks just because they were so insane, but I’ve kept the majority of my money in the stock market because I’m 41 years old and have plenty of time to recover from any downturns that might ensue. You’re only 24, so you have even less reason to worry about the day-to-day movements of the market than I do.

I do think the market is likely overbought right now, but interest rates are so low I’m not sure what other options most people have with their cash.

My advice to everyone reading this right now, who is potentially new to the stock market or the idea of investing, is just to buy index funds, in particular S&P 500 index funds, unless you feel like you have a particular expertise in any area.

Back in March, I felt like I understood the dynamics of the sports gambling industry, and I analyzed the likelihood that sports leagues would find a way to play better than most people in the market. As the market collapsed in March, many were terrified that sports wouldn’t return to play in 2020. Based on my analysis of the sports market, which I felt like I knew better than most, I didn’t think that was likely and I believed the market had vastly oversold the sports gambling industry, which was poised to surge in the months ahead when sports returned.

And I was right.

I’m not claiming to be some kind of market savant. Far from it. But I do think that if you have a particular expertise in an area, you can sometimes spot market inefficiencies and take advantage of them.

But that’s only if you’re buying individual stocks, which is riskier than just buying index funds.

In the interest of full transparency, I typically share the stocks that I’m buying. Back in March, I hit a homerun with my recommendations, and I hope some of you profited off of the suggestions.

You’re only 24 years old, so I’d leave your money in the market, try not to obsess over the day-to-day fluctuations, and just let your money grow. In fact, you should be setting up a savings plan to keep rolling more money into the market on a regular basis so you can continue to grow your nest egg.

Good luck.

Great article on Big Tech today. On a scale of 1-10, how scared are you of getting kicked off Twitter or even having internet server companies such as Amazon, Microsoft, and Rackspace not allowing OutKick to be hosted on the internet?”

I try not to be scared of things I can’t control.

That doesn’t mean, however, that I’m ignoring the risk. I tweeted the other day to encourage those of you who like to read OutKick to bookmark our site and visit daily rather than waiting to see links on social media, and I did so for a reason.

A huge percentage of our audience comes to OutKick directly. Frankly, I wish everyone came here directly, and we didn’t even need social media at all.

That would be the ideal scenario.

I suspect that with the shut down of Parler, there will be many wealthy individuals who are committed to the free exchange of ideas and who are scared by what happened to Parler. I suspect they will create their own cloud computer infrastructure to ensure that sites aren’t taken offline based on big tech decisions.

So I’ve encouraged our tech guys to consider back up options in the hosting community that might be more libertarian in nature to ensure that we don’t get knocked offline in the future.

But ultimately I can’t control what big tech companies might do to me or OutKick. I can control only the choices I make. I think that’s the best advice you can give anyone of any age: worry less about what people might do to you and more about what you are doing.

I find that a huge number of people spend lots of time worrying about what other people or entities are going to do to them. As long as you aren’t facing physical danger — which is an entirely different story completely and should be treated seriously — it’s mostly wasted energy to worry about the actions of others.

“Control what you can control” is some of the best advice out there, but I’m not sure it’s given enough.

So that’s what we’ll continue to do at OutKick.

As always, thanks for supporting OutKick and continue to send me your anonymous mailbag questions at

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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    • I thought the same thing, Gary! Always thought being a writer for the Penthouse Forum was the best job possible. Just have to share a memorable one that was an oldie as a typewriter was involved. Seemed the boss had the hots for his secretary. Letter written by the “boss.” Anyhow, secretary had left for the day, or so he thought. He was in his office and unzipped the fly and proceeded to place his “manhood” in the typewriter to where the keys would hit it. Referred to it as both his “pecked pecker” and his “ink-stained inky dinky (not the best of self-compliments)”. Ah, those were the days …

  1. The Mailbag is always great … especially the pic of he bikini babes with Kingsbury … hubba hubba.

    The Athletic used to have, maybe still does… a “persona” known as “Faux Pelini” who did GREAT schtick like this. Maybe he could get Jason’s old office?

  2. I don’t get the draw of most of the questions in these articles, but as for the last one, Trump better pump some money into these potential non-leftist tech enterprises. He has the resources to do so and is the man who tore the mask off of all these crazy authoritarian fucks and led us to this point.

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