Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

The anonymous mailbag is back from vacation. Not doing the mailbags last week created an uproar from you guys. It was both gratifying and terrifying to see how many of you are building your work days around getting distracted in the mailbag. 

Barring unexpected travel difficulties — or me being murdered by a crazy fan — the anonymous mailbag should be good to go for the rest of the year. As always, you guys are the fuel for the anonymous mailbag. The rules are simple, you email me your questions, I promise to never publish your name. 

With that in mind, here we go. 

“I recently started seeing a guy I met on Tinder. He is quite a few years older than me, 15 to be exact (I’m 25), and recently separated. We had somewhat of a rocky start. I invited a guy friend over to my house for dinner one night and didn’t tell Tinder Guy about it. When I didn’t answer his call he drove past my house and saw another car in the driveway. He then proceeded to make several passes until my guy friend left. I was unaware of his stalking so when he called again that night I still didn’t say anything.

The next day he called me out on the lie and asked if I had slept with my guy friend after I had slept with him. I told him no, but he never really believed me. He talked to his friends about it and they all agreed, there was no way that my guy friend and I didn’t sleep together, especially since he had stayed until 1am. He did say that he could move past the issue, and start fresh, but he continued to bring it up over the next two months.

Fast forward to a week ago. He texts me saying that he needs to ask me a favor. And if I do what he asks then it could be really good for our relationship. I go over to his house and he proceeds to ask me to take a polygraph test. Yes, you read that right. After dating a guy for a total of 3 months, he asked me to take a polygraph test to prove my fidelity. He’s willing to pay $400 because he doesn’t believe what I’ve been telling him. At first I was shocked, but then I quickly came to the realization that if I go ahead and take the test, and pass, then it will be the ultimate fuck you.

So there I am, in a small room with a middle aged, bald southern man asking me questions about my past relationships, if I’ve had any sexual encounters with anyone other than Tinder Dad since we’ve been together, if I’m on any dating sites, if I still have feelings for the guy friend I invited over that night, etc.

The results are in…. I pass. With flying colors.

Tinder Dad looks almost disappointed. But he quickly changes to, well I was pretty sure you were telling the truth. He has roses waiting in the car and tries to fuck me when it’s over. And now we’re going to DC for the weekend.

So I have two questions. Do you think Tinder Dad believes I’ve been faithful? And even if he does, should I stay with someone who went to such great lengths because he couldn’t believe/trust me?”

Holy hell. 

If you even contemplate polygraph testing someone you met on Tinder, I think it’s clear you’re dating a crazy man. This is incredible. It’s like a real life “Meet the Parents” scenario. 

But as crazy as it might sound, I’m actually more troubled by him driving by your house and waiting until someone left aspect of things than I am the polygraph test. Why is he driving by your place unannounced after just a couple of months of dating? And, more importantly, how many other times has he been spying on you that he didn’t tell you about?

You shouldn’t just end this relationship, you should run away from it. 

But congrats on passing the polygraph test. 

“Last summer I stayed in my college town and lived with a few of guy friends in a house. A local bar has a deal where every Wednesday night you would buy a pitcher of beer for $5 and there were free refills all night. Being the degenerates we were, this become a weekly tradition. After a couple of successful Wednesday’s in a row with the ladies, I decided to make this a streak. I went 5 or 6 Wednesday’s in a row without striking out. However, in the third or fourth week, I had work early one Thursday morning and didn’t go out. However, a girl who went out to the bar came over later that night.

The legitimacy of the streak has been hotly debated between my friends and I, can I count the girl as part of my streak. I say yes, they say no. Thoughts?”

Was it a new girl or an old girl? If it was a new girl, the streak continues. If it was an old girl, the streak died. 

“You’re gay so you may not know too much about heterosexual sex, but people keep asking you anyway so here goes:

I’m a junior at (redacted Big East school) (not SEC, I know it sucks) and I’ve been dating this girl for almost 2 years. My question is 2-fold.

First, I know everyone says dating in college is a terrible idea, but it’s not that bad. Am I crazy for doing it?

Second, I think this girl might be the one. There’s only one problem, she’s hardcore Catholic pro-life and is absolutely against sex until marriage. It’s taken a shit ton of effort to get her to handjobs now with hopefully more to come. That being said, she and I agree on waiting till marriage for sex. My question then is, Is it bad to be a virgin in today’s society when everyone is into the hookup culture?”

Look, if there’s any ethos the anonymous mailbag tries to embrace it’s that two consenting adults can do whatever they want to do. That is, you guys can get dressed up in furry costumes and have sex or you can wait for marriage. So I don’t think this is a question of “bad.” If you believe that this girl could be the one you want to marry, go for it. It’s not really about what anyone else thinks, it’s about the two of you.

Here’s a bigger issue question for you — if your girlfriend is a strict Catholic — and waiting until marriage in this day and age is pretty strict — is she equally strict in other areas? For instance, are you never going to use birth control? I’d want to have those discussions too, just to see what I was getting myself into and make sure I agreed with her on all of this.  

Personally, I think getting married when you’re 22-ish is crazy. One reason that people who are virgins get married so young, I think, is because you’re both so eager to have sex that you’re willing to overlook other issues. Having sex is a small part of being married. (In fact, in today’s culture if sex is your goal, you should never get married.)  

But I got married pretty young — when I was 25 — and look how mature I am.  

Bottom line: Here’s what I think will happen, if you get married and are happily married you won’t think that much about the fun you could have had with other girls in college. If you don’t get married to your current girlfriend, you’ll spend the next couple of years bemoaning the stupidity of having a virgin girlfriend in college.

Good luck.  

“For my wedding, I did what all good grooms are supposed to do, which was shut the hell up and stay out of the way. However, I was surprised when my now wife asked me if there were any songs I wanted our DJ to play at the reception. I only had one request, which was American Trilogy by Elvis, which is Elvis’s version of Dixie mixed with a few other songs. Weird? Yes, but my two older brothers had it played at their receptions, and it was something that they both enjoyed singing drunkenly with their groomsmen. It looked like a great time, so I wanted the song as well. When I made the request, my wife’s mother-in-law shot it down with a hearty laugh. She said there was no way that we could play that because ‘there would be black people attending the wedding’. I reverted back to good groom mode and dropped it, because let’s face it, they were paying for the whole shebang and that meant that they could really play whatever they wanted. It still bothered me, though, so I asked my wife what the problem was. She said that her mother thought that any black people at our wedding would be offended because the songs refers to ‘the land of cotton’ and ‘Dixie Land’. Am I really the racist they painted me out to be, or is this a case of the Don’tOffendAnyones?”

Jesus Christ, your mother-in-law sounds awful. 

At least you don’t have to spend the rest of her life seeing her all the time. 

Good luck with that. 

And here’s the song for those of you — like me — who didn’t know it. 

You should have hired me to compromise. You could have played “Hypnotize,” by Notorious B.I.G on the front end of Elvis and “Gin and Juice” on the back end. Bang, problem solved.

Anyway, you’re totally racist too.  

“Clay, I am a huge fan of the anonymous mailbag. I am an administrator for a healthcare system & have a very busy schedule, with little free time to read. Being well-versed at time management skills, I began opening the anonymous mailbag, selecting the text-only option, highlighting all of the text ( a bit tricky) and selecting speak. My question is how many other anonymous mailbag viewers use Siri to read aloud the anonymous mailbag? If you haven’t tried it, it’s Gold. Hearing Siri’s voice discuss penis fear, group sex, and fucking Queen Latifah has me laughing like a prepuberty school boy. Consider this more of a guide for ways to enjoy the Anonymous Mailbag (works for all your other articles too).”

I’d like to say that I’m surprised anonymous mailbag readers have found a way to have someone else read the anonymous mailbag to them, but, nope, I’m not surprised.

Lots can happen when you take a week off from the anonymous mailbag. 

If you doubt that, read these two emails:

“A recent new reader here (it all started with your bitching of the speed traps in Alabama it was hilarious), anyway your anonymous mailbag is my favorite legal thing on the internet now. My predicament is pretty simple, I’m sure married men around the world are in the same boat. I’m a newlywed having been married this past November, I’m young (22) and in love. My wife is 22 as well. We met in high school and have been together 5 years now. When we first got together she was in good shape, not big by any means, but not so skinny that she looked like a flag pole either. She still isn’t “big” but her legs have gotten bigger and her stomach has more fat now than I would like (she’s only 5’4). She’s in good enough shape for a bikini still but women, IMO, should be in their prime at 22. She should be in the best shape of her life, instead she’s not and to top it all off she wants a kid (which obviously will put more weight on her). How do I tell her how I feel without pissing her off? Should I talk about it with a mutual friend (girl) and ask her to approach it or have her recommend she work out? She won’t go to the gym with me, at all. I’m at a loss here….. What would you do? Maybe ask your cover-up you call a wife how she would prefer for this conversation to go down….”

A week later the following email arrives. 

UPDATE: SHE’S PREGNANT! Man I feel like an asshole now hahaha

What a lucky woman. 

Send your anonymous mailbag questions to, full anonymity guaranteed. 

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.