Anonymous Mailbag

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Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

Last week I got a Twitter request from one of our female readers suggesting that I not always use the Charlotte McKinney in a bathing suit picture as the cover image of the anonymous mailbag. Specifically, she requested that I put up a picture of Kliff Kingsbury in his bathing suit every other week for the female readers. So I decided to create our own special image for the anonymous mailbag. Voila, it’s perfect. You can assume that every woman writing a question looks like Charlotte and that every man looks like Kliff. 

Now that our weekly image is set, I can’t impress upon you guys enough how fabulous your questions for the anonymous mailbag are. I mean, truly spectacular. I wade through all the submissions every week and try and pick the best ones. But the success of the anonymous mailbag is totally in your hands. We’ve got tens of thousands reading this thing weekly now, but we need y’all to keep sending in good questions. That’s the lifeblood of the mailbag.  

Anonymity is totally guaranteed. You can email me at

Here we go. 

“I’m writing in for my friend because I live vicariously through her dating life. (I’m married with three kids). This has to go in the anonymous mailbag because there’s no telling if the latest guy is a reader. (If he’s not, she probably shouldn’t pursue him further.) As most females would do in this situation, we’ve dissected every minute of her Friday night date, but none of us can figure out what the hell is going on with this guy. They’ve been out a few times, and he pays every time. Lots of flirty texts and snaps (I’m too old to know what the heck that is…), but nothing physical beyond a hug has occurred.

Fast forward to Friday, they go out to dinner within walking distance of her place (all part of the plan to move things to the next level). They both end up drinking a decent amount and head back to her place. She can tell that he’s stalling his departure because he has multiple glasses of water and is making no move to leave. She finally asks if he wants to stay the night. He quickly agrees and they head upstairs. He strips down to his underwear and hops in her bed (guest room and couch are both available). She goes to the bathroom to freshen up and get ready for the big night. She gets in bed, and then….NOTHING. Casual chatting and then they both fall asleep.

Is he not interested? If not, why did he sleep in her bed almost naked? Could this be whisky dick? (Is that real?) If it is why not at least make out? What man doesn’t at least try to get some? I asked her if it was possible that they somehow got married since sleeping next to someone without touching is typical married people behavior. Please dive into the male mind and let us know what this guy is thinking.

PS: I already explained to her that the correct move would have been to strip down and tell him she only sleeps in the nude. There would be no question if he was interested, and we wouldn’t need your help. Kids today….”

I understand why your friend didn’t want to go any further — asking him if he wanted to stay the night and letting him stay in her bed was a double bold move that basically announced she was fine with hooking up with him — but I’m at a loss as to why this guy didn’t make any moves at all. Moreover, not only did he do nothing all night, he also passed up on the guaranteed re-hook up in the morning, which is the best thing about sleeping over with someone new. So he really passed on hooking up with her twice.  

Short of actually taking total control of things and initiating the make out herself — which is always an option but she probably didn’t want to do because she’d already invited him to her bed and let him sleep over — I don’t know what else she could do. Either this guy is a virgin or he’s incredibly awkward and has the lowest sexual self confidence on earth. I mean, this has to be awkward for him too, right? He has to know it’s not normal to sleep in bed next to a girl he’s dating and not even attempt anything.  

Here’s what I would suggest, the next time they go out — assuming she still wants to go out with him again — she needs to bring it up. (She could also bring it up via text. It’s less awkward this way and you say they have a flirtatious texting relationship, but I would encourage the face-to-face question because it forces him to answer without having time to think, making honesty more likely). Have a couple of drinks and then say, “Look, you slept in my bed and didn’t even try to hook up with me. What’s up with that?”

She’ll have her answer.  

(By the way, sources close to me report that whiskey dick is definitely real.) 

“Several mailbags have had people showcasing their impressive hookup stories, so I wanted to balance the scales and ask a question I’m sure you’re more familiar with: disappointing hookups.

Backstory: about 7 months ago, I had a severe throat infection that hospitalized me for 4 days and required 2 surgeries to fix. I was sent home with enough prescriptions to start a small cartel: painkillers, steroids, antibiotics, anti-inflammatories, maybe 1 or 2 others. During the 3 weeks of recovery, I wasn’t allowed to drink. The pharmacist also mentioned “possible sexual side effects”, but she would have been more accurate to say “your dick will be in a coma.” It was weird how noticeably non-responsive my genitals were to everything. Not even a hint of morning wood.

Flash forward 3 weeks, no more meds, clean bill of health – time to party. Go out with some friends, meet a cute girl, we hit it off, and end up back at my place. I can tell while we’re making out that something is still a little off, but I figure it can’t be that bad. It was. I lasted maybe 30 seconds, and it was still even less impressive than it sounds. I was visibly embarrassed, and placed the blame on all the medication. She smiled politely, but clearly didn’t believe me. I briefly thought about proving it with the hospital and pharmacy documents, but realized that would probably come across desperate and weird, even if I was technically correct. Knowing we didn’t have any mutual friends and that I would likely never see her again, I cut my losses and accepted it as we watched Netflix until her cab came.

Knowing you’ve disappointed your fair share of men and women in bed, how should I have handled this? How should guys in general deal with poor performance, whether there is a reason or not? And how does that approach differ from one-night stand to a relationship to marriage? Thanks in advance for your wisdom.”

Maybe I’m an idiot, but why couldn’t you hook up again after the premature performance? Or keep hooking up while you waited to recover? That would certainly be better than watching Netflix, right? (What did you watch on Netflix, by the way? Like a random episode of a series? “Sorry about that thirty seconds of awful sex. Let me make it up to you by putting on season two, episode three of “House of Cards.” How did you pick what to watch? It’s not that easy to pick a show on Netflix. That takes time. Somehow watching Netflix together is so much more awkward than just putting on a regular television show). 

Also, am I the only person who immediately thinks about the first time Ross and Rachel hooked up on “Friends” and he had a juice box that popped open? What a great scene that was. 

Anyway, I love that you immediately placed the blame on all the medications. I don’t blame you for wanting to point out that this was a sexual aberration, but even if it’s a lie, I think you go with, “I’m sorry, you are just really hot and I was so excited to hook up with you that I couldn’t contain myself.”

Then you hook up again after you recover.

Or you watch Netflix and pray that this girl doesn’t tell all of her friends that you lasted thirty seconds with her.

Which she will.

Good luck.  

(If this was a relationship or a marriage, this is a non-issue because you aren’t being judged entirely based on one sexual encounter. This is the sports equivalent of tripping on your forty yard dash at the combine. That’s it, you’re screwed).

“My friend recently hooked up with someone he met on Tinder. My friend got a blow job and ended up finishing a little sooner than he wanted. The woman apparently still wanted sex and said, “I still want this to happen, let me go grab a toy from my car and then I’ll be back.” Is this the best way possible for a woman to leave if someone finishes too early? Or is it possible this woman had some crazy emergency? Or what I think might be even better, she got to the car and thought, “You know, this guy probably wouldn’t let me stick this up his ass.”

What are your thoughts?”

I think this girl gave a guy she met on Tinder a blow job and then thought, “I can’t believe I just gave a guy I met on Tinder a blow job. I used to dream about being Cinderella. Now I blow guys I met on Tinder. Fuck my life.”

And she suddenly just wanted to get as far away from that part of her life as was possible.

So she bailed.  

“My friends and I would like some advice from the smartest gay Muslim we know. A couple of my friends work in an office where it is essentially the Wild Wild West. There is no holding back on cursing, smoke breaks, and now sexual tension. There are two girls that work in the office that are always making sexual jokes to my two friends. This happens everyday. Grabbing dicks and putting tits in their face are not out of the norm. How normal is it for males to be sexually harassed in the work place? This obviously seems backwards. There have been talk among us that the girls might be attempting to get them in trouble if (and when) my friends decide to do come on to these girls. What should they do?”

This is going to surprise a ton of people, but back in my days practicing law I used to teach sexual harassment seminars. That is, I am as close to a legal expert in sexual harassment as is possible. As a result, I’ve advised lots of men and women on sexual harassment cases.

One thing that is pretty valuable is creating a written record of all the harassment so you can document it. It’s best to create that record with email because the date and time stamp provides notice of when it actually occurred. 

So I’d suggest that your buddy and his friend send emails back and forth every time an incident happens. Do it from their private accounts as opposed to their work accounts. Just describe what happened.  

It’s also possible that your friends are total losers and these girls want to sleep with them and are constantly talking with each other saying things like, “I don’t know what else I have to do to get him to ask me out.” And one of the girls was like, “Just grab his dick and put your tits in his face, he’ll have to get a clue then.”

Do your buddies have no interest in these girls? Remember, it’s only sexual harassment if it’s an unwanted sexual advance. That’s why I always encourage you to listen to the speeches that people give at weddings. If the guy pursues the girl, it’s always played off as really cute. The bridesmaid will be like, “I remember when (insert groom’s name here) called you for nine straight days to ask you out and showed up on the front porch with roses for three straight days to apologize when he (inevitably did something dumb early in the dating life).” Everybody oohs and aahs in the crowd over how sweet this is. Except, if it didn’t end well, it’s creepy stalker behavior.  

Regardless, I think the idea that they are trying to trap them in sexual harassment is pretty ludicrous. What do the women have to gain here? But if that’s a real concern the emails would protect them. Instead of just the guys getting fired for sexual harassment, everyone would get fired.

I’m also left wondering, who is the boss here? And what’s he doing all day that he manages to witness none of this? He’s like a WWE ref who misses all the cheap shots.   

“I’m about to enter the married life this coming summer. Now let me first say, I love my soon-to-be wife with all my heart, and I consider myself incredibly lucky to be getting to spend the rest of my life with her.  She has a great sense of humor and really can just be like one of the guys to hang out. That, and super hot.  

All that being said, a conversation came up last week that I had never even thought to be an issue until now.  I’m learning that when you begin to live with a woman, men will make Christopher Columbus-like discoveries about their woman even if they thought they knew everything about them.  If you’re reading this and you think that, you’re wrong.  The conversation was centered around having a TV in our bedroom.  I think this is a fantastic idea.  We can both just chill in bed together catching up on some Netflix or maybe catch a late night movie before we drift off to sleep.  

She, on the other hand, not so convinced of the idea.  I believe her quote was something along the lines of “I don’t want us to get done doing it then you flip on SportsCenter.”  Am I completely wrong for thinking this is a absolutely plausible scenario?  Get done having sex with my beautiful wife, then turn on the tube to see how the Titans screwed up their latest outing.  She says the bedroom “is just not the place for that” in relating to the TV.  Help me out here.  Should I just give in for some unseen benefit of no TV, or should I pursue this?”

The TV is not going to be the reason you have or don’t have sex. You won’t have sex because you’re married not because of the TV in your bedroom. 

Plus, I’m with your fiancee and anti TV in the bedroom because inevitably the person who likes watching TV at night falls asleep and the other person, who hates having the TV on, will wake up in the middle of the night with the TV still on and have to turn it off.

Having said that, we haven’t had a TV in our bedroom for the first seven years of marriage, but we just moved to a new house and the TV came with the house and was already on the wall in the bedroom. So I tried to watch the latest episode of “The Americans” one night from bed, but we also have a seven month old baby sleeping in a crib in our bedroom and he was terrified of the show. So I’m still anti-TV in the bedroom. 

Whether or not to have a television in the bedroom is pretty much a 50-50 issue that cuts across the sexes. 

Congrats, it’s the first of many intractable and totally unsolvable conflicts in your marital life. Just get used to it.

Send your anonymous mailbag questions to

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.