Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to arrive and destroy all work productivity across the country.

But before we do that, announcement time — we will be giving you details on Outkick the Weekend in Las Vegas very soon. There were be a limited number of spots available for our inaugural Outkick the Weekend, which will be this August in Las Vegas, and the only way to guarantee yourself a spot is to be an Outkick VIP — you will save money on the weekend by signing up for Outkick VIP and get the right of first refusal on the trip. 

The only other way to guarantee yourself a spot is to get a mortgage with the presenting sponsor of the anonymous mailbag, The Home Loan Expert. If you close a mortage, refi, or prequalify for a mortgage in the month of April you will get a free weekend in Las Vegas. But you have to reference me or Outkick when you contact those guys at this website.

Okay, on to the anonymous mailbag. (Send your questions to the anonymous mailbag, anonymity guaranteed, by emailing me at

Here we go:

“I am a middle aged married man, good job, with one kid.  Work a lot during the week and do CrossFit on the weekends.  I have been going to the same gym for a few years.  Some of us run a few miles after the workout but lately that crowd has dwindled and there are just two of us – myself and a woman 12 years older. She is 49 and I am 37. 

The post-workout running club has been exclusively us for about 2 months now.  Last weekend during our run I make a comment that I was a little rushed because I will have to drive home, shower, then drive all the way back across town to meet up with family and extended cousins for a brunch.  

Her house is close to where the restaurant is. She tells me her husband and 2 kids are out of town for his  aunt’s funeral (she is a nurse and had to work part of weekend), so I can shower at her house to save time if I want. I said thanks but passed because my clothes were at home and I had to change anyway. 

As to my question, is this lady trying to F me? We have never flirted before. Just do CrossFit and have friendly conversations. But inviting someone to shower at their place is a bold move. I have never been there before, and I get an invite to shower there when the husband and kids are out of town? It seemed like a genuine offer and was not accompanied by any “fuck me” eyes. I honestly don’t know and go back and forth on this.”

I think she’s trying to bang you without making it insanely obvious she’s trying to bang you. Granted, I’m not a woman, but I just find it impossible to believe a married woman makes this offer without intending something more.

Let’s just take a step back for a moment — is there any married man reading the anonymous mailbag right now, who if they were out of town with the kids and they came back to the house unexpectedly and found a strange man showering at their house would think, “Oh, I was just trying to save him time,” would be a valid excuse from their wife for how the guy ended up in the shower?

No way, right?

The same is definitely true if a strange woman is showering in your house. I’m not sure there’s a man alive who could spin this innocently. “Yeah, my running partner had to make brunch with her family so I told her my wife and family weren’t in the house, but that she could come over and shower to save her time.” I mean, come on, there’s no way.

I don’t think there’s a man alive who would be okay with this decision from his wife and I know there isn’t a wife alive who would be okay with this decision from her husband. And the wife has to know this too, right? Especially since she’s telling you her family is out of town as part of her offer. That, to me, makes her intentions pretty obvious. If you were truly trying to save time and use her shower, would you care if her family was also in the house?

She’s definitely trying to bang you, but she’s allowed enough plausible deniability with this offer that she isn’t just coming out and straight asking you to have sex with her.

I do wonder, however, what this process would have looked like if you’d actually taken her up on the offer. Does she just walk in while you’re showering? Does she call out and ask if you need help in there like in a porno movie? Does she just climb in with you and say she’s sweaty from the shower and wants to save water? It still seems like a big relationship jump to go from jogging to banging a guy in your shower. But what the hell do I know, I’m not a married woman.

“I’ve been sleeping with a guy for almost 6 months now and it has yet to lead to anything. I don’t want to look like a psycho and ask for more when I guess we are just friends with benefits. But do guys want more or just like to have their cake and eat it too? If I ask for more am I just asking for it all to end? Time to move on and find someone who wants to invest in something real? By the way, I’m mid 30’s and just feel like the games should be over. When do guys realize that they have a good woman in front of their face? Are they always looking for better? I mean, I’m pretty, stable, funny and I ALWAYS give him what he wants. (If you get my drift).”

First, if you’ve been sleeping with a guy for six months, I don’t know how you’d look like a psycho for wanting more than just casual sex without commitment. So there’s nothing wrong with having that conversation. But I also think you should prepare yourself for the fact that he has an ideal arrangement now. Most guys, and I’m just being honest here, would prefer to have no strings attached sex — leaving sex with other women as a possibility too — than have sex in a relationship.

You, clearly, are not happy with that arrangement continuing indefinitely which is why I think you should tell him that. But if you make that decision I think you need to be prepared for the fact that he may not want a serious relationship and things between you could change.

After this conversation one of three things will happen: 1. your relationship will be over 2. he will agree to enter a serious relationship with you or 3. he’ll think he doesn’t want a relationship with you and then miss you — and the sex — and eventually enter into a relationship.

Two of three options here are good. And even the relationship ending isn’t a bad option either because then you can find someone who does want to be in a relationship with you. As you say, you’re in your mid 30’s, why waste time with a guy who isn’t committing to you?

Given that you’ve been together for six months in this friends with benefits relationship, I think it’s unlikely you’re going to make him commit to the relationship by having no strings attached sex. In other words, I don’t think he’s suddenly going to confess his love to you and stop your current situation. He needs to know that friend with benefits sex isn’t an option going forward before he offers any commitment to you.

As a general rule, by the way, you can’t screw yourself into a relationship, girls. Being the cool girl who has sex and doesn’t expect anything in return is not a very successful way to snag a boyfriend. Withholding sex, while it may seem conservative and dowdy, is a much better way to get a relationship than giving up sex on the first date.

Casual sex is fine, but just know that casual sex makes a guy less likely to commit to you. (Also, there are so many guys reading the mailbag right now say who know this is completely true, but are furious with me for sharing this with girls. Don’t tell them that, Clay!)

“So I’m a 26 year old guy that teaches/coaches in a small Southern town, above average looks, and old money within my family (I could do what I do for free and still never have to worry financially). My issue is this: there are NO attractive/successful females anywhere around here. I’ve been on a couple dates, but they are just girls who never left this town, have a job that pays hourly, and just above average looks.

Needless to say, I lost interest fairly quick. While I was in college, I never had any problems getting girls for the occasional one night stand, as well as a serious girlfriend for over a year that was way out of my league. So I know I’m capable of attracting girls given the opportunity, the only thing is that I have a career that I love in a small town.

I’ve already had a couple flings with the “hot young single mom” (They were hard 9’s…probably 10’s back in their prime) but there’s no way in hell I’m dating them. I know I can always find a job in a big city, but I’d be leaving my team that has been top 10 in the state the past few years. Again, coaching and molding kids into adults is something I love doing.
Any advice you have is greatly appreciated!”
I’m not an expert on dating apps, but can’t you set a large mileage radius on those things so that you reach into a larger metropolitan area with more fertile dating candidates? You’re a high school boy’s coach, which is a pretty dependable, and frankly, hot job for a guy to have if you’re a single woman. Sure, you’re not going to get rich, but you’ve got the Coach Taylor hotness working for you which is a big turn on. Definite hot dad bonus points galore right here.
If I were you, I’d cast a wide net and try corralling girls who are tired of the regular bar scene and interested in dating a normal guy. As a general rule, guys go to crowded bars to hang out because they like going to crowded bars to hang out. Girls go to crowded bars to meet guys so they don’t have to go to crowded bars any more. (Put it this way, I haven’t met that many women who get married and still want to go out drinking in crowded bars all the time. Just about every guy I’ve ever met who gets married still want to go out drinking in crowded bars all the time.)
If you start meeting women your age on the dating apps then you can eventually travel into the city to hang out with these girls on weekends when you’re free.
If they like you — and you like them — then eventually you can start to introduce the parts of life in a small town that you find so attractive that you don’t want to leave behind.
But I wouldn’t make your small town lifestyle a big part of your story until you decide you want to get more serious with the girls you’re dating. Let them believe you live in the vicinity of the “big city” until then.
The other option I see for you is chasing down girls who went to your high school on Facebook that are around your age and you think might be open to living in your hometown again sometime.

“Hey Clay, wanted to get your point of view on whether or not this is weird.  

So, I work for a very large chemical company and the company has plants all around the world. We work 12 hour shifts going back and forth between days and nights and we’re all just blue-collar workers, with the exception of the day-shift/ office workers and management. Us shift workers, the majority of us being men but there are plenty of females too, have sort of an inside joke about how attractive females are and we always say “once you come through those gates, your standards drop to some degree.” 

Basically, inside the gates at work most men think certain females are total smokeshows while at the same time if we were to meet the same females outside the gates we most likely wouldn’t even give them a second glance. This got me thinking, do men at most workplaces think this way as well or is this just an example of “toxic masculinity.”

Every man reading this right now knows what woman he would have a child with at his work if the world was going to end tomorrow and you had to save the planet.

I mean, every single one.

One of my good buddies said he never enters an enclosed place with a woman — elevator, bus, subway, airplane — without thinking about who he’d sleep with first if the opportunity presented itself. That’s a funny line, but there’s a lot of truth to it too. I can still tell you every girl I’d pick to sleep with from just about every high school class I ever took. (Seriously, I used to sit in glass drafting girls like I was Jimmie Johnson running the Dallas Cowboys back in the day. My drafting goal was to maximize the number of hot girls I could sleep with without picking the same girl twice. So I’d legitimately sit there debating my sex picks to be named later in my head. “But if I take her in English then I don’t have her in gym class later and I might get stuck with…” I mean, seriously, I bet every guy has done something like this in high school and college).

Every guy reading this who has ever served in the military, especially if it happened overseas, can attest to the fact that women on Middle Eastern bases soar in attractiveness because there are no other options.

This is not an example of “toxic masculinity,” this is an example of biology. Although, increasingly, the far left is focused on trying to make men less like men and more like neutered beta losers. Which is fascinating because do you know who doesn’t want to sleep with neutered beta losers?


Anyway, no, you’re normal.

“A little background: I met a guy in September 2016 in a hotel bar. He’s cute, successful, and we totally hit it off. We end up exchanging phone numbers and making out a little bit in the elevator before parting ways. 
Then radio silence. March 2017: I get a phone call from the guy; he’s in a nearby city for work, and wants to fly me out the next day for the night and buy me dinner. I’m in my early 30s, so it’s not like I don’t know what’s going on here, but I’m like, what the hell, you only live once, I’m doing it for the story. 
It’s great; we have a fantastic time, enjoying good food and libations, laughing, talking all night, go back to his hotel…you get the idea. He drops me back off at the airport the next day, and he says he’ll call me. Radio silence. Again, I’m not thinking this is my future husband or anything, and I’m definitely not heartbroken; I’m the kind of girl who takes an experience like this for what it is and laughs about it with her friends.  
Here’s where my question comes in: this past week, I get a LinkedIn request from the guy! A year (almost to the day) since we saw/spoke to each other.  This is totally weird, right? Do I accept? Anticipating your question: I’m not looking for a round two. That’s totally what he’s doing, right?”
I’m not sure if he’s looking for round two, but it’s definitely sort of odd behavior. If he wanted round two, why wouldn’t he just call or text you again? So I think there is likely to be another explanation.
For instance, I never know how LinkedIn works, just that they used to spam people mercilessly until you signed up for their website. So is it possible he’s just hit the wrong button and a ton of his phone contacts were all simultaneously invited to connect with him? Or maybe he’s recently lost his job and he’s scrambling to find a new one and is using every possible avenue possible to find a new gig?
I don’t think he’d try and bang you through a LinkedIn message. Primarily because I’m on LinkedIn and I have no idea how the messaging works.
Also, and you may have checked into this, but is it possible he’s married? That would explain the infrequency of his communication. Further, did you ever have any contact with him after the hook ups or did you leave it entirely up to him in order to keep him thinking you’re cool?
Regardless, you have to accept his LinkedIn request. After all, you did bang him. Not accepting a guy you banged’s LinkedIn request is thoroughly unacceptable.
Send your 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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