Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to cause all work productivity to cease across the country. (At least for those of you reading Outkick).
And in addition to being Tuesday it’s also the first day of spring and you know what that means, right? Competition to buy a home. No matter where you live the top houses in the top neighborhoods are insanely competitive to buy. And that’s why you need to make sure you are prequalified to buy a home through my crew at My guy Ryan Kelley will get you prequalified faster than any other mortgage company out there. So head to their website now and make sure you don’t miss out on the perfect house because you haven’t taken the time to get prequalified.
Okay, here we go with the anonymous mailbag. As always send your anonymous mailbag questions to
“I need you to help me on a debate I am currently in with my sister. She has been dating a new guy for 10 months. He is an avid recreational softball player (I would say beer league but like a bunch of weirdos none of them drink beer, this is serious competition). He plays in games three nights a week. He has his own custom bats, bat carrying case and glove. He says this is a “competitive” league, however, there are neither entry fees nor championships. This is recreational softball.
In addition to insisting that my sister go watch him at every game, for 95% of his games multiple family members attend. At most games, his Mom, Dad, Uncle, Aunt and even Grandma come to watch him play. He is 32. I think this is the strangest thing I have ever heard. Who brings Mom and Dad to a softball game? Mom and Dad are not just bystanders, either, they actively cheer for him during the game. My sister tries to defend it and says that it’s similar to watching a little kid in little league, however, he is a grown ass man. It is worth noting that his family is super close. They all live within a 1.5-mile radius and have multiple family dinners a week, so it’s not like they never see each other.
Is it normal for 32-year-old recreational softball league player to have Mom, Dad and Grandma come to softball games? I need to know if I am being overly critical or if this is strange behavior.”
Does he demand that they attend and get upset if they don’t come to his games or are they choosing to do it on their own?
I think this answers your question.
If he’s insistent that his parents and family members come watch him play and gets upset if they don’t come then it’s strange. Because, as you mentioned, he’s 32 years old. But if they are just choosing to come watch him play on their own, it could just be that the rest of the family is retired and they are still treating these games like he’s in high school or college. I think you’d agree it wouldn’t be weird if family members showed up to watch a high school or college games, right? (Showing up to watch intramural games in college would, I agree, be weird).
I mean, if you like sports and live close to the field, it’s pretty cheap entertainment, right?
I’m also getting the vibe from your question that this guy may be the only child or the baby of the family and it may be that his family is hanging on to his youth longer than they would other children. It’s possible that his mom just doesn’t want to let him go.
The other question I’d have is this, is anyone else showing up for these games? That is, are the other players having friends and family members come watch? Or does his contingent of supporters represent the entire fanship?
Plus, and I do think this is key, he’s single and never married. Until you’re married, especially if you’re a guy, your life isn’t that much different than when you were 22 or 25.
Put it this way, if I were still single, I have zero doubt my mom would come over to my house and clean or do laundry occasionally.
Zero doubt.
And I’m 38.
I think most moms stay connected to their sons in this way until we get married.
Finally, I know from my time in law firms that many law firms take summer softball league games very seriously. There were even some firms that would give out summer associate offers to really talented athletes to have a few ringers every year. And these were forty and, sometimes, fifty year old guys who made hundreds of thousands of dollars a year as lawyers yet fixated on the summer softball league team like it was the Yankees. So I don’t have issues with taking the games seriously even if they aren’t really that serious. This is a guy thing.
So if everything else about this guy is great, I wouldn’t get that worried about the family’s softball obsession. Odds are that if this guy and your sister got married that rooting interest would just transfer to their grandkid’s in little league baseball. And as a little league baseball coach, I can tell you that all of these family members coming to watch games is highly common.
Hell, my uncle and my dad have both come to watch our little league baseball team practice. And so have other granddads and family members.
So I think you need to find out the additional info before you can judge it completely.
“Can I be brings his own toilet paper to work guy? I have never had an issue in my life with toilet paper tearing me up. That being said the stuff at work sucks. I’m itchy and have chafed like crazy. So can I bring my own toilet paper to work? Or should I just suck it up?”
You can’t bring your own toilet paper to work because you have only two options then: a. you carry your own roll of toilet paper to and from the bathroom every time you go — which is insanely weird or b. you leave your own toilet paper roll there every time you go, which still means you have to carry it there and it’s still weird.
Neither of these are viable options.
I’d suggest wiping less aggressively.
Also, being less of a pussy.
Because if I were a boss and I had to choose between promoting two relatively even guys at work, one who brought his own toilet paper to work and the other who didn’t, I would pick the one who didn’t bring his own toilet paper to work.
“Next weekend, myself and a group of friends are heading to Cancun for a bachelor party. Which happens to fall right in the middle of college spring break.

We’re still deciding on our daily itineraries because the group is at a 50/50 split in terms of how to plan the weekend. Half of the crew (including the bachelor) wants to go full MTV Spring Break – bar crawls, wristbands, pool parties, wet t-shirt contests, nightclubs, etc. The other half suggests we stick to more traditional bachelor party activities during the day – fishing, golf, NCAA hoops – and maybe going out hard once or twice.

Normally this would be a no-brainer and “When in Rome” would apply. However, none of us are in college (or our early 20s) and the entire group is between 28-30 years old.

What’s protocol here? I’m leaning towards the MTV Spring Break side but can see the others’ viewpoint as well. Will a group of ~30 year old dudes look awkward trying to hang with the college crowd? Will a group of 30-year old dudes be able to last more than a day trying to hang with the college crowd? Curious to know your thoughts.”

I think you go out at night like you’re on spring break and spend the day doing normal bachelor party things. You can fish, you can golf, and you can watch basketball games. Then at night you hit up Senor Frog’s or wherever and see how that goes.
I think it’s much less weird for you guys to be out at night than it is to be at a foam party at noon.
What’s the worst case scenario here? You’re the old guys at spring break and a bunch of college kids you don’t know, and will probably never see again, make fun of you for being the old guys at spring break. Is that really that bad?
What’s the best case scenario here? Somehow hot college girls decide they want to bang some of you. Even if that’s a low probability occurrence — like a 16 seed beating a 1 seed — it’s at least remotely possible.
So why would you eliminate any option that could lead to hot college girls wanting to bang you?
As long as none of you have college aged sons or daughters that could end up at the same place — can you imagine how awkward it be if one of you had a hot daughter competing in the wet tshirt contest? — I see absolutely nothing to lose here.
Plus, when you’re 45 are you guys going to be sitting around thinking, “Man, I wished we’d played more golf and gone fishing more at that bachelor party 17 years ago!” You can literally do this for the rest of your life. At some point you age out of spring break, so take advantage of it while you can.
“So I have worked at this same company for 10 years. We have about 100 employees and it’s a great work environment. And let’s just be honest and say that we don’t have a lot of attractive females working here. Well awhile back we hired this beautiful woman. She is a 10 and it’s a no doubter. So being the single man that I am, I begin to talk to her not knowing much about her and then this talking leads to us hanging out and getting to know each other and hooking up.
After we hooked up a few times, she informs that she is married but wants what we have to continue because the marriage is gonna end soon. When she told me this it was around a month or so into it. We are currently on month 7 of whatever you want to call our relationship. Just wanted to get your thoughts on a plan of attack for me.”
Several questions factor in here: Does she have kids? Do you know the husband? Do other people at your place of employment know she is married or that you guys are hooking up? Does she currently live with her husband or are they separated? Is the divorce proceeding underway from a legal perspective?
All of these matter in terms of your decision going forward.
But in general my advice when it comes to married women is: don’t do it.
You’re a single guy, there are tons of single women you can chase after without having anything to worry about at all. Because at some point her husband may find out about you and decide he wants to kill you.
Do you want to deal with that risk? I wouldn’t.
So unless she’s actually initiated divorce proceedings, I’d steer clear of her. (Yes, even though she’s smoking hot.)
“Hey Clay, so my wife and I shower together from time to time as I’m sure most couples do. It usually happens in the morning cause the kids are still in bed and we have time to ourselves. Well I have always thought it was a normal thing to blow my nose in the shower and my wife gets totally disgusted.
Let me get this straight it’s not like I am taking her from behind and blowing my snot all over her back or anything like that I discreetly turn around and do it. It’s something about the steam in the shower that really loosens that shit up. I have tried blowing my nose before we get in but I always have to do it again once that steam hits me.  She told me again this morning how disgusting it was and I told her everyone does it and she said nobody does so I told her I was asking Clay so here we are oh wise one of the internet this is the question, to blow or not to blow?”
Is she more likely to have sex with you in the shower if you don’t blow your nose?
If so, I’d stop blowing my nose in the shower.
Having said that, I typically blow my nose in the shower too. (The thing I do in the shower that annoys my wife — and by the way, is there any man who complains about anything his naked wife does in the shower, I bet not — is I always fill my mouth up with water and then spit it out. I don’t really know why I do this, but I probably do it three or four times, at least, during every shower I take and sometimes I end up spitting out water near her.)
Anyway, worst case scenario, can you not blow your nose when you get outside the shower? Especially if it increases your odds of sex? That seems like a small price to pay. It’s not like you’re going to die of a stuffy nose.
“My wife and I have been married for 11 years.  Like many marriages, it’s been up-and-down and lately it’s been slightly rocky.  Now I have never cheated on her, and I don’t believe she has ever cheated on me either.  So the issue is this, a few days ago I noticed a woman’s jacket randomly placed in my garage.  I assumed someone left it there on accident as a few times over the last few weeks we have sold some things on Craigslist or a Facebook site — my wife sells the items online and I complete the transaction in person as she doesn’t feel comfortable with it.  Yesterday, she found the jacket and asked me about it.  I said I noticed it a few days ago but didn’t think anything of it.  I said maybe someone left it on accident, who knows.  She questions me of bringing someone else over when she’s not there and I truthfully deny that, rather angrily.  She messages back the people we have sold to and they all say its not their jacket either.  She grills me and now says trust is broken, blah blah.  I haven’t a clue as to whose jacket that is, and honestly I don’t care, someone probably left it there on accident.  Is there any way to get her to ease up or am I fucked even though I didn’t do anything?”
What else have you done?
Guys tend to focus on single events and believe that’s the reason why women are upset with them, but most women don’t work that way. They store up a series of slights — things that you or I, as guys, may not even notice — and then finally explode over an event that represents the proverbial straw that broke the camel’s back. And then we guys are left scrambling trying to resolve a single issue. And then the woman will say, “It’s not just that it’s….”
Whenever a woman says, “It’s not just that,” you know you’re really in trouble. (And women ALWAYS say, it’s not just that. Always.)
So I bet it’s not really the jacket, it’s that the jacket confirms a fear she’s already had, that you’re cheating on her. So what else have you done to make her immediately believe that a woman’s jacket at your house means you’re having an affair? It’s not about the jacket, it’s about the place she’s in where she assumes a jacket is evidence of infidelity on your part.
If you want to solve this issue, you need to find the solution to the issues that set her off when she saw the jacket. And to do that you have to think like a woman and work your way back to the root cause of her distrust and solve that. And we all know how good guys are at that, right?
Good luck.
“I am a junior at a big SEC school. I am in a good major, multiple job offers with fortune 500 companies. But I cannot seem to talk to girls or find a girlfriend at all. I am not in a frat or super social for that matter. How would you suggest I go about talking to women? What do I say to them when I first approach? I do not want to give off a creepy vibe or something. Any tips or tricks?”
First, you’re in luck, because women like to talk. And they especially like to talk when they don’t feel threatened or hit on. So I would suggest practicing talking to women in non-threatening places about things that have nothing to do with your own sexual interest.
That’s especially the case if the girls you are trying to talk to are good looking. Good looking girls literally get hit on all day long, every day of their lives. So the chances of you saying something so compelling that it knocks them off their feet — or out of their pants — when you walk up to them for the first time and they have no idea who you are is low.
Given the fact that you’re seeking advice on talking to girls you’ve probably also got confidence issues when it comes to talking to girls and that discomfort makes your conversation awkward and makes girls less interested in you. So like anything else, you need reps to get better. So work on talking to the girls in your classes in college. Listen to them, respond to their answers, become a good conversation partner. Those traits will help you no matter what you do for a living.
You’re a junior in college right now and about to be a senior. What I would tell you is to focus on getting a good job and being successful at that job and continue to talk to girls as equal conversational partners. If you can do that then something interesting will happen, women will start to find you.
Successful men are in high demand because more women than men graduate from college.
When girls are in college they are all trying to bang the same eight dudes who are really good looking and in the right frat.
But about the age of 25 a girl suddenly realizes that some of the frat stars she’s been banging are total losers.
And that’s when guys like you suddenly surge to the top of the draft board.
You just have to be prepared when your moment comes. So start preparing now by working on your conversational skills. Don’t focus on the sex, focus on listening to a girl and responding to what she’s saying. If you can do that, sex — and relationships — will follow.
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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