Anonymous Mailbag

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Send your anonymous mailbag questions to, anonymity guaranteed.

Okay, here we go:

“I come to you seeking advice.  I have a friend of 10 years that is getting married in July.  Background, guy is 32 never married, no kids, and is marrying a 23 year old.  Now she is a touch immature and is an only child, but not bad looking and solid family. 

So my buddy wants to hit Vegas for his bachelor party, flights are cheap and I get free rooms at any Harrah’s property. 

I send a message to 3 other friends of his and acquaintances of mine, certainly not my friends. Anyway one pussy emails back and says: “Nice idea, if this were 10 years ago! I have a family now and I will not jeopardize that for a weekend of sin and debauchery in Vegas, additionally I will not be a part of denigrating the bride and groom’s relationship.” 

What a total bitch! I have yet to respond, but what is my play here, do I just let this guy be a pussy and snub his nose at us sinners, or do I call him out on it? WWCD…What would Clay Do?”

First, this sounds like it could be a really sarcastic email so I wouldn’t assume it’s intended to be serious.

You don’t know the guy so I’d call your buddy who is getting married and ask him if he thinks the email is serious.

If the email is serious this guy has major issues in his life and I’d just ignore him going forward. Anyone who is 32 years old and sending an email like this has either 1. been caught engaging in incredibly nefarious behavior by his wife and as a result his wife reads every email he sends and receives or 2. honestly, there is no other possibility here, he’s in marital prison.

If anything, the guy with the wife and kids should welcome the excuse to take a trip to Vegas more than anyone. Furthermore, if you’re willing to jeopardize your family and your wife in Vegas, you’re also willing to do it in an Applebee’s on a business trip to Muskegon.

The place doesn’t matter, it’s all about the mindset and the decision making.

I got married when I was 25 and I remember my brother–in-law, who was 34 then, was by far the most excited to go to the bachelor party. Why? Because he was married with a kid. Everyone else was around my age and a bachelor party, while fun and an excuse to drink more than usual, wasn’t that much different than what an ordinary weekend would have been like.

Assuming this email is real this guy has issues and he sucks, I’d just ignore him and plan the bachelor party with everyone else.

“A co-worker and I, both of whom are very conservative, straight, and married, were talking about a foster parent who we both agreed is very attractive. My co-worker replied that this foster parent’s husband is “very good looking as well.” I told him he was gay and he says he is comfortable with his sexuality and it’s not gay. I asked another guy in the office, who is also very conservative, straight, and married, who I thought for sure would say that it’s gay for a straight man to call another male attractive, however I was shocked to find out that he also does not think it is gay for a straight man to think another man is attractive. 
Since this talk, I have asked multiple other co-workers the same question (mostly female) and everyone else in an office of about 40-50 staff besides only about one and a few others that I asked outside of the office think that I’m weird thinking that it’s gay and borderline homophobic.
No matter the situation, I would never look at another man and think they are attractive. My wife even thinks it’s extremely weird for straight men to think this way. Apparently we are in the minority on this one. What’s normal behavior here?”
I think you might be gay, dude.
It’s perfectly normal for a straight man to be able to notice if another man is attractive or not. Or to be able to rate one man as better looking than another man. It has been my experience that the guys who are the most concerned with trivial issues like these are the ones who are actually the least confident in their heterosexuality.
In other words, the most homophobic people are often the ones who are actually gay.
George Clooney is better looking than Sam Cassell.
Being able to see this just means that my eyes work, it doesn’t mean I want to have sex with either dude. (Although, clearly, if you had to have sex with a guy you’d pick Clooney here.)

“My wife and I are trying to start a family. A couple months ago she was pregnant, but ended up losing the baby at the end of the first trimester. The miscarriage was a big blow for both of us, but we’re ready to start trying again. Both of us are mentally strong, now there are times that we need other people to talk to besides each other. Before the miscarriage we told our families and a few close friends. Our brothers, sisters and friends all kept this to themselves as we requested. Problem was her parents and my father told some people that we didn’t want knowing our situation. That led to the people they told trying to comfort us, which pissed both of us off.

My question for you is, if and when my wife gets pregnant again can we avoid telling the parents until after the first trimester or even wait until my wife is showing? I can certainly do this with my parents, problem would be with hers as they live in town and are nosy. My wife thinks they’d be devastated if they were out of the loop until later. Is it a dick move to keep them from knowing, or have they put themselves in this position due to the fact they didn’t keep quiet the first time? Anything I’m missing on this?”

Given the issues you’re having with miscarriages I would definitely not tell a single person about her being pregnant until the first trimester is complete.

And neither of you should feel guilty about this decision at all.

I totally understand sharing the news on the first pregnancy before the first trimester is complete because you were so excited to share your excitement with others that you didn’t think about the miscarriage possibility, but once you had the first miscarriage there is no way I’d share the news of a new pregnancy until the second one was well advanced.

Maybe, honestly, I wouldn’t say anything until she started to show.

If you keep the news quiet until then it’s not like her parents are going to be upset when they find out. They’ll be so excited about the grandchild coming that they won’t focus on when they knew, they’ll focus on the upcoming birth. And if, by chance, they are upset with your daughter for not telling them the moment she found out she was pregnant, that’s an issue for them, not her.

Good luck.

“Okay Clay, so one of our buddies who goes to a small college in an SEC state has been getting all sorts of signals from his teacher. We honestly think she wants him, but he denies it every time we bring it up. Signs include giving him her personal phone number, inviting him over to her house to receive extra tutoring at “any time,” and she also kept her hand on his leg for a while during one of their tutoring sessions. Now, are we just dumb and this is being a good teacher, or did he really miss out on an easy home run? (He showed us a picture and his teacher looked pretty good).”

If his teacher put her hand on his knee it’s certainly possible she wants to bang him. (She might also be touchy feely, the kind of teacher who likes to hug, and not thinking anything of it. It’s impossible to know for sure.)

But if she did want to bang him she might very well be afraid of making the first move because she has much more at stake here than he does. That is, she can lose her job, he can’t get kicked out of school for wanting to bang his hot teacher. If so, then every male student in history would be done with school.

What’s the worst thing that happens if you’re a student and you get shot down by your teacher? Maybe she gives you a bad grade? But I even think that’s unlikely because then the student could complain to her boss. I think your grade probably goes up here, honestly, because the teacher would be afraid to dock you anything at all.

Plus, your buddy gets an awesome story for the bar — the time he tried to hook up with his college teacher and failed. Trust me, that’s a great story for years ahead.

Tell him to #dbap

“My father-in-law is in terrible physical health (he’s in his sixties) and I don’t see him living that much longer. My mother-in-law isn’t in great health either, but nowhere near as bad as him. They haven’t handled their finances well, so when my father-in-law passes away, my mother-in-law won’t have money for a nursing home and will have to move in with one of her kids. My wife has 4 siblings but we are the only ones she could realistically stay with. My question is this: is it worth it to have her live with us instead of paying for her to be in a retirement home? She could help nanny our daughter and my wife could go back to work, but the thought of any relative permanently living with us is daunting.” 

I think a great deal of this decision has to do with the size of your home and whether you get along with your in-laws.

I’d be perfectly fine with any of my in-laws living in my house now, but I think it would have been overwhelming in our old house which was much smaller.

But if you have to choose between paying for your in-laws to live in an expensive assisted living facility or at your home, wouldn’t you prefer to have them at home? (That’s provided they don’t need substantial medical assistance and you can take care of them on your own).

That’s even more the case if they could help you with the kids.

“I recently quit my job to travel the world and volunteer abroad for a while (think anywhere from 7-12 months). This is completely self-funded, self-planned, and will be executed solo for the majority of the time save for when some friends join me for parts along the way. I’m single, no kids, but I am leaving a good job that I could potentially come back to. Part of me thinks I’m crazy. Part of me thinks anyone who has the freedom and ability to do something like this should go do it. What do you think?”
I think good for you.
Look, the unemployment rate in this country is 3.9% right now. If you don’t love your job and you’ve saved up enough money to take off a year and travel the world, go do it, you’ll be able to find a job when you come back pretty easily.
When you’re 58 years old and working your ass off do you think you’re going to think, “Man, I wish instead of working for the past 36 years I wish I’d worked for the past 35 years instead.
I’m going to turn forty this year and hitting that age will be the first time I actually think about retiring. Ages 25 to nearly forty have gone really fast for me and I can only imagine that ages 40 to 55 will go even faster.
And I think I might want to fully retire by 55.
At that point I’ll have worked for thirty years full time and my kids will all be in college or graduated from college.
I think I’d like to start traveling the world then while I’m still young enough to be in good health while I do it. Now maybe my opinion will change as I get closer to 55, but that’s the way I’m thinking right now.
I just don’t think there are that many people in their hospital beds staring down the final few days of their life who think, “You know what, I wish I’d spent more time working.”
I love my jobs now, but at some point I’ll have plenty of money and I’ll start valuing time more than I do money.
Once you have kids I think you often have to value money over time, honestly, which is unfortunate because that’s when you’d like to have the most time with them. But once those kids are off to college, you’ve done your job and I’m not sure what you’re working so hard for. If you love your job, that’s great, but otherwise you’ve already worked pretty hard, what are you hoping to accomplish from 55 to 65 that you haven’t already managed?
If you don’t have kids yet and you’ve saved up some money, boom, live it up.
Now I will say this, if you truly like your job and want to be good at it, you should bust your ass at work before you have kids. Because that’s your competitive advantage, when you have the time to outwork people. Once you have kids your free time will be comparatively limited. That’s why I always say to people, no matter how much time they work, if you don’t have kids, you aren’t really busy.
Because you’re just responsible for yourself.
Sure, you may work 12 or 14 hours a day, but in those other ten hours you don’t have to be responsible for anyone else at all. When you’re a parent with young kids you never really stop working all day long.
If you don’t have kids yet and you’re reading this, you might be rolling your eyes, but, trust me, one day you’ll realize how right I am.

“Got into a debate with my friends the other day on this… how many times a week is it reasonable/acceptable to jerk off?”

I think it depends on your age.

If you’re fifteen years old multiple times a day is perfectly normal. The same is true if you’re in college.

If you’re 65, not so much.

I’d say as a general rule an average of one time a day between the ages of 25 and 45 is perfectly normal and acceptable. That’s a twenty year period when a man’s prime reproductive pipes need to stay functional and primed.

From 45-55 you should probably dial it back to 2-3 times a week and once you’re older than 55 I’d hope you dial it back even more.

Think of it this way, what do you think your average 38 year old mom would find more shocking, walking in on her 14 year old son jerking off or walking in on her 73 year old dad treating his body like an amusement park? No doubt it’s the dad, right?

Hell, think about this in your own life, what would be weirder, walking in on your teenage brother jerking off or walking in in your dad?

No contest.

The dad is way more awkward.

Which is why as you age your jerk off frequency should decline accordingly.

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.