Anonymous Mailbag

It’s Wednesday — I know, I know, a day late because of the holiday and the college football playoff games on Monday night — and it’s time for the anonymous mailbag this week.

Send your anonymous mailbag questions to, anonymity guaranteed.

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Okay, on to the mailbag.

“Over the past 15+ years of sleeping in the same bed with my wife, I opine that myself, as well as 99.9% of males, both hetero and otherwise, would love to be woken up at night, in the morning, practically whenever, with either oral sex or a hand-job. Unfortunately it hasn’t ever happened to me and I doubt it has happened to most men reading this either. 
I tell my wife all that time that on those nights where she couldn’t sleep or those mornings that she wakes super early that she should just get the party rolling.  
I totally understand that from the women’s point of view, she doesn’t want to be woken up from a dead sleep for sex, but for men I argue that’s not the case. My wife argues that 1) she would feel guilty for waking me when I am sleeping peacefully and 2) she says that she is terrified that I may issue another female’s name in my sleep. 
I respond with  1) don’t worry about the sleep and 2)roll the dice, worst case it will be her mom’s name
I have even tried to make it a challenge for her by suggesting that she try to complete the job without fully waking me, but alas no luck to date.”
I would love to know the percentage of married men that have ever woken up to an unsolicited blow job in the middle of the night? Five percent? Lower? I think it’s a tiny percentage.
That’s because most married women don’t want to suck a dick when a man’s awake, the last thing they want to do is suck a dick while he’s sleeping. Never wake a sleeping baby or a sleeping husband.
Although, what an outrageously bold play it would be for a wife to just lie about this.
What if you woke up in the morning and your wife was like, “Hey, you were really sleeping last night, but I hope you don’t mind that I got really turned on in the middle of the night and just had to suck your dick and swallow it all.” Slowly rub his arm as he wakes up and sits there dazed, “Do you not remember it, hunny?”
Then pout a bit.
Wouldn’t every husband have to lie and pretend that he remembered? And what evidence is there to prove your wife is lying? It’s the perfect crime if she claims to have swallowed. There’s zero evidence.
Honestly, if you’re a woman and you read the anonymous mailbag and your husband or boyfriend doesn’t — assuming there’s anyone in this camp — try this and see how he responds. I guarantee he tells you that you were amazing and it was awesome. Because he’s going to be terrified to say otherwise. You might be able to keep this ruse going for years. Especially if you only claimed to be doing it a couple of times a year.
Hell, he might even buy you a more expensive car. You can pull him aside as you’re car shopping. “Honey, think about all those times I sucked your dick in the middle of the night while you were sleeping just because I love you so much. Don’t you love me too?”
It’s an amazing play.

As for what percentage of men would be okay being woken up with a blow job? It’s 100%.

“I was recently at a wedding and was introduced to an attractive female.  Unbeknownst to the mutual friend who introduced both of us, said female and I already knew each other. 

From high school. 

Only I’m a 27 year old high school teacher and the girl is 19 now, almost 20 and was a student at my high school. Now I never had her in my class, but she is really good looking. 

The wedding was semi-awkward for a bit, and then I ran into her again over the holidays – at a Christmas party – where we talked for quite a while. Legally I know everything checks out, but am I crossing a moral gray area here if I take her out? I have some other options, so not totally hanging my hat here, but the thought has crossed my mind. I’m conflicted on this one, stigmas and reputations go a long way in small town USA.” 

I’m assuming the girl didn’t go to college?

Because I can’t imagine that many 19 or 20 year old girls want to date their former teachers while they’re in college. (Or anyone else who is 27 years old and has a real job for that matter). But if she lives in a small town and is already doing a job of some sort or the other then I think this is way more defensible. You grow up much faster when you have to get a real job at 18 than you do if you go to college and continue on to grad school.

Plus, I just don’t really see the downside here.

Think of it this way, if she’s twenty and you’re 27, what’s the worst thing that people in your town can say, that you were hooking up while she was in high school and you were 24 or 25 and she was 17 or 18? If there’s no evidence of that happening, what’s the risk here for you?

After all, if you live in a small town and you’re 27 aren’t you eventually going to have to date someone who graduated from your high school? Is it better if you’re dating a 24 year old former student who went to your high school as opposed to one who is twenty? I guess so. But does it really matter that much? I don’t think so.

So if you’d like to date her, go for it.

By the way, I’m always amazed that people get surprised when young teachers get mixed up with students they’re teaching. Are we really surprised that a 22 year old guy or girl in his or her first year of teaching would be attracted to an 18 year old guy or girl who was a senior at that teacher’s high school? If that attraction happens on a college campus it’s completely normal.

Now I get it, there’s a power dynamic at play here when it’s a teacher and a student and it’s an unequal relationship and it shouldn’t be permitted, but I also understand that very impermissiveness makes the attraction feel even stronger and more illicit.

Hell, there’s a reason so much teacher student porn exists, because it’s sexy on both sides.

I knew teachers who hooked up with students when I was in high school and I bet just about every person reading this did too.

It shouldn’t happen, but it certainly does.

Especially because, and let’s just be honest here, 17 year old girls and 22 year old girls are virtually indistinguishable now. Hell, go to the beach this summer and try to figure out whether a girl is with her hot mom or an older friend. Everyone wears the same skimpy bathing suits.

Try and figure out which one is the teenage babysitter and which one is the young mom.

Good luck.

Anyway, my bet is these teacher and students relationships are happening even more often now because kids all have their own phones and teachers all have their own social media accounts too. When I was a young kid I remember bumping into my elementary school teachers at the mall with my mom and being stunned that my teachers had lives outside of school.

“Mrs. Hill goes to the mall too?!”

Even when I was a teenager it was incredibly rare to have any interaction with a teacher outside of school or sporting events. Now no hot teachers wanted to bang me in high school — I don’t think any hot teachers want to bang me now either, FYI — but there was no way they were going to be calling my house.

But nowadays everyone has social media accounts so the interaction can start out innocent and move to inappropriate with no one else monitoring the interaction. So I’m sure there are more opportunities for these inappropriate relationships to happen than ever before and I’m sure they are.

It’s just a total minefield out there, good luck to all of you.

But go ahead and date the hot student.

“So I’m engaged to an awesome girl but something has come up that has me worried.. I’m headed to New Orleans next weekend for my buddy’s bachelor party and the topic of strip clubs came up with my fiancée. She believes that me visiting a strip club is grounds for calling off the engagement. Give the ring back, pack her shit, wedding is off, full on breakup. She was raised in a pretty strict baptist household but she’s never had a stance such as this on anything else. We go out regularly with friends and drink, have sex before marriage, etc. Now I’m not even that big of a fan of strip clubs, I think they’re a waste of money and an expensive pair of blue balls but now I almost want to go just out of spite. What says you the gay Muslim ruler of the Twitterverse?”

If she calls off the engagement because you went to a strip club then she doesn’t like you that much.


I think this is a fake threat. Women love to make fake, grand threats to make points and then they don’t follow through. Find me a woman who hasn’t screamed, “I AM NEVER (doing something that she immediately does again a week later) AGAIN. EVER!”

My wife used to do this more often and then when I’d call her on it she’d get mad.

I remember one time we went to Target and I stayed in the car to read because I’d rather stay in the car to read than go shop in most stores and she comes storming back to the car and yanks open the door and throws her bags in and she’s like, ” I AM NEVER SHOPPING AT TARGET AGAIN!”

And then she gives me some convoluted exchange of product story that I didn’t really pay attention to, but I said, “Stop, you’re going to go to Target again.”

And then she gets mad at me and she’s like, “Don’t tell me that I’m not going to Target again!”

“Okay, but you’re going to go to Target again.”

And before long she’s yelling at me for not believing that she’s going to go to Target again. Welcome to marriage, by the way. (Spoiler: she went to Target again)

This is all social media is, by the way, people claiming that they are never going to do things that they will immediately do again whenever it’s inconvenient for them.


Two days later, “Fuck, is the cab still not here? Really?”

“Okay, fuck it, let’s get an Uber.”

The lesson: boycotts only work if your product is shitty.

Anyway, back to your question, women spend their entire lives obsessing over getting engaged. Everyone knows you’re engaged to this girl because she told everyone she knew the minute she got engaged to you. There is no way she wants to say this sentence to them, “I told (insert fiance name here) that if he went to a strip club on a friend’s bachelor party the engagement was off. And then he went! So we’re done! Our engagement is over!”

Is there a single woman reading these two sentences right now who believes that’s a rational decision? Of course not. So she’s bluffing on that threat. You have to be able to use to your advantage that all women secretly fear that they’re crazy. And making this decision would move her perilously close to the outskirts of crazy town.

(Seriously, every reality show that’s insanely popular with women is really just an excuse to watch women crazier than they are to prove they aren’t actually crazy. Men are totally different in our reality viewing habits, men watch reality shows about men who are more of bad asses than we are. It’s fascinating to break down on a psychological level. That’s why if you’re a woman and you want to win a fight with a man call him a pussy and if you’re a man and you want to win a fight with a woman call her crazy. Bang, victory).

The bigger issue here with this strip club decree is this — your fiancee’s trying to control your behavior before you’re already married. This isn’t about the strip club, it’s about her being able to keep you from doing something that you would otherwise do to prove your devotion to her.

And, frankly, that’s not healthy.

Because right now it’s a strip club, but sometime soon it will be something else.

Maybe you think it’s worth it to give up those things that you would otherwise do for her or maybe you’ll do what a lot of guys do in situations like these and go to the strip club without telling her you ever went. (And lie to her if she asks if you went). But if you’re going to lie to her then you also have to tell all your buddies to lie for you and you might even have to worry about what they are posting on their social media accounts and what they tell their spouses and sooner or later you’ve got a mountain of lies you’ve built up to prevent your fiancee from knowing you did something that isn’t that big of a deal to begin with.

So I’d just tell her, fuck it, I’m going, you’re not going to like everything I do when we’re married either, call off the engagement if you want.

What I would tell all women about strip clubs is this, a group of guys on a bachelor party is much, much more likely to pick up girls out at a traditional bar than they are at a strip club. If you’re a woman worried about your boyfriend staying faithful on a bachelor party you should want your men in the strip club, the girls at the regular bars are a much bigger threat to you than the strippers are.

“So we just found out that my wife is pregnant. This is something we are excited about because we have been trying for a long time and it has finally happened. So my question is, what advice do you have? I figured you, being a father of three, have some sound, incredible advice for a guy like me at this point in my life.”

First, congrats.

Second, take a big trip after she makes it through the first trimester.

I tell this to everyone because I feel like so many couples having their first kid don’t do this because they end up focusing on too many other details.

But I don’t think you understand how much your life is about to change forever once you have a baby.

I certainly underrated it myself.

Now as you have more kids you will think back to your overreaction over your first kid and realize what total pussies you both were, but I don’t think you can underestimate the impact of one kid on a couple’s life. (And no, you fucking people with dogs who are “practicing with a dog,” have no goddamn clue what you’re in for either. Stop acting like assholes by pretending babies and dogs have anything in common at all.)

So get away on a Babymoon trip or whatever you want to call it.

We didn’t do it and I wish we had.

Because once you have that first kid it’s going to be a LONG ASS TIME before you are able to take a long trip and not worry about anything but yourselves again.

We had our first kid when I was 28. I’m 38 now and our youngest is three years old. That means from the ages of 28 to 53 I’m going to have kids under 18. (And this is assuming my wife doesn’t leave me. Because if she does leave me I’m going to end up married to a smoking hot gold digging 25 year old and I’ll have another three kids and be dead, potentially murdered by the pool boy my new wife is banging on the side, before my youngest kid gets to 18).

If my wife hasn’t left me and we make it to all of our kids being in college, that’s from the ages of 28 to 53 with kids 18 and under, that’s 25 years, a quarter century worth of time.

Now, you can certainly travel with your kids — and we do — or go on vacations without them — tough to pull off for more than a few days — but there is nothing like the freedom of two adults just being able to go anywhere they want and only being responsible for each other. So take at least a week to go somewhere really fun.

Send your anonymous mailbag questions to, anonymity guaranteed.

And go listen to the Hugh Freeze interview on Outkick from this morning if you haven’t already.

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.