Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

As always you can send your anonymous mailbag questions to, anonymity guaranteed.

Okay, here we go:

“I’m 57, proud dad to a 21-year-old son. And I discovered a problem last night.

First thing’s first. His mobile phone is somehow linked to my iTunes account. Every once in a while, I’ll get the occasional text from one of his friends. It’s annoying to me, because I’ve asked my son to figure it out, but he just shrugs his shoulders. 
The complicating factor? Any photos he receives via text goes to my iTunes photos. Don’t ask me how. I’d stop it if I could. 
Last night I was going through our photos. I spotted a photo of a girl I didn’t recognize. I’m guessing it’s my son’s new girlfriend. 
Clay, she is completely hot. Not stripper hot, but good-girl-gone-wild kind of hot. Hotter than a five dollar pistol on Saturday night. Blonde, well-groomed, a body to die for. I see the photo and think, “Way to go son.”
So I hold up the laptop to my wife and say, “Wow. Our son has outkicked his coverage.” My wife, a pretty fantastic woman herself, just rolls her eyes. 
Here’s the problem. The more I scroll through my photos, the more I see of her than I really should. We’re talking nude selfies that show off her amazing ass, perfectly toned skin, and stately, pert breasts that are—quite frankly—magnificent. 
These, too, I called to the attention of my wife. Because the last thing I want her to do is go through all our photos on iCloud and think those were meant for me. Purely defensive measure on my part. 
We do the right thing and delete all the dozens and dozens of unbelievably sexy photos of this girl in her early 20s. 
So what question do I have for you? Several:
1) Is it wrong for me, at my advanced age, to recognize my son’s nude girlfriend is hot beyond belief?
2) How do I tell my son that he’s got to figure out this issue with our phones basically playing Voldemort and Harry Potter without embarrassing him?
3) What exactly do I say to this majestic icon of womanhood if my son starts bringing her by the house? 
For God’s sake, don’t run this with my name attached.” 

First, I mean, your eyes work, as long as you have a pulse I’d expect you to know what an attractive woman looks like. It’s not like at 57 years old you suddenly become unaware of what an attractive woman looks like. You’ve been honing your ability to scope out hot women for 45 years now. You’d be just blatantly lying if you pretended you weren’t noticing that your son’s girlfriend was smoking hot.

Totally veteran move by you, by the way, to immediately share what you were seeing with your wife. That’s the kind of veteran move that decades of marriage has taught you — when the grenade is laying there on the ground you have to point out that you had nothing to do with the grenade and run like hell in the opposite direction.

You don’t slowly walk up and check and see if the grenade is active, you always assume the grenade is active when you’re married.

Second, this could have gone so much worse.  Leaving aside if your wife finds these photos and immediately suspects that you have a college-aged mistress which could have been a disaster for you, what if, for instance, your son is banging a totally unattractive woman and she’s sending him all sorts of grotesque nude photos and you found those? Or what if he’s in to something freaky, like transgender fat people orgies — not that there’s anything wrong with that — and you got those instead?

All things considered, I’d be really happy about these photos, and not just because you got to see a smoking hot college girl naked.


Because incredibly attractive college girls have lots of suitors. The fact that your son has managed to snag an incredibly desirable woman is, all things considered, a pretty strong sign that he’s not a total fuck up.

So how do you fix this problem? (Come on, do you really want to fix it at this point. Who knows what she might send him next?!)

But the fix seems relatively easy, you take your son to the Apple store with both your devices in tow and explain what’s happening. I don’t know how anything on the cloud works, but it’s pretty clear your devices are somehow synced. The Apple geniuses should be able to fix it relatively easily.

In the event this girl becomes a serious girlfriend — or potentially the mother of your grandchildren — you and your wife can’t ever mention that you’ve seen her naked. Unless and until you both come to know her really well and you are aware that she has the sense of humor to handle this story. This kind of thing can become really funny a decade from now after she has multiple kids.



But in the meantime no college girl wants to arrive to meet the parents and know they’ve seen her completely naked.

Finally, come on, you really didn’t save a single one of those photos?


“I’m 33, my wife is 27. We are happily married and have 3 kids, ages 8, 6, and 3. My wife is hot, but she has always been self conscious about having “small boobs.” I’ve always told her they were great boobs, which they are (perky, firm, large A / small B cup). Anyways, she’s been wanting implants for a long time.

The 3 kids don’t leave us with a ton of disposable income to use for this, so I told her if she saved up the money for the procedure, she could get them. Fast forward a couple of years, a global pandemic, and an economic stimulus from President Trump.

We have a few thousand dollars that we considered to be disposable. Our jobs and income have not been effected by the insanity. My wife started asking if we could use the money for an above ground swimming pool for our kids. While the pool wouldn’t be too costly itself, I know there would be additional expenses to consider (dirt work, deck, tree trimming, landscaping, and yearly upkeep), so I told her I’d rather her go ahead and get her boob job with the money. She took my offer without a second thought, and her savings combined with our stimulus money are plenty for the procedure. So my question is, am I a terrible dad for denying my kids a swimming pool in order to get their mom new boobs?” 

The funniest thing about this to me is the president’s stimulus dollars being used for boob jobs. You know Trump would love this.

How many people do you think are using some of this money to help pay for plastic surgery? It’s gotta be tens of thousands of people, doesn’t it? Maybe even hundreds of thousands. I mean, I understand that tens of millions of people are out of work, but lots of people kept their jobs too. For them this money, like for you guys, is just a nice bonus.

As for screwing your kids out of a pool, dads and moms need toys too. When they’re older this will be a really funny story to tell.

Plus, I’m not an expert on above ground pools, but are they really that great of deals? It seems like they just end up creating huge messes.

Plus, remember, when Clark Griswold was planning on building his family a new pool in Christmas Vacation, do you remember what he fantasized about? The girl from the perfume store swimming at his pool? What did she have? Perfect boobs!

You can put the pool in next year.

And this way you won’t have to buy floats for the wife.

“Do you think a girlfriend would be more upset if they caught their boyfriend jerking off to his ex, her sister, or her best friend?”

Easy call, the sister, it’s more disrespectful and hurtful. That feels much more personal.

Here’s the girlfriend’s anger ranking:

  1. Sister
  2. Best Friend
  3. Mom
  4. Ex girlfriend

You can see in my rankings that the closer the person is to your girlfriend the angrier she gets.

I’ve got her mom at number three here because it’s weirder than the first two, but also much less likely. (The popularity of step-mom and step-sister porn makes me terrified for the future of our country, by the way. Y’all are a bunch of perverts. So maybe it’s actually way more likely than I realize.)

Now I also think you have to factor in what he’s caught jerking off to. If it’s actual nude photos then he’s clearly in a relationship with the sister or the best friend and there’s much more to be concerned about. (If it’s the ex-girlfriend it’s probably older photos. Side note: I think just about every guy keeps nude photos of his ex-girlfriend’s somewhere.).

But what’s he using for stimulation here in the case of the sister and the best friend? (He’d have to be using something in order for her to “catch” him. Getting caught jerking off, by the way, is a rookie move in the first place.)

Her catching him has all sorts of comedic potential, but I’m betting that most of the time it would be Instagram that’s he using. The ‘Gram is responsible for more orgasms than anything this side of 1980’s and 1990’s Cinemax. If the boyfriend has the sister’s Instagram page up and he’s treating his body like an amusement park looking at her bikini pics, that’s hard to recover from. The smart jerk off play here would be to at least pick a bikini pick of the sisters together because then if you got caught you could argue you were looking at your girlfriend and actually jerking off to her.

Which is, as we all know, incredibly romantic.

Anyway, the entire business model of Instagram, it seems to me, is built on smoking hot girls posting almost nude photos. If sexy photos were removed from Instagram and you could only post like food and family photos the entire market value of the site would plummet by 95%.

“I’m wondering if I’m crazy.  I live about 3.5 hours driving distance from NYC. My wife is a medical provider and recently took a 3 week contract to work in a hospital there. I am lucky enough to work remotely and so I stayed home with our two kids aged 6 and 4.  We are both in our mid-thirties. Anyway, a few days before she came home she hit me with a gut punch. “No sex till I get tested and it comes back negative.” Honestly, I get it, and since I am a gentleman, I will just browse pornhub like I had the past 3 weeks anyway.  So my question is this…am I crazy in thinking that I would have had zero problem having sex with my wife before she got tested and knowing that she was basically swimming in Corona less than 24 hours earlier?  I can’t be the only one dealing with some version of this scenario.”

I think most young, healthy guys would take that risk if it was a one-off chance. Like imagine you have a hot nurse friend and she texts you she’s been really stressed out at her hospital job and she’s finally got Friday night off and she wants to come over and hang with you, but is worried she might have the coronavirus.

You know if she comes over it’s almost 100% sex guaranteed, but you might get the coronavirus.

I think most young, healthy guys would take that risk, especially if the nurse is hot enough.

Now the husband situation is a little bit different, you know you’re eventually going to sleep with your wife again so I’d be more inclined to wait this one out. Especially given that you have two kids to take care of as well. I just don’t think the risk/reward is worth it.

The bigger question to me is how much does she have to get paid to leave you with the two kids for three weeks and then have to quarantine for two more weeks once she gets back? That’s five weeks with both kids and no sex. If I have to teach the kids during this entire five week period, as well as be responsible for them all day long, I’m not even kidding, I don’t know what dollar figure I’d need to get paid to make that happen.

Leaving aside the danger to her, which is obviously a big part of the salary demands, I truly think I’d go insane trying to teach all three of my kids every day for five weeks. I’m not even kidding. Now maybe I’d feel differently if I had no other job, but the entire time my phone would be blowing up with news and people who need answers to questions and I’d be unable to stay on top of whatever the latest news is and none of my kids would be listening to my teaching anyway.

I mean, what does a nurse get paid for leaving her family for over a month like this to take a really dangerous job?

We’ve got pro athletes saying they aren’t willing to take the risk of playing a game and nurses are getting paid to drop into coronavirus hot zones.

Am I crazy to think it’s got to be at least $25k a week for most people to take this gig?

And even that seems low to me.

Anyway, I’d hold off on the sex here.

But props to your wife for having more balls than most pro athletes.

“I’m sure you’ve received a million mailbag questions on ‘will my wedding be canceled due to COVID-19.’ My question is more about whether it’s even worth having a wedding in 2020.

My fiancee and I have been planning a New Years Eve wedding (in a southern state that has had relatively COVID relaxed restrictions so far) for nearly 9 months now. We just want to throw a big party with all of our friends and family. Pre-Corona, we budgeted $30k for the wedding ($10k of which has already been spent in non-refundable deposits and whatnot), and planned to invite about ~200 guests. 
We can say pretty confidently that we’ll be ‘allowed’ to have a wedding in December, but I’m not sure what restrictions we may encounter. We’ve come to terms with the fact that grandparents and some older relatives will likely decide to skip the wedding, but what if the venue requires people to stay 6′ apart, prevents them from dancing, makes them wear masks, etc? If that’s the case, then we don’t want to spend $30k on a wedding. 
If the venue caps the capacity at 50-100 or so people, then do we cut the guest list to just family and bridal party (which is at least 80 people)? Having less people will decrease our costs, but that would mean cutting a lot of people that we really wanted to celebrate with.
We briefly discussed moving the wedding further out, but we don’t really like the idea either – If we’re not allowed to have people on a dance floor in December, are we really that confident that we’ll be able to do so in March? We could wait until December 2021, but we had discussed potentially being pregnant by then.  
At this point, my fiancee and I have decided that if we can’t have the wedding we want, we’d rather have a small 15 person wedding (just immediate family) and put the remaining $20k towards a new home. 
I need wisdom from the Gay Muslim. How likely do you think it is that we can have 200 person wedding where we and our guests can actually celebrate and dance? And perhaps most importantly, when do we need to make a go/no-go decision, and what should we consider?”
I’d put the $20k towards a new home and have a small wedding.
This seems like an easy call to me.
I’m not as confident as you are about a New Year’s Eve wedding either. And I’m certainly not that confident that the wedding venue, which will, I’m assuming, be mostly indoors because of it being colder, are going to allow you to have a traditional wedding by then. I think it’s likely they will still be implementing restrictions on seating, dancing, and social interaction. (I’m not giving my opinion about whether they should do this, I’m giving you my opinion about what I think they’ll be doing).
And, again, that’s if they let you do it at all.
I do, however, feel pretty good about people who are set to have weddings in July, August, September and early October in most of the country. The data on the coronavirus declining seems pretty solid as we head into the hottest summer months. So I think that 15 week summer window is viable with the obvious caveats about the rules being different — New York and California for example are likely to be far more restrictive than much of the South — depending on where your wedding is.
Since the cold and flu season typically gets underway in December in much of the country and accelerates through the holidays into January and February and March before it begins to subside, I’d be nervous about a New Year’s Eve date. The coronavirus seems to be following the same trend line as most cold and flu viruses would would mean the winter, when your wedding is presently scheduled, is likely to be more of an issue than the summer and early fall would be.
This is also why I think it’s smart for colleges and schools to consider coming back to school earlier than normal and taking a decent break in the winter before they come back for spring.
That’s why I’d put the money into a house if I were you.
Then throw a big, awesome party at the house for all the people you didn’t get to see at your wedding in the summer of 2021.
Good luck.
Thanks for reading and as always send your anonymous mailbag 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.