Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to distract all of you from work.

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

Here we go:

“Got a friend who has turned into one of ‘those people.’ He always, without fail, will turn every conversation into politics. It’s pretty exhausting. He’s a Republican voter, and so another friend and I decided to get him for April Fool’s. We signed his email up for numerous newsletters, from the DNC to AOC to Ilhan Omar and the Impeach Trump newsletter. Several of these newsletters have hit and his reactions have been great. He does not suspect that it’s been any of us (see pictures) and thinks he’s been hacked. 

We’re thinking the next step could be order him an AOC shirt and deliver it to his house with a handwritten note from “AOC” thanking him for his support and his donation. Or, do you think we should just leave it as is?”
I love this prank, regardless of the politics involved.
I’d actually say you take it to another level beyond this — in the handwritten note from AOC thanking him for his donation, you have her say she’s going to be attending a fundraiser in his city and that she’d love for him to introduce her based on the generous campaign contribution he made and because she especially respects his acknowledgment of his white privilege and thinks her audience would too.
Chances are he’ll flip out and try to contact AOC’s office and I love the idea of one of her aides trying to figure out what’s going on here as well.
Or someone in the media ending up covering this as a legit story.
Either way you guys win and can claim you had nothing to do with it.
Great prank.
“I’m your age with three kids under the age of six, both my wife and I work full time (doing well financially) so as you know family time can be limited. Last year to get an hour back with the kids I outsourced lawn mowing activity to my neighbors 15 year old son and he sucks. He misses spots and edges all over the place, if there’s a big stick in the yard or toy instead of moving it he mows around it….feels like he’s just trying to get through the job as quickly as possible, get his $25 and get the hell out of there. Last year he somehow lost the gas cap and never noticed (I bought a couple of gas caps as I could see this happening again).
We live in a nice neighborhood and I’m not really concerned with how our yard looks compared to other houses but get more irritated at the lack of focus along with the patches sticking out that he missed. Cutting grass isn’t that hard, just follow the lines! I’m tempted to start doing it myself but don’t want to start a war with my neighbor, thoughts on how to kindly tell the kid to get his head out of his ass?”
Tell him the next time he comes over that you’ll pay him when he finishes the job.
When he says he’s finished walk outside and check out his work. If you notice something he missed, point it out and ask that he do that before you pay him.
That seems completely fair.
Honestly, you’re doing the kid a favor. Right now the lesson he’s getting is doing shoddy work pays just as well as doing good work. Anyone who has to work in the real world knows that isn’t remotely true. So why not start teaching him that lesson now?
I’d imagine that far from starting a neighborhood war his parents would probably respect you for doing this, since, and I’m guessing here, if they have him mowing your yard for $25 they’re probably trying to instill a decent work ethic in him.
The nicer the neighborhood the tougher this is to pull off because rich kids already have most of their basic needs met and can often be lazy as a result. This is something I worry about with my own kids — we have way more money now than my family ever did so how do I make sure my kids have drive, work hard, and don’t take for granted their advantages?
It’s probably the thing I worry about with my kids the most.
Now this is definitely a first world problem, but it’s something I think lots of parents who have more than they grew up with worry about.
You can help out by insisting this kid do good work for the money you’re paying him. I don’t think there’s any way his parents will be upset with you for this and if they are, just pick another kid in the neighborhood who would be happy to earn the money.

“I’ve been out with a woman three times and she hasn’t paid for any of it. We’re both young professionals (I’m an attorney and she’s a financial analyst) in our 20s. She makes more money than I do, and offered to pay for drinks on the first date which I said it’s fine I got it. The second date she was in the bathroom when the check came (not sure if it was on purpose or not). The third time I let it sit there and when she didn’t even look at the check I decided it’s apparent that I’m paying. And because its relevant, I’m not getting laid either.

Am I being unreasonable in expecting her to at least give me an offer to pay? Like I said, she makes more money than I do, but just because I asked her out does that mean I have the obligation to pay every time?”

She’s a financial analyst who has made the calculated decision that you should pay for the privilege of spending time with her.

Even in an age of #metoo and total equality, a huge percentage of women still believe that men should pay for all dates.

So the next time the check arrives at dinner, refuse to pay. Sit there as long as necessary until she offers. If she won’t offer then inform her that as a huge proponent of the sexes being equal you believe a couple should split all dating costs and you’ve noticed that she hasn’t paid for anything so far.

She knows she hasn’t paid — again, she’s a financial analyst, money isn’t sneaking up on her — so she can’t play dumb here.

I have no idea how she’ll respond — she might like the fact that you stood up to her and showed some balls — or she might hate you and stop returning your texts. But either way, so what?

Plus, let’s be honest, if you really liked her that much you wouldn’t be complaining about having to pay for everything.

It’s not just that you’re paying for everything, it’s that you think she isn’t worth it.

So you might as well move on.

“I recently got engaged and moved in with my girlfriend. Adjusting to this new lifestyle has been a lot easier than I expected with one catch- I feel like I have to pull a Tiger Woods like Masters comeback to be able to do what I want. I’m not saying come home and play video games for 8 hours after work or go to Vegas with the boys. I’m talking about 1-2 hours a day where I can do something I like.

Another element of urgency is that I start law school in the Fall and I know my time for fun will disappear instantly. I’m pretty active helping around the house -on a daily basis, so I’m not putting everything on her. As I sit in the living room with my DBAP shirt I’m beyond confused. What would you do in this situation and any other tips on the matter?”

If you are already unable to do what you like for even a couple of hours a day now that you live with your girlfriend you need to move out as soon as possible.

I’m not even kidding.

I’m a big proponent of living together before you get married, but if you’re single and your girlfriend is already sucking up all of your free time the rest of your life with her is going to be miserable.

Escape while you can.

That’s especially the case if you’re soon to be a first year law student because you’re about to enter intellectual boot camp. This means you’ll have limited free time and the free time you do have you’ll probably want to spend being able to cut really loose.

I know there were several married people in my law school classes, but I can’t imagine doing law school married because it would have cut out 90% of the fun of being in school with your classmates and all that would have been left was the grind, which is substantial.

So I think it’s incredibly important for you to create some space for yourself while you can.

Good luck doing it while you still can.

“I’m early 30s working in a service based department for about 3 years. There’s about 15 in our department, but our company has about 6,000 across the board.

I love what I do and who I work with, but myself and others don’t feel like there’s good leadership in our department. One guy abuses the lax schedule we have in place- he will not come in at all for an entire day, but doesn’t take any PTO on his timesheet- and the manager doesn’t call him on his bullshit. And that’s a weekly occurrence. On top of that, he’s lazy and his work reflects that constantly. People are unhappy about it, but nothing happens. 

Not to mention the fact that we are about to move from all having offices to all being in a cubicle farm in a few months. 

So….we have an anonymous ‘employee of the month’ type suggestion box in the hallway. You write in someone’s name and why they deserve it, etc. 

My question is- would it be a good idea to anonymously write on this submission our displeasure with our current environment to really voice our opinions? Would it even be worth it? Like I said, we all get along, but this one guy ruins a lot of people’s days with his abuse of the system.”

Yes, I think this is a good idea.  

You didn’t mention it, but I’d think not only is this guy taking advantage of a weak boss, but he’s also probably making all of you have to work harder to keep up with his laziness.

So go ahead and put him anonymously on blast and hope your company is intelligent enough to handle his behavior.

If they aren’t, I’d start looking for another job. Any company run this poorly, unless it’s the government, will eventually face severe issues.

“My girlfriend’s brother is graduating from college in the next few weeks. Her parents are divorced and she is worried about how her Mom will behave around her Dad’s girlfriend who is flying in to attend the graduation too. They have been divorced for 15+ years so it isn’t like the divorce is a fresh wound for their family, but the Mom acts erratically because she is an alcoholic. If she even has a sip of booze she turns into a hot mess.
I want to be supportive of my girlfriend but have no idea how to help in this situation. What say you, King Solomon of the Internet?”
My best advice for family drama that doesn’t involve you: stay out of it.
Just listen to your girlfriend complain, express sympathy, and MAKE NO EFFORTS TO SOLVE THE PROBLEM.
It’s tempting to try to solve all problems, but if you give advice she doesn’t like then guess what happens — she’s already stressed and angry and she going to decide to make you the problem.
You want to avoid taking on the shrapnel of her family’s relationship explosions so, again, you just listen to her and express your sympathy and avoid making statements beyond that.
Whatever you do, don’t pick a side between the dad and the mom. If you end up with this girl long term then the last thing you want is one of her parents hating you because you somehow got drawn into their drama.
The only benefit to you is this: other people’s family drama can be pretty entertaining. Especially at an otherwise boring event like a college graduation.
So enjoy the rubber necking.
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.