Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag. As always, send your anonymous mailbag questions to, anonymity guaranteed.
Speaking of Outkick VIP, there are 18 picks up in the VIP right now.
Yep, we’re going big this week. Get rich, kids.
And we’ve also done Outkick VIP events now in Atlanta, Nashville, St. Louis and Birmingham with many more to come.
Okay, here we go with the anonymous mailbag.
“So I am 28, well-traveled, college grad with a good job, funny, musician, in decent shape… and a virgin.  That must seem impossible in this day and age, and my excuses don’t really matter, but probably safe to say I keep my “standards” foolishly high so as to mask my crippling fear of rejection.  I have a relatively small but close social circle and have never been the type to mac on chicks at a bar/club (mostly because I’m the worst and most awkward small-talker on the planet).
Anyway, things are looking up since I started reading Outkick (there are no coincidences?).  I just started seeing this girl who is 23 and we’re really into each other and I dare say sex is imminent (famous last words).  I’m really not so worried about the act itself, but my question is whether or not I should mention before things start poppin’ off that I’m a virgin.  Meaning, would she find it sexy/endearing, or would it just add a layer of awkwardness and best to save that tidbit for afterwards?  I don’t know if she is a virgin or not, but I’m confident it’s no more than one or two guys for her.”
I’d keep quiet about being a virgin before you have sex with her for the first time.
She might find it endearing that she’s sleeping with a 28 year old virgin, but I think she’s more likely to find it awkward and potentially overwhelming. That’s because the best way to tell her why you’ve waited so long to have sex is because you’ve been waiting on the right girl — no one wants to sleep with someone who everyone else has rejected — but this also increases the pressure on the relationship a great deal.
Later on in the relationship, if it continues, you can confess to her and it will be a much more endearing detail. (Related: if you end up getting married, everything sounds cute at the wedding reception, no matter how stalkerish it sounds anywhere else. There’s a thin line between marriage and a stalking conviction. Think about wedding toasts, “We knew he was the right guy for (insert bride name here) when he wouldn’t take no for an answer and kept asking her out even though she told him she didn’t like him at all. He even showed up at her house for multiple days with flowers even though she wouldn’t answer the door!” Everybody grins and says awe in conjunction when that story is told at a wedding. If it’s told at a bail hearing everyone thinks the guy is a total creep. Seriously, if you compare wedding toasts with stalking reports, the lines are almost identical. The difference? The ending.)
You’re also 28 and she’s 23, which probably means that even if it isn’t true she thinks of you as worldly and more mature than her and that’s probably a part of her attraction to you. That’s a big difference in age and life experience. When you’re 68 and 63 the difference is insubstantial, but if she’s one year out of college and you’ve been out six years, your lifestyles are tremendously different. You confessing to be less experienced than her sexually may make her question whether you’re as worldly and more mature as she thought you were.
So play it cool, have sex — hopefully — and then down the road you can confess your virginity when the relationship is on more stable ground.
(One caveat, if she confesses to you that she’s a virgin it’s perfectly fine for you to then confess you’re a virgin too. In fact, I think that’s the perfect time to tell her. But I wouldn’t go first.)
“I need your advice on what to do in my predicament. I have a friend, early 30’s, married, with a one and a half year old child. My friend makes a decent living and is able to support his family and his wife doesn’t have to work. I have known my friend since childhood. We usually get together on Sunday’s to watch football and see each other a few times throughout the year. I have known my friend has had an issue with abusing prescription pills. I have seen him over the years get worse and worse. Recently we went on a two day guys trip. I picked up on my friend’s behavior and his drug habit was very noticeable. By the end of the two days, my friend started getting sick from withdrawals. When we landed, the first thing he did was call his dealer to get more pills. 
Here is my question. I think the wife knows about my friend using drugs but does not know the extent of his problem. I am worried that my friend will get even more addicted and end up overdosing or end up in jail. Do you think it is worth saying anything to the wife? Should I just keep my mouth shut.” 
I think you definitely have to talk with the wife.
His addiction is getting worse and it’s not going to end well. Like you said, either he ends up in jail, dead, or bankrupt, maybe even two of these three things.
So you need to bring in as many allies as you possibly can to try and help your friend fight this addiction. You can’t do it alone and his wife needs to know everything you know about this issue. I’d say the same thing about his parents, honestly, if he has a decent relationship with them at all. In fact, if the wife blows you off, I’d go to his parents too.
Speaking as a parent and a spouse, I’d want to know about these things if they were impacting my own family and loved ones and I suspect the vast majority of people reading this question would feel the same.
Good luck.
“My wife and daughters were devastated when Trump was elected.  Personally, I find Trump quite funny, enjoy his blunt talk, and think he raised a bunch of valid issues, but I pretend to be upset that he’s President so that my wife will continue to have sex with me.  Is this just common sense on my part, or will keeping it up for (at least) four years eventually erode my self-respect?”
I’d go with a preemptive attack and just say you are tired of talking about politics because all it does is make you angry.
Boom, that way you get out of the conversations and your wife thinks it’s because you agree with her that Donald Trump is awful.
My wife didn’t vote for Trump and neither did I — I voted for Gary Johnson — but I’m convinced we’re going to get an invite to the White House.
And I’m pretty excited about it.
I would go to the White House no matter who the president is because I think you show respect for the democratically elected president even if you didn’t vote for him yourself. Plus, what has Trump actually done that is that bad? I feel like the last person in the country that isn’t absolutely furious every waking moment of his or her life.
George W. Bush took us to war in Iraq and we spent trillions of dollars on a failed attempt to turn them into a vibrant democratic republic. That’s infinitely worse than anything Trump has done. Trump said bad things on an Access Hollywood tape a decade ago, but so far he hasn’t gotten any blow jobs from interns in the White House. (That we know of.)
So what has Trump done that’s so bad? He’s sent Tweets that upset people and sometimes been a jerk to reporters and other critics. Is that really that bad? Come on, the stock market is at an all-time high, the unemployment rate is near an all-time low, per capita income has never been higher in the country’s history, I just don’t understand why people are so angry right now.
Maybe things are going to get awful in the next three years, but if Trump can reform the tax code and make it more efficient and effective I tend to believe the economy is going to be fine. Sure, North Korea is run by a mad man, but that’s been the case for twenty years. Hopefully at some point there’s a coup in North Korea and we can eliminate the threat there.
But even if we don’t eliminate that threat, it’s not like Trump created the situation in North Korea. If anything, George W. Bush picked the wrong country on the Axis of Evil to invade. We should have taken out North Korea over a decade ago instead of Iraq.
Maybe I’m crazy, but I think things are going pretty well in the country and I expect them to keep going pretty well. But what do I know, I’m just the King Solomon of the Internet.
“Need a debate settled. I bought Packers vs. Cowboys tickets from a guy who has Cowboys season tickets.  This guy is an acquaintance in a fantasy football league. (The league has been together for 8 years and he only joined last year as 1 member dropped out and we needed a replacement). He has 4 season tickets and I bought all 4 with the intention of taking my son and 2 buddies. 
The 2 buddies were going to pay me back for the tickets.  Long story short, 2 weeks before the game the 2 buddies back out because they are pussies and their wives run their lives.  So I post 2 of the 4 tickets online for sale, and they sell.  The acquaintance that I purchased the tickets from loses his mind because I sold 2 tickets for more than what I paid him for all 4. 
I basically tell this guy to kiss my ass, I bought them from him for the exact price he asked for them (which was more than face value) and when my pussy friends backed out I sold them for enough money to cover all my expenses for the trip. Am I wrong for selling these? The FF League is split and we need your vote to settle this!”
This is a no brainer, once you bought the tickets they were yours to do with as you see fit. I’d see the other guy’s argument if he’d given them to you for free so you could take your kid and your friends and then you turned around and profited from them yourself by selling something you go for free, but he charged you over face value himself for the tickets.
So he already profited off the tickets, how can he be upset that you did as well?
Furthermore, you used half your tickets and took you and your son. And the only reason you put the other two tickets for sale was because your buddies — who were supposed to reimburse you for their two tickets — backed out and the people you expected to use them weren’t there to use them.
I don’t see how you did anything wrong here and I don’t even understand how any reasonable person could believe you did anything wrong either.
This guy sounds like an asshole and anyone supporting his side in your fantasy football league is an idiot.

“Our fantasy football league decided that the loser would have to smoke crack. Just one legitimate hit of crack cocaine (no photos and no filming of the act). Or they could add $1000 to winners pot.

Everyone seemed ok with that because it would be hilarious to watch one of our completely normal upper middle class friends smoke crack …. or make the league quite a bit more profitable for the winners

Only issue is that no one wants to procure the crack rock / crack pipe.

How difficult will this be for me to acquire and how risky is the process?”

Who the fuck smokes crack instead of ponying up an extra thousand dollars not to smoke crack?
I don’t know what it would cost me to be willing to try crack, but I’m pretty confident it would be in the millions of dollars. Do you know how many people get shitty crack and have significant health issues? Plus, would it be fun to be the only dude who smoked crack while everyone else is completely sober?
That just seems insane.
What if you got arrested trying to buy crack to fulfill a fantasy football bet? What if you got robbed and shot? Also, what are you going to do, drive to a random inner city neighborhood and ask people where to buy crack? Would you help a random white dude — I’m guessing you’re white — buy crack if he asked you for help or would you think he was a cop trying to bust you for drug dealing?
I lived in an inner city neighborhood for eight years and had no idea where to buy crack. I guess if I’d needed to buy crack I would have gone to the local liquor store and just asked people standing outside the liquor store where to buy crack, but those people don’t seem very reliable and I’m not sure they would know.
So I’m not even sure how you’d go about buying crack.
Anyway, just pay the extra $1k if you lose or come up with another fantasy football challenge that doesn’t risk death and/or jail time.
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.