Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always you can email me at any point with your questions, anonymity guaranteed. I’m at You can also search past mailbags by clicking on this link — anonymous mailbag. 

Here we go. 

Hey Clay,

First of all I absolutely love everything you write and talk about, keep it up.

To set the background for this story, I’m a 20 year old guy in his 3rd year of college at (edited). So I recently got a pretty interesting request via Tinder. A 19 year old girl reached out to me to have casual sex with her for the sole purpose of her getting pregnant so she and her female partner (she’s bisexual) could have a child without going through all of the legal paperwork and cost of receiving a donation from a sperm bank. Now, I know this sounds odd and unlikely, but I did lots of background research and I can confirm she does have a girlfriend and at least exists and hasn’t lied about anything. Now this girl is above average when it comes to looks, and at first glance it seems harmless. She would drive up a few hours and get a hotel for a night and we would have a night of fun with no protection. I’ve already made sure we are on the same page that I would not be contacted by her after this for any reason and I don’t even want to know if she ends up getting pregnant or not. She’s also agreed to sign something that I am to have no financial responsibility should she really get pregnant. So overall, she gets free sperm with no paperwork or hassle, and I get a night of casual sex with no requirements afterwards. At first I thought it sounded great but I’m having second thoughts… Even though I won’t know if she ends up getting pregnant or not, I don’t know if I like the idea of having a child out there that I know nothing about and that knows nothing about me. It just feels wrong for some reason. What’s your opinion? Do I go through with this or not?

The sooner I get a reply to this, the better.”

So you’re in college and you’re contemplating having sex with a 19 year old who wants to get pregnant so this girl and her girlfriend can have a child without paying for a sperm bank. And you met this girl on Tinder? I feel like we need an intervention for this girl. No 19 year old should ever get intentionally pregnant. I mean ever.

Several additional thoughts: 

First, the odds of getting pregnant from one time of sex are really low. So is she traveling throughout the Tinder universe having unprotected sex with all sorts of guys in order to get pregnant? Who is paying for her travel? Isn’t that more expensive than a sperm bank?

Second, are you, a college kid, drafting paperwork that disavows your parental responsibilities should she get pregnant? I’ve never drafted anything like this, but I’d be nervous about how well it would hold up in court. Also, if you have to draft paperwork disavowing your parental responsibilities before you have sex, this is way too much effort to have sex for a college kid. 

Third, how much does sperm at a sperm bank cost? It’s not that expensive, right? This entire story sounds like a sham that ends with you showing up at a hotel room, getting drugged, and waking up in a bathtub full of ice without a kidney. 

Fourth, say she does get pregnant — a kid in exchange for one night of sex? Trust me, this is a bad trade. 

Fifth, this girl’s decision making is too crazy for you to be willing to have unprotected sex with her.

My advice, stay away. 

“Is it weird that I don’t masturbate in my bedroom because I feel like it insults my marriage?”


“My two friends have this girl over and she’s a solid 8. Honestly, the girl is just a friend to them because her personality makes her pretty much undateable. However, she has hot friends and she’s usually cool to just hangout with in doses.

So she comes over and all three of them just get drunk, especially the girl. After about 3 or 4 hours they’re all shitfaced. Long story short, one conversation led to another and she asks them if they wanted to have sex. Of course they both say yes – she’s hot – but her one condition is it has to be a threesome….

One of my friend doesn’t care (just no eye contact) but for the other it’s a deal breaker. So they both argue over whether they should do it or not for like an hour but eventually the alcohol wears off, the girl gets tired, and then nothing happens for either one.

I’m on the side of my friend that was down for it. That’s a maybe once or twice in a lifetime opportunity. The other guy just didn’t want to be “gay.”

Who are you siding with?”

The guy who would have had the threesome and not made eye contact with this friend. 

In that situation — which I’ve never been in, all of my threesomes were with two other dudes — you both make an agreement that one goes up top and the other goes down low and you never find yourself on the same side of her body.  

I just don’t get the gay thing that the other guy is worried about, it’s not like you slip and accidentally end up with a dick in your ass. (I’m talking about the two guys here. Unfortunately for women this actually happens to you all the time). Life advice: If you ever find yourself thinking, “I don’t know, I’d hook up with this hot girl, but I’m worried that I might end up touching my buddy’s dick,” it probably means that you want to touch your buddy’s dick. There’s nothing wrong with that, but it has been my experience that the more homophobic you are the more likely it is that you might be gay.

Put simply: If the girl is hot enough, I think everyone has to be willing to make this decision. I mean, are you really telling me that if Charlotte McKinney said she’d hook up with you tonight, but the only condition was your friend had to hook up with her too that you guys would pass on it?

Come on.  

“I am 24rys old, and I think I have a Sugar Daddy.

I’ve been steadily banging this dude for the better part of 2yrs, maybe like 3yrs at this point. Perfect setup: He’s about 10yrs older than me, the CEO of a VERY successful company, loaded with money, takes me out to dinner/bar, I get sporting events tickets, hotel rooms if I want them, very easy on the eyes, easy to talk to, a blast to be around, a great person to bounce ideas off of… there’s just one tiny little catch: He’s married with a young daughter. Now. We talked about this before I willfully consented to this ‘agreement’.. his marriage is a sham. He can’t leave her or divorce her, he would lose his whole fortune and the credibility he has gained by building this company from the ground up would be lost, not to mention whatever would happen to the company itself. There was no prenup. He’s one of my former bosses, so if by chance people do see us out together we smoothly make it work (although we both make every effort to NOT get caught publically) and after 2yrs we have the game on lock. He always says there is “chemistry” between us, and there is no doubt that’s true. But my question to you is this: How wrong is what I am doing, I mean it has taken a serious toll on my conscience here, and how much longer should I keep this up? At this point all the cards are in my deck, but after 2yrs and a lot of fun and a ton of stories I can NEVER tell my Grandchildren… how much of a good thing is too much of a good thing? I am thinking I need to call this quits.”

First, you need to acknowledge that he’s not leaving his wife for you. Then you have to make the decision, is this relationship worth it to me? You’re 24 years old. There are a ton of normal — i.e. not rich or married — single guys you could be dating or hooking up with instead of this guy. Are you hanging out with them too and just keeping this guy on the side or are you committed to your married sugar daddy relationship and not seeing anyone else? If you’re stalling the rest of your life to wait for him, that’s bad for you. 

Basically, leaving aside the morality of your situation, what’s your end game here? The relationship has to end at some point, right? So when does that happen? It’s probably your call. If the relationship is truly taking a serious toll on your conscience then I’d think you already have your answer — it’s time to walk. 

“Dear gayest Muslim, lion loving, Gawker reader

Last Wednesday, I went to the taping of the Comedy Central show @Midnight, and pissed my pants. Not from laughter, but intentionally. It was 98 degrees in LA that day and I had 100oz of liquid prior to the show because of the heat. I even pissed 4 times before the show but it wasn’t enough. I’ve never been to late night show taping before and I didn’t know they lock you in your seat for 2 and half hours and you cant move. 30 minutes in, my body was being pushed to its physical limit. With no other options, I had no choice but to go right in my pants. Some piss dripped on the floor and onto my shoes. I sat through the whole show in soggy pants and still had to pee badly after because I only cracked the valve a little. Hopefully the guy next to me didn’t notice. What other situation in life is there where you absolutely cannot pee no matter what? Being an NFL Redzone channel anchor? Anything else? Apparently, Aubrey Plaza was erotically humping the podium but I wouldn’t know because I didn’t watch the show.”

There is no situation where a man should ever voluntarily piss himself. 


That’s because men can pretty much pee anywhere at any time. Ease of peeing is one of the primary values of being a man. I’ve admittedly created a poor example for my own boys because my four and seven year olds will pee anywhere. Especially my four year old. He prefers peeing outside to peeing inside. Who doesn’t?! The other day we were walking home from the pool and my four year old just drops his swimsuit and he’s ready to pee right there on the sidewalk. We’ve been on playgrounds and one of my kids just walks behind a bush and starts peeing right there.  

Anyway, if I had to pee that badly, I would have left the show. You can’t intentionally piss yourself. 

“I’ve been dating the same girl for about 2.5 years now. I already have the ring picked out and paid for and I know she’ll say yes anytime I ask, but there’s one last hurdle I still have to clear; her father.

I know it’s antiquated and to some degree, somewhat demeaning, to ask a girl’s father for “permission” to marry his daughter, but in my mind it’s more of a sign of respect. I don’t actually believe we need his “blessing” to move forward with our future together, but I think asking would just be the right thing to do.

So the problem isn’t the relationship, we get along great, there’s nothing I dislike about him nor do I think he holds any more animosity towards me than any father would have for a boy screwing his daughter. The hang up is that her family lives in another state, far away. So I only see her parents a couple times a year when they come to visit her.

So my question: how should I go about this? Is it socially acceptable to make a phone call? Should I wait to do it in person for an arbitrary visit that could be months away? And even then, I’m not really sure what one even says in either scenario?

As a married gay muslim, I’d like your perspective on this.”

You definitely should ask the father for his permission. (Although this is clearly just a formality, has anyone ever heard of a father saying no and the guy accepting it? This would be the biggest pansy move of all time). 

Given your situation — the geographic distance and infrequency of visits — asking via a phone call is fine. But if you see your future fiancee’s father on a regular basis or he lives relatively close to you, you should do it in person. Making a phone call to a guy who lives a half hour from you is a huge wuss move.   

Good luck. 

The anonymous mailbag runs every Tuesday on Outkick. You can email your anonymous mailbag questions to

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.