Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to sweep you away from work. (Ah, hell, who I am kidding. All of you bastards already took off for the 4th of July already and are probably reading this at the beach).

If you haven’t already please check out my new podcast exclusive interview series, Wins and Losses, which now has six full episodes up and ready for you to listen to. This week’s guest is Yahoo Sports national columnist Dan Wetzel. Trust me, if you’re going to be on a long drive this holiday weekend and you’re interested in sports and sports media you’ll love these podcasts.

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

Here we go:

“I want to date this girl who is still living with her ex girlfriend. (She’s bisexual). I’m waiting for her to break her lease and move out on her own. She hasn’t lived on her own in a quite awhile like 6 years. She and her ex-girlfriend have two dogs. They are going to co-parent the dogs. She doesn’t know how to budget, lives past her means, and is always spending money. Is this a deal breaker or should I just shoot my shot?”

I mean, how hot is she?

You’re a dude, nothing is a deal breaker if she’s hot enough.

I kid, I kid (kind of).

Look, we’re not talking about marriage here. We’re talking about whether you should try and hook up with a single bi-sexual chick. Given that many people exit relationships and try for the opposite of what just failed for them, you, as a heterosexual man, might be exactly what she’s looking for.

You say you’re concerned because this girl “doesn’t know how to budget, lives past her means, and is always spending money,” is that really a surprise for any person in their twenties? Are you hiring a financial adviser or trying to find someone to hook up with? The big upset here would be if she was Warren Buffett, not if she was a twentysomething who sometimes made questionable financial decisions.

As for the co-parenting of the dogs, I do acknowledge that’s a risk because it means this girl and her ex are always going to be in contact with each other, meaning there’s always the possibility they rekindle their relationship, but, again, you’re not talking about a long term relationship yet, you’re just asking whether to pursue this girl or not.

Plus, is it really that bad of a story for you to have to share at the bar if the girl you’re dating dumps you to go back to her girlfriend? That’s a story I’d want to hear, it seems like bar gold.

So what do you have to lose?

Go for it.

“I’ve been dating this girl for about two months. As an attorney, I am in a profession in which the public perception is that we make a lot of money. But since I am young and fairly new to my job I am not making a ton of money right now.

Anyway, we went to a disaster of a wedding last weekend (the groom hit on my date and tried to kiss her at the end of the night) and after some drinks, she said she wouldn’t want an engagement ring that is less than 1 carat. She also randomly asked if my boss would give her money if he liked her. And in the past, she has made passing comments that she has expensive taste.

My question is this, should I write off these comments as harmless drunk comments or does she like me because she thinks I am rich/going to be rich? And is talking about an engagement ring two months into a relationship a red flag?”

I need to hear way more about the groom trying to kiss your date the night of his wedding, honestly. That sounds like a hell of a party. (And, boy, if your groom tries to kiss another woman on the wedding night that bride is in for a rough, rough marriage).

Now let’s dive in to your question — your girl is clearly a gold digger. (Insert Kanye track here).

The more she drinks, the clearer that becomes.

I’m leery of women, especially if they are young like she is, who expect other people to take care of them and shower them with gifts. That’s really what all of her comments represent, the idea that she’s so desirable that men should just give her things based on that desirability.

This is the very definition of #hotgirlprivilege.

The question is how do you respond to it?

I’d toss off the boss question because that could be a joke with some truth in it — older men do often throw money at young, attractive women for no reason — and I don’t think it was intended to be serious. But the specific statement about needing a one carat engagement ring is a bit ominous — not just because she’s only been dating you for two months, but because of what it represents — the idea that an engagement isn’t enough, other women have to see her ring and be impressed. (The size of an engagement ring is a status symbol for (some) women. It’s a huge screaming sign that doesn’t just say, I’m engaged, it screams, “I’M ENGAGED TO A REALLY RICH MAN, BITCHES!”)

Now on to your question: is she with you because you’re a lawyer and she believes that means one day you will be financially successful? Perhaps. (She may also, wrongly, assume you make more than you do at the present moment). Now I’m not one of those guys who is opposed to women being attracted to success — success is attractive and there’s nothing wrong with a woman, or man, being attracted to success — but I am opposed to women who don’t seem to have any drive themselves and just want to be taken care of because they happen to be good looking.

So I think the question you have to ask yourself here is this: what ambition, if any, does this woman have beyond getting married to a rich guy? If her only ambition is to be your trophy wife, I suspect being with her gets old pretty fast.

How smart is she? How funny is she? What kind of partner would she likely be in raising children? I think every man should be pursuing a hot, smart, funny woman who will one day be a good mom. At least those were my objectives in finding a partner.

Your own criteria might be different, but I think you need to assess this woman in how she fits the traits and goals you find desirable.

What you have to decide is if this woman’s worth hanging around for. (Or, honestly, you might decide that she’s so hot you don’t care about anything else. But take it from an older dude, if all you like about her is the fact that she’s hot, eventually, no matter how hot she is, that wears off. Really, it does.)

Lots of people worry about trying to make sure their partner likes them, but I actually think it’s more important you make sure you like your partner.

The next time she gets drunk and brings up the full carat engagement ring, how about giving her a test, “So you’re saying if I gave you a half carat engagement ring, you’d say no?”

Listen to her response.

And then if you want to really come over the top with a devastating line, you can say, “That sucks, because I have my great-grandma’s engagement ring and it’s only a half carat. But I already know it means so much to me that I’m giving it to my future wife. Guess that won’t be you.”

You talk about a jaw dropper walk off line.

“So my 14 year old let my wife and I know tonight that he is gay. Neither one of us were shocked and really don’t give a fuck. She says she has known since he was 3, I’ve had a pretty good idea since he was 11. My wife and son’s big concern was telling his brothers and my religious parents, which I don’t think will be a big deal at all. 

My concern was entering high school, how he will be harassed by his peers.  They thought I was crazy.  My question is, do kids really care anymore? Is the scene in 21 Jump Street when the jock got made fun of for being masculine really how it is? Or should I pay a little more attention to the way he is treated at school?  Also, we have 4 sons.  So I’ve always thought the “son in law list” was not gonna happen.  Should I take it easy on any future son in law because he’s gay?”

First, on your wife and son’s concern about telling his brothers, you say you have four sons, how old are they? The younger they are the less I’d be concerned with telling them about their brother’s sexuality. That’s because it really doesn’t impact these other kids until he starts dating or brings a boy home to meet the family.

Then, clearly, you’d have to tell them, but until then young kids are fairly oblivious to sex or sexual attraction until they get closer to adolescence. Discussing an older brother’s sexuality with them just isn’t in their purview until it impacts their life.

Put it this way, would you sit down a young kid and explain that their older brother likes girls before he’s even dating any?

So I’d probably wait until your son starts dating or brings a boy home to broach the topic of your 14 year old son’s sexuality with your young kids. Now, if he’s the youngest kid, or your other kids are already teenagers I’d certainly have that conversation with them.

But most kids these days — SPOILER ALERT — think Santa Claus is real until third or fourth grade. If they still believe in Santa Claus they definitely don’t need to be worrying about who their teenage brother is chasing in high school.

As for how kids treat gay kids in high school, I honestly have no idea, but I think this is a valid concern. We didn’t have any openly gay kids at my high school and I’d guess most people around my own age had the same experience.

Some questions that I would have: are there other gay kids in the high school already, is it rural, suburban or a city school, how “safe” is the school overall when it comes to physical violence and fighting, what kind of learning environment do the principal or teachers create? All of those things matter in a big way, I think, to what kind of experience your son will have in the school when he comes out.

Essentially, I don’t think there’s any one size fits all experience here. In general, I think the better the school is — that is the higher the test scores and the lower the rates of violence — the better of an experience your son would have.

It’s also possible, by the way, that most kids in the school already believed your son was gay and so this will be met by a collective shrug of the shoulders and no one will care at all. I just don’t know.

Which is why I think it’s hard to forecast, but I think you’re correct to be concerned.

Regardless, I definitely think it’s something you should monitor at the school. And it’s probably worth you going in to the school to meet with the guidance counselor(s) to alert them about what’s going on so they keep their eyes and ears open to the treatment your son receives.

I also think you should quiz your son even more than usual about how school is going in the days, weeks and months after he comes out publicly. I know that kids often brush off their parents in situations like these, but it’s important that you stay engaged with him. Because you never know when he might feel the need to reach out to you.

Good luck.

“I’ll be getting married in a couple of weeks and somehow my fiancée and I have both made it through the gauntlet to marriage as virgins. 

As a man who has clearly done it at least a few times, what are a few things you think I should know?”

First, it’s going to be incredibly anti-climatic.

If you’ve waited this long to have sex — which you have since you both saved yourselves for marriage — when you’re done on your wedding night — which will probably happen quickly — you will likely think, “Seriously, this is what we were waiting so long for?”

Now in terms of the physical aspects at play, I hate to get graphic, but the first time she has sex with you — assuming her hymen is still intact — there will be blood and she’s probably not going to like it very much. (Nor are you).

On the other hand if there’s no blood and she rides you like a stallion, she’s probably done it before.

Either way, I wouldn’t plan for many fireworks the first night.

And, rest assured, that no matter when you start having sex together, eventually you will be like most married couples and your wife will lose interest in sleeping with you.

Congrats on the marriage!

“Had to laugh at the last couple of Anonymous Mailbags about vasectomies. I’m forever indebted to my wife’s OB. He was a crusty old straight-shooter. He’s shaped my views on vasectomies. 
We went in for the last appointment before our youngest son was born.
Him: “This is your 4th child. Although in Utah, you may want to have ten more for all I know. However, medically and biologically speaking, I wouldn’t be doing my job if I didn’t ask about some form of permanent birth control and if you’ve thought about how many children you’d like to have.”
My Wife: “This is for sure our last and (pointing at me) He will be getting a vasectomy.”
Him: “As YOUR doctor, that’s not what is best for YOU. Having children is a YOU problem. If YOU want to be done having children, then YOU need to have a tubal ligation. I bought my last car with cash that I made specifically delivering babies after the husband had a vasectomy. While you’re under anesthesia, we simply roll you in to the next room and perform the tubal ligation in about 5 minutes.”
Wife: ” Tubal Ligation it is.”
He saved me from the snip! Saw him randomly at a golf course about 5 years later and rehashed that story. We had a good laugh and I paid for his round of golf.” 

There you go, file this one away.

Ladies, if you already know you are absolutely certain you don’t want another baby, why not go ahead and knock out the possibility while you’re under anesthesia?

That way you don’t have to worry about your idiot husband screwing it all up. Or whining about having to go get a vasectomy one day in the future.

Okay, I have to run over to the Fox lot now and get ready for today’s Lock It In.

Send your anonymous mailbag questions to As always, anonymity guaranteed.

And I hope all of you guys have a great Fourth of July long weekend. (I’ll be working. Guest hosting the Dan Patrick show here in LA and doing Lock It In on both the 4th and 5th).

Once again, if you need entertainment on a long car ride or long family vacation, go listen to the new “Wins and Losses” podcasts. 

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.