Anonymous Mailbag

It’s Tuesday, time to dive into the anonymous mailbag and make your day pass faster than it otherwise would.

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

Here we go:

“Hey Clay, what do you think about men wearing women’s panties? I was doing the wife’s laundry the other day, and it got me thinking about how boring and mostly uncomfortable men’s underwear is while hers are soft, lightweight, and stretchy. An internet search on Amazon lead me to discover that apparently a bunch of dudes wear panties. At least half the reviews of this one type of women’s panties are from guys that say they are the most comfortable thing they have ever worn.

What’s your take? Is this weird, gay, crossdressing? What if the guy pooping next to you was wearing them?”

I mean, wear whatever you want, but are there really that many guys who think their underwear is uncomfortable?

I see way too many young guys wearing super tight pants that give their cock and balls the frozen Han Solo look — you know how Han looked in “Empire Strikes Back” when he got frozen, that’s what your cock and balls look like in these tight ass pants, all smashed up against the fabric in uncomfortable positions, I have no idea how your cock and balls even breathe.
There’s no way any of you can produce functional sperm if you’ve been wearing these pants for decades.
Anyway, back to you wanting to wear panties.
You mention you had this thought while you were doing your wife’s laundry. (Good for you, by the way, I don’t think I have done my wife’s laundry in 15 years of marriage). Do you think you might be attracted to her underwear — that is what she looks like in it, and sort of projecting that attraction onto yourself? I ask this because for decades I haven’t been able to walk by a Victoria’s Secret in the mall without thinking how incredible women look in their underwear.
Now, mind you, I don’t want to wear it myself, but I’m attracted to their lingerie because I’m attracted to what the women look like in their lingerie. Just seeing the lingerie, even without seeing the women in the lingerie, can make me think positive thoughts about the lingerie. It’s Pavlovian.
The same thing is true if, for instance, I come into our closet and see my wife’s underwear thrown down on the ground, I think about her in that underwear and it creates sexual thoughts. This how men are, this is how our biology works.
It’s also a big reason why Victoria’s Secret has been successful over the past several decades — because they create male desire through selling women lingerie. Women like the power that they feel when they wear this clothing because of the response it engenders in men. (But one of the ironic challenges Victoria’ Secret has right now, especially given the question you asked, is there are many competitors making underwear that feels more comfortable than the sexy underwear Victoria’s Secret sells to women (and men). It turns out the best way to compete with Victoria’s Secret isn’t by trying to sell sex to women, it’s by trying to sell comfort to them instead. Who knew that French Maid lingerie with wings on the back wasn’t comfortable to sleep in or wear outside of sexual activity? Total surprise to me.)
Now back to your question.
My first thought is what’s your wife going to say if you start wearing panties around the house? She’s the one who will see you in these panties the most. Is she cool with it? Have you discussed this with her? That’s a conversation I think you need to have. My second thought is, are you wearing it only for comfort? If so, have you tried out all types of male underwear and truly found them lacking? My third thought is, I don’t think it’s crossdressing if you are doing this entirely for comfort. I think crossdressing is about trying to become a woman, it doesn’t sound like this is necessarily your goal here. But are you being honest with yourself. Are the panties the equivalent of just the tip sex. Because if so, the next thing you know you’ll be wearing hose, heels and dresses in the privacy of your own home.
Finally, how many people actually see your underwear on a daily basis? You mention a co-worker seeing you in the bathroom, but I don’t remember the last time I saw a man’s underwear in the bathroom. I think that’s pretty unlikely. The only place I can think of where a man might see another man’s underwear is in the gym. So imagine you’re in the gym and you are getting changed to work out and you have on panties. Are you cool with everyone else knowing about your panties? Are they so noticeable as panties, by the way, that everyone would even notice them and realize that they’re made for women?
These are all questions I think you need to think about before you start wearing panties.
Ultimately my advice here is do whatever makes you happiest and most comfortable.
There’s nothing particularly “wrong” with the decision you make, but I think you need to be prepared for the reaction.
Honestly, if I started wearing panties, I’d just announce it to the world and roll with it. There’s 100% chance at our Halloween party that while I’m filling up a beer for a woman (or man) I haven’t seen in a while, I’d open up the conversation with, “So I started wearing panties last week, loving them so far.”
But be sure you tell your wife what you’re doing before she thinks you’re sleeping with another woman in the house when she sees panties that aren’t hers in the laundry.
“I’m 35 and still really close with 4-5 guys from college. One of those 5 in particular, who was my college roommate, moved away for work, got married to a girl none of us really got to know until the wedding weekend. To say they have had marriage issues would be a vast understatement.
He caught her cheating on him in March, but he didn’t want to end it so we reluctantly supported him giving it some time and hopefully some counseling. Fast forward to this past weekend. For the FIFTH time since March, he caught her lying and still communicating and seeing that guy. Along the way we have yelled at him, cried with him and everything in between to try and get him to leave her, but for whatever reason he won’t do it. We have pushed so hard at this point he is beginning to cut of us off (not call us back, ignore messages, etc). He continues to try and make it work with a woman that has betrayed the marriage over and over and push the friends that want to help away.
One of the reasons all of us have been able to stick together all these years after marriage and kids is our annual guys (fantasy draft) trip. It’s exactly the kind of trip you are thinking. Great food, too much to drink and a 35 yo hangovers to go with the fun. And now this guy is skipping it to go to a wedding of his cheating wife’s friend (that he doesn’t even know!!) instead of our trip because it “might help them.” Put aside this guy has a bit of a drinking problem and clear self-esteem issues, we now have a hard time not feeling angry at him. If you told me a year from now I wouldn’t be talking to him anymore, I wouldn’t be surprised. But I don’t want it to be that way, just not sure how to avoid it at this point.
He was my best friend and roommate in college and now we might lose him to a cheating wife and feel powerless to stop it.
Hopefully an outsiders perspective can see something I don’t.”
This is going to be difficult for you and your friends, but I’m not sure what else you can do at this point.
You’ve told him that he needs to leave her and for whatever reason he’s not willing to do that right now.
The fact that he’s shared very intimate details of his marital problems with you — this isn’t the usual she spends too much money or we don’t have enough sex level marriage complaints — suggests he values your opinion, but you’ve made your opinion clear and he isn’t listening.
There’s nothing else you can do right now.
He’s hellbent on saving a marriage that doesn’t seem worth saving to you. But to him, for whatever reason, it does seem worth saving.
The only thing you can do is tell him your opinion and be there for him when or if he ends up eventually getting divorced. You can also let him know, and this is often significant, that he can find someone better. Often if someone has self-esteem issues one reason they stay in a bad relationship is because they’ve convinced themselves they can’t actually do better.
Letting him know there are many better options out there for him is important.
Having said all of this, the part of this email about the fantasy football trip seems way less significant than the rest of your email. Your buddy is dealing with a major personal life crisis and the breaking point for you and your friends is that he’s missing the fantasy football draft because he’s attempting to put his marriage back together again? Of all the things you can be upset at him for, this one seems pretty damn minor.
(One additional caveat: you didn’t mention kids. If he’s staying with his cheating wife because they have kids and he doesn’t want to get divorced that’s a pretty significant detail too. Once kids are involved ending a marital relationship becomes a much bigger deal. Before kids are involved it isn’t anywhere near as big of a deal at all.)

“I have a new twist on fall weddings that I haven’t seen covered in the anonymous mailbag, and honestly I’m not sure what the right solution is.  Other than my time in the military, I have lived in South my entire life and as such I was raised to know that fall Saturdays were gifted to us by the Lord to watch college football. 

A few years ago I moved to Colorado for work and met a woman and we now live together.  All is good until last week.  She informed me that we have weddings to attend each of the next three Saturdays. I thought it was a joke, and laughed it off. A few days later she’s talking about what to wear at the weddings and I realized that she is serious. It turns out that she (and her entire family) didn’t realize that fall Saturday weddings are non-starters, and they all think that I’m being ridiculous for not wanting to attend. I thought a compromise would be that I can go, watch the game on a TV or my phone and leave quickly to get home, but it turns out that two of the weddings are in the mountains which I’m confident will have no wifi. 

Now I’m a Vanderbilt alum, and I know what’s coming this year, but the idea of missing games is making me sick.  What if it pull off a huge upset and I miss it? Also, what about the precedent that it is setting? What’s your thoughts on helping her understand the cultural implications for a Southerner missing Saturday football?”

Three straight fall Saturday weddings is simply unacceptable.

I mean, it just is.

Even for a Vanderbilt football fan.

Now I know I have a bit of a unique job, but my wife just left town last weekend to go a fall wedding in Idaho. The idea that I would go was just a non-starter. So she went on her own and had a good time with her family and I stayed back here, kept the kids, and watched games all weekend.

This is a larger issue i feel strongly about, but I really don’t understand the necessity of going to weddings of people you don’t know very well with your girlfriend or spouse. (Or boyfriend or husband). For instance, it doesn’t sound like you know any of these three people. Why in the world should you have to go to their weddings? I understand if it’s a close family member or something of that nature, but put it this way, if suddenly you were only able to go to half of the weddings you’ve attended in your life thus far, would the half you missed really be a very big deal at all?

Of course not.

If your girlfriend wants to go to all these weddings, more power to her, but you don’t need to be there for all of them. And certainly you don’t need to go to three straight weeks of weddings.

I’d tell her to pick the one she most wants you to attend and you go to that one, the other two she can go on her own.

Having said this, in an unbelievable Outkick coincidence, both Jason Martin, who was my producer on the radio show and who wrote for the site for years, and Lori Kelly, who was Outkick’s editor for years, are both getting married this fall.

Jason is on a Sunday here in Nashville, which actually isn’t a big deal because he picked the Sunday the Titans play on a Thursday night for his wedding.

But Lori is getting married in November in the Florida Keys.

And I’m officiating her wedding. (The only other wedding I’ve ever officiated lasted less than a year.)

So even I’m willing to break my no fall wedding rule — and go to two of them — when it comes to people that I’m very close to. Plus, let’s be honest, I’m going to do an incredible job as a wedding officiant, how could I possibly miss this?

Regardless, the clear solution here is you negotiate to limit your wedding attendance. There is absolutely no reason at all why you need to go to weddings on three straight Saturdays.

“I need your help here man. One of our good friends just recently got back together with his ex, whom he dated for a couple years on and off. It’s important to know they’re both pretty religious, except he gets way more into it when he’s with her. But anyways, she broke up with him 2 different times before because, “God was telling her to.” A load of crap if you ask me. He finally broke things off with her the last time and they have been separated for the last few years.
Fast forward to now, and the man is already looking at rings when they just started going out again 2 weeks ago! He says he wants to propose in 4-5 months. He is 23 years old and she is still 21. She’s still in college and he is working in construction, despite having his degree. Also, be aware that she tells him she’s abstinent, although we all know she had sex all the time in high school. She also lets him eat her out and eat her ass but she won’t return any favors, at all! (Not even a handjob, even though we all know those suck). 
I’m not sure if he just doesn’t care about all the bullshit she gives him and has put him through or if he’s completely oblivious to it. I don’t care if they want to be together, but how do my friends and I stop this man from proposing entirely way too soon?? Or do we let him go through with it and eventually get divorced in a few years?”
Again, there’s no good solution here.
You can try to blow up his decision making here — and I think you should — but the more aggressive you push against a relationship like this the more he may be drawn to this girl.
Which is why I think the bigger question you need to have him answer is this: why does he feel compelled to get married at such a young age? Is it just so she’ll sleep with him? That might have made sense in the 1930’s, but sex is not in short supply in this country. Is it because he’s afraid she’ll leave him again and if he proposes that way he thinks she won’t leave him again? That’s pathetic because it actually just reiterates to her what a wuss he is and how much control she has in this relationship.
In any relatively new relationship there needs to be a healthy fear that either party might leave for someone else. (I’m not saying this when the relationship has been going on for years, I’m talking about when it’s just getting started.) Otherwise you end up with fundamentally unequal relationships from the start where one party is always terrified the other might leave and so they never feel comfortable actually being themselves.

Most importantly: No guy, and I mean no guy, should be getting married at 23 years old.
Especially when a relationship has only been going on for a few weeks or months.
That’s just crazy.
And I say that as a guy who got married when he was 25.
It’s just too young for guys to get married.
So rather than attack the girl he’s marrying I’d attack the idea of marriage at this age at all. That’s probably a more productive means of attacking his decision-making than by attacking the girl he’s planning to marry, which could end up just driving them closer together.
Good luck.
“I started dating this girl who was home from college this summer.  I am 27 and sort of settled in our small town (about an hour from her university). She’s 20, a junior, and probably going to post grad somewhere in the Southeast within a couple hours of our hometown.  She’s the total package, with big dreams, but wants to settle in or near our hometown.  I want to keep seeing where this can go, but have reservations about dating a hottie in college whose going to be consistently a) in an environment that’s conducive to be unfaithful and b) juggling time management as both of our schedules are pretty full.  It’s been a fun summer with her but we are entering “this is going to be a serious commitment” territory. I want it but I have concerns. Is the risk worth the reward here?”
You guys have totally different lifestyles right now.
So if you’re going to date her you need to be honest with yourself — are you the kind of guy who can go to bed at 11 on a random Tuesday night knowing she might be out at the bar until three in the morning and you might have no idea how her night ends or what she decides to do? (Especially when you know that bar will be filled with college guys who are happy to hit on her and don’t care about her “old ass” boyfriend who lives in a different town.)
The college lifestyle is not very similar, at all, to the lifestyle you’ll be living.
As if that weren’t enough she’s got two more years in college and you’ll be approaching thirty when she graduates. As far as she and her friends are concerned you’re an old man. (Seriously, when you’re twenty someone who is close to thirty seems like a really old person. Remember, when you’re twenty you’re as close to ten years old as you are to thirty years old. That’s basic math, but when you think about it, it will blow your mind. For instance, I have my fifteen year law school reunion this fall and I just realized in the past month that at the age of 25, when I graduated law school, I was as close to ten years old as I was to forty. Forty seemed like super old at 25, now it seems like I barely blinked and fifteen years have passed. So it may seem to you like 20 and 27 are relatively close together, and they are if you were in your thirties or forties or fifties, but they aren’t very close together when you’re twenty. A couple of years seems like a lifetime when you’re her age.)
So my point here is that you guys aren’t that far apart in years, but your lifestyles are wildly divergent right now.
What’s more, you say she wants to go to grad school after she’s done with college and that’s ever farther away from where you live now. So what’s your best case scenario, to be in a long term relationship with a twenty year old until she eventually moves back to the town where you live in five years?
Is that really very realistic?
It seems pretty optimistic to me. Primarily because I think there’s a decent chance you know what you want in life, but a much smaller chance that she knows what she wants in life.
I focus less on age than I do on lifestyle when it comes to relationships.
And your lifestyles are very different right now, which create substantial obstacles for both of you in the months and years ahead.
Good luck, but I wouldn’t get too serious here if I were you. (Or her).
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.