Anonymous Mailbag

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It’s Tuesday, which means it’s time for the anonymous mailbag.
I’m heading down to Birmingham as soon as “Lock It In” is over this afternoon to play in the Regions Pro-Am as part of a group featuring John Daly, Kirby Smart, Taylor Hicks, and Widespread Panic lead singer John Bell.
Yeah, this should be fun.
As always you can send your anonymous mailbag questions to, anonymity guaranteed.
Okay, here we go:

“My best buddy and his fiancee are set to be married in July and my ex is a bridesmaid while I am the best man. I set my buddy up with his future wife at a bar back during freshman year in college and in return, his fiancee set me up with her attractive friend during my senior year.

After we started dating I fell for this girl and we got very serious with each other near graduation. She was taking on a job as an engineer (crazy good starting salary) and I was enrolled in law school at a top 20 school in the same city. Things were going great until I decided to change my mind on law school to start a company with my college roommate in the summer before 1L year. As soon as I notified my ex of this decision she dumped me shortly after. She stated that she felt I wasn’t going to be able to provide for a future family and that law school was a much safer route. Later that year, I saw on social media that she returned to her old boyfriend who was med school bound.

Flash forward to the present and my company has made me millions in my 20s, while she is still dating the dude who was supposed to go to med school (he currently is a gym teacher and never attended med school). I have remained humble about my financial success and I’m pretty sure she has no idea I’ve done well for myself. Given we will be at the same wedding, what’s my play to get some revenge? It is apparent she is a gold digger and I think anything that shows I am kicking her boyfriend’s ass will rattle her. What would you do in my position? I’m looking for some elaborate plan to just make her regret dumping me because she thought the entrepreneur route wasn’t up to her standards.”

I love everything about this story from your side, but I also can’t help but feel a bit sorry for the gym teacher boyfriend. Can you imagine the hell he must put up with from this woman over his job? If starting your own business was too much of a risk, can you imagine how much she belittles this poor bastard who is a gym teacher?

That’s assuming, of course, that she hasn’t moderated her views on what’s acceptable for her family. To be fair to her, she was young then and it’s possible she’s realized she was being a total bitch in the way she treated you. Possible, but unlikely. It’s also possible she liked the other guy more, wanted to get back with him, and used your abandoning law school as her rationale rather than just tell you the truth. Possible, but unlikely.

Plus, I always think it’s funny when women have these expectations of the men in their lives. Because it’s a pretty damn traditional way of thinking, that a man should take care of you. You said she had a job as an engineer with a kickass starting salary. Why does she need a man to make a lot of money then?

It’s not as much about him, I don’t think, as it is her. She wants her husband to reflect and expand her own magnificence. She wanted to be married to a lawyer, not a guy starting his own business that she thought might fail. She considered herself a trophy wife and wanted a trophy husband.

But if that’s your goal, why not be the badass huge earner yourself? In other words, if you’re saying your future husband needs to have a great job to support the family aren’t you essentially acknowledging that you won’t be able to do that yourself?

I never looked at the woman I was dating and expected her to provide for my future family. Because I was planning on doing that myself.

I think every individual should plan on this as well, whether you’re a guy or a girl.

As for how you should make her aware of your company’s success, you could do the usual things — show up in an insanely expensive car, give a way over the top gift to the couple getting married, buy an extraordinarily expensive watch and roll up your shirt sleeve to make sure everyone (who knows how much these watches cost) sees it. But instead of doing all that I’d just tell her directly.

Pull her aside at some point during the wedding festivities or rehearsals and say, “Hey, I know we didn’t necessarily end things the best way, but I want to thank you. You may not realize it, but you doubting whether or not (insert company name here) would work convinced me I was going to have to work twenty times as hard as I thought I was. And I did. Last year my company did (insert revenue here) and it’s now worth (insert company value here.) There’s no way that would have happened if you hadn’t broken up with me. So, seriously, thank you. I would never have worked this hard if we’d stayed together. You breaking up with me was the kick in the ass I needed.”

Is this a total dick move where you brag on yourself while pretending to give her credit for that success?


But I love this move because it flips the script on her. She dumped you because you weren’t successful enough for her, but you thanking her for your success shows you believe — even if you don’t actually believe it — that in order for you to truly succeed she had to be outside of your life.

I just love it.

I would pay to see her face during this conversation?

Just make sure no on else is around to overhear the conversation, especially the gym teacher boyfriend. I actually feel sorry for him. Because while he’s drunkenly banging her in the hotel room after the wedding, if she’s still a gold digger she’s going to be staring at the ceiling thinking, “Why did I pick the wrong guy?”

Which is your ultimate revenge.

“Proposing to my girlfriend this weekend. Any advice on what to say? I have everything planned out but what’s actually going to come out of my mouth when I’m down on one knee. Need some wisdom here.”
Keep it simple.
I’m not a big upset the conventional cliche guy when the conventional cliche works for almost everyone. It’s why even though I’m a writer I wouldn’t write my own vows at a marriage ceremony or anything like that. I just think it looks like you’re trying way too hard when you write your own vows, like coming up with your own happy birthday song lyrics to replace the ones that exist for Happy Birthday now.
Stick with what has worked for almost everyone for hundreds of years, don’t overthink this.
Drop down to one knee and tell her you’ve known this moment was going to come since — pick a moment the two of you shared that doesn’t involve sex, even if the moment you knew you were going to marry her was during sex — and tell her you’re excited to spend the rest of your life with her.
Then pull out the ring and pop the question.
(You will be astounded by how quickly this news will spread so make sure you tell your own parents, if you haven’t already, about the engagement quickly.)
“I really need an outsiders help with this one. I am a 27 year old guy. I have a best friend who has been happily married for three years. We have been friends since we could walk. Grew up together, played high school sports together, and have remained close ever since. I am single and spend a lot of time third-wheeling with friends that are married or dating. I went through a long term relationship break up about a month ago and haven’t really tried to pursue another girlfriend (outside of a single one night hook-up).

My best friend and his wife have been trying to get pregnant since they got married. They have been to multiple doctors and recently found out that he is the reason they are unable to have kids. Two days ago I went to grab a beer with him after golfing and he asked if I would help them have a baby. I ask how that would happen and he suggested I would just jack off into his wife and that would be the end of it. I told him hell no! I mean that would be super weird.
Fast forward to yesterday, he comes over to my place and says he has to find someone to help them and I am the only one he trusts. I suggested adoption and he said his wife wants a baby that is hers. I told him I would think about it. He promises no one will have to know and that I won’t have to do a thing. I really want to help them but I don’t know if this is right for me to do.”
First of all, I think you probably misunderstood him here.
I think he probably said you would have to jack off — meaning into a cup at an insemination facility — and then they’d use your sperm to inseminate his wife. Not that you’d have to jack off into his wife. (Although it’s much funnier to think about you jerking off into his wife and her having to shovel your sperm into her like a shortstop fielding ground balls.)
It’s also hysterical to think about how many times you’d have to do this. (Even funnier to think about if you ended up being incapable of having kids too and all of this was for naught. Talk about embarrassing.)
Since you clearly aren’t a reproductive technology whiz, many couples use sperm donors to have children.
Your buddy either can’t afford an anonymous donor or he’s convinced himself you’re the best option to give his wife a child since he’s great friends with you.
Personally, I think the entire thing sounds really awkward and I’d decline if I were you. Do you really want to spend the rest of your life knowing that you’re the biological father of your best friend’s son?
I don’t think so.
And I can’t really think he believes that’s a good solution either. I think he’s probably just desperate.
So I’d respectfully tell him no.
“My wife accepted a job in Charleston SC. We currently live in San Diego CA. We’ve made up our mind and we’re moving in about 2 months.
The problem we’re getting is from our parents.  Not the ‘why are you moving so far away’ problem.  It’s more of a ‘why on earth would you want to live in the southeast?’ problem.
We make very good money (around 130k/yr) and we currently live in a granny flat in a relatively bad part of town, where we can only access the property through an alley that bums regularly use as a motel/restroom.  And we can barely afford that!
We have a 15 month old boy and my wife would like another child soon.  I’ve explained that the cost of living and the quality of life is much better in South Carolina, but the only responses I get are that I’m going to a poor southern state where they eat roadkill and live in a perpetual state like the movie deliverance (not literally, but not very far off from some of the comments they’ve made).
Any advice?”
You’re in luck, when someone is this divorced from reality arguing with them is pointless. There’s nothing that you could say to convince them of how dumb they are.
As soon as your family visits Charleston and sees the quality of life you can have on $130k a year compared to what you had in San Diego they will wonder why they aren’t living there too.
So have fun and don’t worry about the criticism.
It will vanish the moment your family actually visits you.
Also, an important lesson for everyone out there, most criticism comes from people who are less successful than you are. Truly successful people don’t have time to demean the life decisions of others, they’re too busy with their own career paths to worry about denigrating others.
Think about this the next time you let someone else’s opinion of a decision you’re making make you feel bad.
And if you’re too young to realize it, the older you get, the more sense it will make.
“I’m 18 years old and nearly out of high school.
Recently, my friends and I went to a party in the town next to mine and I ran into this smoking hot girl who I knew from a summer camp. We obviously were familiar with each other, had talked before, but were never friends, or anything remotely close (she’s a year below me). Anyway, this chick has always been regarded as the hottest girl out of the group, and after working as counselors last summer, one of my closest friends was able to score with her after weeks of effort. He ended up dating her on and off for about three months until mid-fall, then got back with her on one night in January, nothing since. My friend is notorious for the way he treats girls, especially his exes. Typically, he maintains a group of about 3-4 exes who, at any moment, he’ll return to looking to hook up. Recently, he’s been pretty involved with what’s probably his closest ex. 
Getting back to me, this hot girl from the party and I started talking and had some solid chemistry. We arrived late, and she had to leave with her friends, so that was about it. Didn’t think much of it, but the next day, she hit me up and we started talking more. Pretty quickly, it escalated into her inviting me over to her house later this week to study and hang out. I accepted, and I’m pretty confident that the studying part was just an excuse to hang, and eventually do more. 
Now, I’m conflicted. I really want to get with this girl, and I’d be thrilled if it escalated into something more as we’ll both be working back at camp this summer. That said, this is one of my closest friends, and I feel obligated to tell him (I have until Friday). My fear is that he’ll do something to interfere between her and I, as he has done in the past with other (albeit less close) friends of his. What say you, King Solomon of the Internet?”
I’d stay completely quiet and say you thought you were just going to her house to study.
If something more happens, you can tell him after it happens.
Why? Because otherwise your friend will probably reach out to this girl and try to cock block you since he’s typically keeping three or four girls on a rotating cast of hook-ups. When he perceives a threat from you he may scramble to show this girl some attention and talk you down, leading to another hook up between the two of them, and cock blocking your chances.
Put simply, he doesn’t really like this girl, but he doesn’t want anyone else to have her either.
So why take that risk?
Just because he dated her first doesn’t mean he owns her.
He doesn’t date her any longer — and hasn’t for months — and you’re about to graduate from high school and head to college, meaning you may not spend much time with this guy in the years ahead. Even if he’s angry at you I don’t think he can stay angry very long and I don’t think other people will be upset with you either.
If you like this girl, may work with her this summer and end up in a potential relationship with her, why not have fun with her while you can?
To be fair, it’s possible she’s flirting with you to try and get this guy’s attention. But what do you care about that if she sleeps with you in the meantime? Just don’t go overboard with your feelings for her in the short term.
You’ll always have more sex with girls playing it cool than you will going in too hot.
Good luck.
Send your anonymous mailbag questions to, anonymity guaranteed.

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.