Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag to help you pass your day.

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

Okay, here we go:

“My ex girlfriend  unexpectedly dropped off a bag of stuff on my front porch yesterday while I was gone… a bottle of wine I had left at her house, a Yeti tumbler I gave her (had my company logo on it), and a t-shirt….

Now… some context… she lives an hour away… and says she drove here because she couldn’t stand to look at the stuff any longer.. also… our breakup wasn’t amicable… long relationship, talk of marriage, our kids all love each other, etc… it’s been hard…

So she leaves this stuff… but I have never seen this t shirt in my life.  I ask her about it and she says that it’s mine and that she wore it home from my house.  Umm… no.  AND IT IS NOT MY SIZE!!.  I had been wondering if she was cheating on me before we broke up… she claims no.  Why would she do this?”

One of two things is at play here. Either it’s just an old tshirt and she really thinks it is yours, but it’s actually from an older ex-boyfriend, in which case this is just an innocent mistake OR it’s from another guy and she wants you to be jealous. (It’s possible this is potentially from a guy she was cheating on you with, but it could also be a new guy she’s already sleeping with. Either way the goal here is to make you jealous.)

My bet is on the second option.

Because do you really need the other two things she returned — a bottle of wine and a Yeti mug? That’s worth what, $50 tops?

There’s no way that’s worth an hour’s drive to your ex-boyfriend’s house.

I think she intentionally made the trip with the t shirt and put the Yeti and the wine there to make it look less obvious she was attempting to anger you by letting you see the t shirt.

Rather than let her upset you, I’d just let it go.

If she was cheating on you, so what? You’re already broken up and this is just further evidence you made the right decision to break up with her.

If she was doing this to try and make you jealous, so what as well?

I’d just move on.

“I had a friend of mine recently tell me about a job transition. At the end of the conversation they said “keep this between us for a few days.” 
Now, for something as simple as a job transition, I would feel very comfortable telling my spouse about that. It is nothing too serious, life threatening, or life changing and who is she gonna tell anyway? But it got me wondering, at what level of information where if a friend says “keep this between us” do you really have refrain from even telling your spouse?”
First, when someone says you can’t share what he or she is about to tell you with anyone else, in general I think they understand that you are probably going to tell your spouse about it. (And if they don’t understand that they need to specifically say, “And this includes your wife too.”)
There are certain exceptions that would apply here when it comes to sharing information, of course. For instance, you can’t tell your husband or wife about privileged communications if you’re a lawyer, doctor, preacher, or therapist, but those are relatively rare jobs. You also couldn’t tell your spouse about FBI, NSA, or CIA privileged materials or work-related knowledge.
But the general rule, I think, is if you tell someone not to tell anyone that a person is probably going to tell his or her spouse. Especially if it’s really interesting information. (If you know your spouse is in inveterate gossip, by the way, you should refrain from telling them more often than not, however, because you don’t want to betray a friend’s confidence.)
The only time when you 100% can’t tell your spouse, in my opinion, is if it involves a friend of yours and your wife is also friends with his wife and it’s something that she can’t know. (The theory holds true if the spouses are reversed as well.)
Let me give you a wild example here. What if your buddy came to you and said he’d gotten his mistress pregnant and needed your advice on what to do, but he swore you to secrecy in the meantime? You couldn’t tell your wife about it if she’s friends with his wife because she’d clearly have to tell his wife if she had this information. So you’d 100% have to keep that information private and not share it with anyone else, including your wife.
So I think you draw the line on keeping something 100% confidential when you know there’d be an obligation on behalf of your wife to share the information with her friends. (And if you have trouble thinking about this, put it this way, what if your wife confessed to you that her best friend had told her she thought a baby she was having with her husband wasn’t really his, but instead was the man she was having an affair with? Wouldn’t you feel like you needed to tell him?)
“A little over a year ago a new girl started at my work. We work in a small office and are both in our mid-20’s among a lot of older people, so we instantly became friends. 
At the time I had a girlfriend and she was dating someone else. I enjoyed having a platonic female friend, she gave me a great female insight, fashion advice, etc. We were both honest with each other about our dating/hook-up life and nothing was out of bounds for discussion.  It was nice to have a friend at work, and we began talking morning, noon, and night.  I have always thought she was cute but never saw myself in a relationship with her. 
We started spending time outside of work and it began to reach the point where friends and family were constantly questioning if we were together and she would receive the same questioning. My boss realizes we are close and has even said to me that he does not want two employees dating. 
Fast forward to today and we are both single. A couple weeks ago it hit me like a ton of bricks that I am seriously into her. I don’t know when it happened but now I realize I no longer want to be just friends. We have never hooked up or done anything besides flirting. 
I want to put myself out there and go for it but it’s very tricky. I love my job and am not going anywhere.  I am not afraid of rejection but I am 100% afraid of being rejected and having to see her at work every single day. 
I am at a loss of what to do. If we didn’t work together I’d go for it, but I have a great job and would hate to ruin anything career-wise.”
So you’re basically Jim and she’s basically Pam, gotcha.
It’s “The Office,” in real life.
Just like Jim did, I think you have to go for it here.
But I might be inclined to tip toe up to this relationship instead of pulling your co-worker aside and confessing your feelings for her.
Because that can be a big jump.
I get that you already know each other very well, but that would just mean if you actually did start a relationship together you’d move faster than most couples who were otherwise strangers.
The big deal is still the start of the relationship.
So why not go out for dinner and drinks with her and make a move there outside of the office. I’d make this a relatively non-sexual move — I’m a big proponent of the attempt to hold her hand move as you walk her to the car.
I think the hand hold move is the most underrated move in all of male/female relationships.
If a girl will hold your hand, she’ll kiss you, but it’s not as embarrassing to get rejected on the hand hold as it is to get rejected on the kiss.
Seriously, if you’re a young guy reading this right now, take this advice to heart.
Never, ever attempt a kiss without attempting a hand hold first.
If she shoots down your hand hold attempt, it’s nowhere near as embarrassing as if you pour your heart out to her and she shoots you down that way and then you still have to see her at work every day.
At least this way you can claim your interest wasn’t that serious. (As you cry yourself to sleep every night).
As for the work prohibition, if you really like the girl it’s a lot easier to find a new job than it is to find a girl that you really like.
Plus, if you both do your jobs really well it’s kind of exciting to have a secret workplace relationship and any boss that would fire two strong and productive employees — especially in this economy — isn’t worth working for anyway.
Good luck.
“Last Christmas my cousin gave me a DBAP shirt- I got him one as well, so you’re welcome for the beach house.

Anyway, my wife absolutely refuses to let me wear that shirt out in public, especially if I’m with our kids (2,4). So my question to you, o great wise, gay, Christian, Muslim is what do I do when two of life’s principles – DBAP and is my wife more likely to sleep with me – are in conflict with each other?

I mean I like the shirt, but sex is cool too…”

If you’re a married guy and you have to choose between sex and clothing, pick sex every time. (Thanks for the beach house).
“At what point should one stop playing the penis game? I was at a bachelor party and we were playing it. All in our early 30s.”
(If you’re not familiar with the penis game, it’s a competition where one guy says penis, initially very softly and each additional person playing the game has to keep saying penis a bit louder until someone is screaming penis at the top of their lungs.)
In your present example you’re too old to play the penis game unless you’re in a place where the penis game is relatively low on the immorality scale compared to other things you’re doing.
For instance, if you’re in a strip club the penis game is no big deal no matter what age you are.
Or if, perchance, you work for a Mexican cartel and are sawing up the bodies of people you just killed. Then playing the penis game wouldn’t be that big of a deal either.
In addition to the relative morality standards at play, this is also important: the level of drunkenness of you and, significantly the other people around you also factors in here.
You can’t be the drunk dads at Chuck E. Cheese at two in the afternoon on a Wednesday playing the penis game in front of little kids and their moms, but the drunker the group surrounding you is the easier this game is to justify.
Location, however, still matters in a big way.
I felt like such a narc recently because there were a bunch of 14 or 15 year old boys playing the penis game at an amusement park cafeteria. I was there with my three boys and these kids are screaming penis as loud as they can and I’m trying to get my four year old to eat his pizza and, of course, my boys are loving the fact that some older kids are screaming out the word penis because they are little kids already fascinated by the fact that they have penisses.
But I’m sitting there thinking to myself. “Were these kids raised by wolves? How do they not know that playing the penis game next to little kids at an amusement park is totally inappropriate. Do it on the big rollercoasters while they go down hills like everyone else. What a bunch of amateurs.”
Okay, kids, keep the questions coming to
The mailbag is only as good as the anonymous questions we get.
And if I’ve already solved every question in America, I may have to retire the anonymous mailbag one day. So you better keep the questions coming.

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.