Anonymous Mailbag

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Of course, my sister (who is 24 and a successful, working professional) proceeds to black out at my wedding, and hook up with one of my groomsmen at the hotel bar after the wedding while I was with my new wife in our hotel suite. They have met before, but neither has expressed any romantic interest in the other (at least to me) prior to that night.

Not only did they hook up, but my sister chose by far the wildest of my friends to hook up with. I have seen this guy do strange drugs, bang hookers, and have to get STD tests as a result of his escapades on multiple occasions. Taking things a step further, he told our friends on my bachelor party that he has hooked up with multiple men over the past few months because he was “bored.” Obviously, this is fine from a friend perspective, because I don’t care what he does in his private life and enjoy spending time with him, but it’s hardly the guy I want dating my sister.

Fast forward six weeks later, and the two are now dating long distance (she is in the northeast and he lives in the same city as me in the south), having planned multiple trips to see each other. They waited nearly a month after the wedding to tell me, fearing my reaction, but told many of my friends beforehand, swearing them to secrecy. All of my friends have since said they would have told me earlier (which I take with a grain of salt), but wanted it to come from the people involved.

Since I found out, I told my friend that I no longer felt that we could be close because I know too much about him, and it disgusts and bothers me to think he’s dating my sister. I also told my sister that I do not approve of this choice and feel it will drive a wedge between us if they continue to date. However, this has largely made things worse as I get constant texts from my mother that while she doesn’t approve of the relationship either, my sister can date who she wants, and she doesn’t like seeing her family divided like this.

So I turn to you, the King Solomon of the Internet, to help me navigate these muddy waters. What do I do here?”

I mean, I kind of feel like this is on you. If this guy is so detestable of a human being, why is he your groomsman? If he was doing drugs and banging hookers it’s pretty unlikely you were at Sunday School while this was going on. Plus, it’s not like you just invited him to the wedding, you essentially announced him as one of your best friends to the world when you allowed him to be a groomsman in the wedding AND you did this despite the fact that you knew the groomsmen and the bridesmaids, three of whom would be your sisters!, would be hanging out an inordinate amount of time at your wedding.

You also did this despite the fact that you know it’s a cliche for groomsmen and bridesmaids to hook up. Furthermore, you know your friends. How many guys, no matter how good of friends they are, refuse to hook up with a guy’s hot sister when they are drunk at the hotel bar after a wedding? A small percentage, I’d bet. And certainly that small percentage isn’t going to made up of your drug-using, hooker banging buddy.

Having said all of this, I certainly understand there are lots of guys, maybe even most of them, who wouldn’t want their best friends from college to date their sisters. That’s simply because you know too much of their history. I think the STD tests and sex with hookers is probably off the table as reasons to disqualify him from dating your sister — after all, people evolve and change after college and if every guy who ever got an STD test in college or banged a hooker was ineligible to ever get married, a huge percentage of men would be off the table completely.

But, and I think is key, HE’S HOOKING UP WITH MEN BECAUSE HE WAS BORED!

I’ve been bored before, do you know how many guys I hooked up with to cure that boredom?

ZERO!

Assuming this is something other than a joke — he could have totally been joking about this and you might have heard it from an idiot who took it seriously — I think every woman on the planet would want to know if the guy she was dating had any history at all of sleeping with men. (In an older anonymous mailbag I said that every woman secretly fears two things: 1. her boyfriend or husband is going to kill her and 2. her boyfriend or husband is gay.)

If your friend is hooking up with guys, he’s probably gay. At an absolute minimum, he’s bisexual.

That’s 100% information your sister should have.

Hell, it’s 100% information I think you’d be obligated to share with any female friend in the same situation.

I don’t think her opinion will change based on your friend’s past sexual history — although you should encourage her to ask him to get tested one last time for STDs especially if he’s been sleeping with men — in fact, your fraternity brother’s past sexual history might even be a turn on to her because many women like the challenge of turning a bad boy into a husband, but lots of women would consider the hooking up with dude detail to be a deal breaker.

So I think your sister deserves to know that at a minimum.

As for how to handle your mom, I’d just agree with her not to get involved in the relationship. And as tempting as it might be to share this information with your mom, you certainly can’t. First, what if your buddy has truly changed and ends up being a great husband one day for your sister? Then your mom’s opinion of him would be forever polluted by things in his past she didn’t need to know. Second, your sister might stay with this guy longer because of family disapproval — frequently family disapproval backfires and makes the bond stronger — especially if it’s from your mom.

I think you tell your sister about the hooking up with guys thing and then say that’s the final word you’ll have about their relationship.

Just tell your sister, “I know you can do better,” and give her that look your parents gave you when they said they weren’t mad, they were just disappointed.

Then leave it at that.

Good luck.

“I maintained the cash and record keeping of the NCAA Tourney office pool. Half the players were friends of coworkers, people I don’t know. Turns out 4 people didn’t pay after repeated email reminders. I split the pot per the payout structure, less the uncollected funds. 

The rule on NCAA Tourney bracket payments should be simple — if your money isn’t in by tip off of the first game on Thursday then you’re excluded from the contest.

Boom, that’s easy to understand and it makes perfect sense.

Now you can make limited exceptions for people you actually know if you know they’re good for it. For instance, let’s say you’re buddies with a guy and know you can just get his entry fee the next time you see him out at the bar, then you could allow his bracket challenge to remain entered in the contest.

But as a general rule, I think you enforce the payment by tip time rule.

Because here’s the deal, I think some people try to get a free ride and wait to pay only after they know their bracket is doing well.

You can’t allow that.

As for your particular situation here — you did everything you could to collect and these four people just refused to pay.

As such, you have no obligation to pay their entry fees yourself and then give the money to winners.

At least in this situation, he is a pussy and your morals are fine.

“I have nice comfortable job right now with a salary in the low six figures. We also live in the same city as my wife’s parents who help us with our 3 kids. 

I have a job offer in another state where we wouldn’t know anyone. But it would immediately increase my salary by 50% and most likely by 100% in the first three years. It would certainly be a job with much more responsibility than I have now. 

My wife is not excited about this opportunity for a variety of reasons: move away from family, more pressure in job, etc. Tell me Solomon of the Internet, what’s the right call here?”

Doubling your salary in three years is a big deal, but you have to factor in the cost of living where you’re moving to as well and you also have to factor in that you’re expecting that doubling to occur, it might not happen through no fault of your own.

Assuming the cost of living is similar — and if it’s not, you really need to factor this in — let’s say you’re making $150k now — it’s been my experience that people who say they are making the low six figures are never making $400k, it’s usually just a little bit more than five figures — and you’re correct and you could be making $300k in three years.

But in the meantime your salary would increase to $225k.

That’s a pretty substantial difference in income assuming, again, cost of living is similar in your new location.

But, and this is key, in the short term how much will your life change over going from making $150k to $225k? I know, I know, everyone out there thinks that if they made 50% more at their job that their life would be completely different, but the truth is that’s probably not going to be the case. If you don’t believe me — and many of you reading this right now probably don’t — studies have shown that your happiness doesn’t change that much with salary increases once you reach around $75k a year in income. People consistently overvalue how much more money will change their lives. Yes, it does make things better when you go from not being able to afford rent, food, and good schooling for your children, but it doesn’t increase at the level you anticipate it would.

Here, you’re making $150k in your current job in your current city. That means you probably have a fairly decent quality of life already. (Although, to be fair, making $150k with a stay at home wife and three young kids isn’t an insanely luxurious life, especially if you live in a decent-sized American city. Again, some of you are rolling your eyes, but that money can disappear in a hurry with a family of five.)

That’s why I think quality of life comes into play here more than the financial side of the equation.

Your wife appears to be placing a large value on having her parents nearby to help. But what is the value of their help? If you move to a new city let’s say you have to spend $25k a year to get the same kind of help from someone else. (That seems like a reasonable estimate). Boom, there goes a third of your salary increase in one fell swoop.

Then, as you’ve already stated, everything in life is not a purely financial decision. Your wife doesn’t want to move and leave her parents. So you need to have a conversation with her about this. What would need to change in order for her to want to move? Clearly there’s some amount of money that would make it worthwhile. So what’s her pricetag?

Not to go all Million Dollar Man on you, but everyone has a price.

For instance, if you paid me enough I’d move my family anywhere in the world where their safety wasn’t insanely in danger. So I wouldn’t move my family overseas to Iran or Iraq no matter how much you paid me, but I’d move to London, Saudi Arabia, and Australia for the right price. There’s probably nowhere in America I’d refuse to move my family for $15 million a year guaranteed. But some places would cost less. That is, I’d agree to move to Miami for less than I’d agree to move to North Dakota for.)

So what would it take for your wife to be willing to move? If doubling your salary in three years isn’t the answer, what is? You need to know this because if there’s one family rule that I think is always true it’s this — if momma ain’t happy ain’t nobody happy.

I’m not saying don’t take this job, but I think you need to work this out with your wife.

I also think you should take a trip to the city in question and see where you might live and what houses would cost in the areas where you might want to live.

Good luck making your decision.

I mean, the answer has to be 100%, right?

I can’t imagine winning the green jacket and not involving it in sex play some way, some how. It’s the same thing with the Stanley Cup, I think everyone who has ever won the Stanley Cup has had sex with the Stanley Cup in the bed with them. (Or at least in the bedroom.)

I do think, however, that it’s more common for the woman to be wearing the green jacket than the man.

I think the woman comes out in only the green jacket because I think that’s way hotter to both members of the couple than Phil Mickelson’s fat ass hammering away wearing only a green jacket. (Does any woman reading this right now find the idea of Phil Mickelson banging you in a green Masters jacket to be super hot? If so, do you want to be my second wife when my current wife eventually leaves me?)

By the way, I just looked it up on PornHub — where “Game of Bones” has been trending all week — and there isn’t a single PornHub video with a girl in a Masters green jacket. I think that would do well every year at Masters week since every other holiday is always trending on PornHub.

By the way, you’re definitely going to hell if it’s Easter week and your horny ass is looking for naughty Easter bunnies on PornHub.

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