Sending All Your Little Swimmers Into One Shallow Gene Pool, Waging a War Over $4, and Other Questionable AdviceS

Welcome to Thatz Not Okay, a regular column in which I school inquiring readers on what is and is not okay. Please send your questions to caity.weaver@gawker.com with the subject "Thatz Not Okay."

I see escorts when I'm not dating someone regularly. My favorite lady is a 40 something woman with whom I developed a friendship outside our professional relationship. On occasion we'd hang out, get dinner, talk about things. Her 23 year old daughter, whom I've never met, is also an escort. When Mother told me she wasn't happy about Daughter being an escort I promised I'd never see Daughter. Now, a couple of years later, Mother has cut off all contact with me. It could have been something I said but I honestly don't know what and can't find out. Personal and professional relationships are both done. Now I'm considering reneging on my promise to never see Daughter. Is that okay?

Thatz not okay.

It's a little hard to tell from your letter whether you are a person who exists or a P.O.V. writing exercise from an evening fiction class at a local liberal arts college. If you are the latter, stop reading now – I'm not here to do your homework for you!

If you are the former, why would you go out of your way to break a promise made to a person with whom you, at one time, had an apparently friendly relationship? Surely there are other prostitutes in the park; other escorts in the sea. Is this a two-ho town? Pop round to your local escorterie and see if you might like to have sex with someone outside that one very specific gene pool.

Beyond the sheer poor manners of it, what would be the purpose, exactly, of your sleeping with the daughter of your "favorite lady?" Would it be a way to get back at the mother for cutting you out of her life so suddenly? A way to approximate her presence, or maybe even work your way back into her life?

And what would you say to the daughter if you managed to track her down and convince her to sleep with you? A mid-coitus "You have sex just like your mother – classic Mom!"? A Walhberg-style "Say hi to ya mother for me" post-deed? Just a string of "your mom" jokes? Or would you wait until you'd romped for a few sessions to reveal your common acquaintance?

"Did you ever read The Tipping Point? Do you recall Gladwell's theory of 'connectors?' I know your mom because I used to have sex with her all the time." PRANKED.

When someone chooses to leave your life (they break-up with you, they stop accepting your money in exchange for sex and company, they move on to a new, cool group of friends whose parents let them wear make-up to school), part of the adjustment process entails deciding which of your promises to them you will keep, and which you'll let fall by the wayside. "I'll never do the David Bowie/Freddie Mercury Under Pressure duet with anyone but you" – that's probably okay to change your mind about. "I will not seek out you daughter for sex" is less mutable.

In any event, you concede that the mother in this scenario cut-off contact with you, possibly because of something you said ("I often fantasize about having sex with your daughter against your express wishes"). It might be time to pick a new "favorite."

My best friend had an out of town wedding, and I was in charge of finding a hotel room for our group of six friends, as I am the only one who had been to this undisclosed location. I also, refused to stay at a shitty motel, so I was to be the one to pick out a hotel. If we just stayed Saturday it would have been $275 but if we stayed both Friday and Saturday it would have been $150 each night. One of the friends and I had to go up early so we opted for two nights but decided to charge everyone the same. Every one had agreed to $50 for the hotel, so all was well.

After the wedding had ended, one of the friends brought up concern about how much the wedding was, and told me she had called to see how much Saturday night was, behind my back. After not letting me explain she decided she'd only pay me $30, after she had previously agreed to the $50. I feel like she worked the system to cheat me out of $20. (She's cheap, to say the least). I want to ask her to pay me the amount agreed to before the hotel stay. Is that okay?

Thatz okay.

But you may have to settle for slightly less.

From the wedding in an "undisclosed location" to the back door room rate negotiations, it sounds like your best friend's marriage kicked off with a ceremony clouded with deception. May the happy couple's life together always be tinged with secrets and spice. Mazel tov.

Before we get into the nitty gritty of who was right and who was wrong and who underpaid and who overpaid and who made a toast that was funny and who made a toast that was inappropriate and who was laughing because they were having fun and who was laughing because they were uncomfortable, we have to sort out this math.

Assuming your friend was given the same rates you were given when she called to verify the room prices, she should have worked out that $275 split six ways comes to about $46 per person. Her decision to only pay you $30 isn't any more fair than your decision to charge her a few extra dollars to cover your bonus night in the hotel. That sum is arbitrary. It's like ringing up $20 worth of groceries at the supermarket, handing the cashier a $5, and telling him "Keep the change, daddy-o." How did she arrive at $30? Did you incur an additional "dishonest asshole" tax?

At the very least, she should be paying you $45.83. Bring up the $15.83 discrepancy and request that she pay you that much so that she can feel satisfied knowing she paid exact correct amount and you can feel good at math for correcting her math.

Now. The issue at the center of your conflict is that one man's "cheap" is another man's "fair."

It's not clear from your summary whether everyone in the group understood that the lodging fee would be $50 regardless of whether they stayed for one night or two. Since you note your friend is "cheap, to say the least," it's quite possible she opted to stay for only one night because she believed this was a less expensive option. Did she know she could have camped out for an extra day at no additional charge? Being "cheap, to say the least" myself, I can tell you, there is nothing My People love more than a bargain, and I would have moved Heaven and Earth to squeeze in that extra day, had I been armed with such knowledge in her position.

Some people will say that, as Official Hotel Booker, it was your prerogative to split up the costs as you saw fit. It's true, that you did select the venue, check the rates, and book it. However, it's equally true that this job is not a difficult job. Click, click, boom, the job is done.

And, in your position, I must say, I would have prorated the cost. Everyone pays $46 (pocket that extra 17 cents – that plus a "thank you!" is just about what everyone owes you for handling the reservations), and the additional fee for the second night is split between the two folks staying a second night. I would have been very transparent about my math, so that no cheap person like me or your friend could blow in and accuse me of being a conjurer and a thief.

It's unfortunate for everyone involved that the squabble over the $46 versus $50 charge didn't take place in a long email chain or, better yet, over a conference call. Usually, in these circumstances, when the sum is so comically negligible, a third party will ride up on a gallant steed made of cash and huff "WHATEVER, I'M DONE WITH THIS; I'LL COVER THE EXTRA $25 MYSELF SO WE CAN DROP IT." These people are the most put-upon and beloved of any friend group.

I'm not sure how important honor is to your friend (is she a knight or a pirate or a Crip or what), but, since she agreed to pay you $50 prior to check-in , I think you're within your rights to ask for that amount. She may bargain you down to $46, and use the $4 to buy four items at a dollar store in tax-free Delaware. She may not bargain you down to $30.

You should not go to court over this.

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