Is working as an escort very risky?

[+ Vegas_Millennial]

1 hour ago, KensingtonHomo said:

LOL - the amount of projection you're capable of is wild. 

And, no, we're not going to debate the use of the English language because you're not equipped for the task. 

 

[d.anders]

1 hour ago, mike carey said:

I think both @Jamie21 and I knew exactly what the other was saying.

How utterly charming.

Why does this place often feel like high school?

[+ Jamie21]

3 hours ago, mike carey said:

I think both @Jamie21 and I knew exactly what the other was saying.

Telepathic 

[+ Jamie21]

2 hours ago, d.anders said:

How utterly charming.

Why does this place often feel like high school?

We’ll be in even more trouble, possibly put in detention, if we continue this debate which has strayed well off the topic of ‘why is working as an escort risky’! 

[Wings246]

On 8/19/2025 at 11:06 AM, d.anders said:

Why does this place often feel like high school?

I don't think it's just this place.  It's everywhere.  High school never ends, remember?

Back to the main topic: please forgive my ignorance, but what are the official definitions of work and reportable income (per the US government and IRS, for example)?  If someone "innocently" claims that the monetary exchanges are "gifts" from one individual to another, will that constitute a legal mandate for the amounts to be filed on a tax return?  If the transactions are all conducted via cash (with no evidence or paper trail), how can anyone prove that it is work (assuming no sting operations are involved)?  Is it stupid and dangerous to not report the earnings on a tax return if you don't care about Social Security benefits?  Again, I can be very dumb and naive to not see the potential risks associated with this alternative/arbitrary definition of work and what some may regard as tax evasion.

Edited Wednesday at 07:48 PM by Wings246

[+ Vegas_Millennial]

6 hours ago, Wings246 said:

I don't think it's just this place.  It's everywhere.  High school never ends, remember?

Back to the main topic: please forgive my ignorance, but what are the official definitions of work and reportable income (per the US government and IRS, for example)?  If someone "innocently" claims that the monetary exchanges are "gifts" from one individual to another, will that constitute a legal mandate for the amounts to be filed on a tax return?  If the transactions are all conducted via cash (with no evidence or paper trail), how can anyone prove that it is work (assuming no sting operations are involved)?  Is it stupid and dangerous to not report the earnings on a tax return if you don't care about Social Security benefits?  Again, I can be very dumb and naive to not see the potential risks associated with this alternative/arbitrary definition of work and what some may regard as tax evasion.

Great question.  There are a few existing threads about it, the most recent one is here: 

The best answer: Declare all or most of your income, even by cash and even for tips.  If not, you'll run into problems eventually trying to prove income to secure housing, loans, and even your social security benefits.  You'll eventually do something stupid and raise a red flag to cause an audit and then you'll really be in trouble. 

Use the tax breaks available to you and take advantage of reporting income and then funneling it into investments Roth Accounts to avoid paying capital gains taxes in the future, when you've stopped escorting and need to live of the income from your investments.

 

Edited Thursday at 02:47 AM by Vegas_Millennial

[chitownguy]

17 hours ago, Wings246 said:

I don't think it's just this place.  It's everywhere.  High school never ends, remember?

Back to the main topic: please forgive my ignorance, but what are the official definitions of work and reportable income (per the US government and IRS, for example)?  If someone "innocently" claims that the monetary exchanges are "gifts" from one individual to another, will that constitute a legal mandate for the amounts to be filed on a tax return?  If the transactions are all conducted via cash (with no evidence or paper trail), how can anyone prove that it is work (assuming no sting operations are involved)?  Is it stupid and dangerous to not report the earnings on a tax return if you don't care about Social Security benefits?  Again, I can be very dumb and naive to not see the potential risks associated with this alternative/arbitrary definition of work and what some may regard as tax evasion.

Per the IRS the definition of a gift - "the transfer of property (including money or the use/income from property) to another person without receiving something of at least equal value in return".  If the exchange of money doesn't meet this standard then it is taxable income to the recipient.   Gifts over certain dollar amounts can also be taxable to the person who gives it to you.

[d.anders]

On 8/20/2025 at 3:47 PM, Wings246 said:

High school never ends, remember?

The British humor.

[+ DrownedBoy]

On 8/19/2025 at 12:50 AM, Jamie21 said:

I’m British, being rude is an art form. You probably wouldn’t recognise it unless you’ve been immersed in the culture. We can be rude with the slightest gesture, an intonation or just one apparently innocuous word. It’s even better when the recipient of said rudeness is oblivious to it because it means we’ve been so deliciously subtle that only a fellow Brit (or someone who has lived here and learned the culture) would notice it. We can then all have a laugh at the poor chap’s ignorance without obviously causing offence. 

The Japanese have you guys beat. They know how to weaponize politeness.

[+ Jamie21]

3 hours ago, DrownedBoy said:

The Japanese have you guys beat. They know how to weaponize politeness.

There’s a lot of similarities between the Japanese and British. Both islanders, both monarchies, both ritualise tea drinking, both have strong etiquette codes, both don’t say what they mean. Very similar. 

[mike carey]

15 minutes ago, Jamie21 said:

There’s a lot of similarities between the Japanese and British. Both islanders, both monarchies, both ritualise tea drinking, both have strong etiquette codes, both don’t say what they mean. Very similar. 

And at the start of last century you were allies, but it seems there were some disagreements after that. The world appears to have righted itself now. But neither that nor inscrutable humour and manners is the topic of this thread, so we move on.

[pubic_assistance]

2 hours ago, Jamie21 said:

There’s a lot of similarities between the Japanese and British. Both islanders, both monarchies, both ritualise tea drinking, both have strong etiquette codes, both don’t say what they mean. Very similar. 

That's actually very insightful, @Jamie21. Very clever analysis.

[Wings246]

On 8/20/2025 at 7:43 PM, Vegas_Millennial said:

The best answer: Declare all or most of your income, even by cash and even for tips.  If not, you'll run into problems eventually trying to prove income to secure housing, loans, and even your social security benefits.  You'll eventually do something stupid and raise a red flag to cause an audit and then you'll really be in trouble.

I absolutely agree there are inherent risks with this interpretation / approach because the government can care less about how anyone interprets the law; it has the final say in everything.  However, it sounds like the OP is only looking to do it as a side gig.  I cannot help but compare it to the people I know and “employ” in different capacities.  I pay my gardener cash for yard work.  I pay my barber cash (who is my neighbor and she transforms part of her garage into a salon) for haircut.  I pay my car mechanic friend cash for auto maintenance.  They all have regular jobs & incomes and receive cash from me for these “side gigs” / services they provide me.  Although I have never asked, I presume they don’t report (or at least under report) my cash payments.  Practically speaking, we are the only people on this planet who know the transactions happen.  Unless I snitch on them (and I have zero incentive or reason to), I don’t see how anyone or the IRS can find out.

Then we’ll come to this age-old debate: when dating someone, you inevitably have to spend money on your BF/GF, especially in a financially lopsided relationship.  Why is this monetary transaction not taxable then?  Some may even go as far as arguing that sex between a BF/GF is also indirectly and intrinsically monetized.  It entirely depends on how you define money and value.  I know this is a drastic and twisted view, but it seems like love/affection/commitment will turn the monetary transactions into tax-exempt earnings.

[Wings246]

I may be digressing.  This discussion highlights the hypocrisy of the US (and many other) government.  On the one hand, this line of work is not recognized / legalized / legitimized, but on the other hand, the monetary transactions involved are scrutinized and penalized if not reported according to the rule book.  Purely ridiculous.

[d.anders]

7 hours ago, Wings246 said:

Purely ridiculous.

No taxation system is perfect. That's where a good accountant comes in handy. However, concealing escort work in the U.S. is much easier than one might think. When tips became required reporting, my hairdresser husband stopped listing himself as hairdresser on his 1040. He was, in fact, much more than a freelance hairdresser, so he listed himself as designer. He never claimed his tip income, ever.

If you're lucky enough to have a self-employed cash business, you'd be insane to claim every dollar. Obviously, you need enough income to coincide with your business expenses, but if your job description happens to be consultant, the latitude on business expenses is quite broad. 

Personally, I don't think poor people should be paying any tax on their income, and by poor, I mean anyone earning less than $150,000 a year. But you do you.

[pubic_assistance]

8 minutes ago, d.anders said:

Personally, I don't think poor people should be paying any tax on their income, and by poor, I mean anyone earning less than $150,000 a year. But you do you.

As a matter of fact, this very point was recently proposed.

I completely agree with you. The minimum deduction hasn't been appropriately updated in decades . The original intention was that "wealth" would be taxed. And wealth was defined as income above and beyond what you needed to provide housing, food and clothing for your family. RIGHT NOW we are stripped of the ability to even HAVE a house, dine out or have a family.