A Date With The IRS

what's your price
OH my gosh this was too funny to pass up. And before you ask – yes, it’s real :) Here’s a clip from the email I got… way to capture my attention SpringWell Financial! (I know, this sounds like a paid advertisement but I assure you it’s not.  This is called clever marketing – you make me laugh and I want to share it with everyone! Haha… take note boring spammers.)

There’s a new site called WhatsYourPrice.com that offers a decidedly commercial twist on the age-old quest for true love. Their romantic slogan: “Buy a First Date With Anyone.” Generous daters (mostly men, of course), post what they’re willing to pay for a date. Attractive daters (mostly women), post what they want to get for a date. As one woman from the site said,

“If it’s going to be a big, huge waste of time, at least I’m going to get paid for it… A lot of these guys are wealthy gentlemen, and I think my time is as valuable as their time.”

Guys, your friends might snicker if they find you paying for dates. Ladies, you probably wouldn’t want to tell your mother. But forget what your friends and family think. What does the IRS think of getting paid to date?

Let’s say a generous gentleman pays $100 for a date. That $100, given in exchange for his date’s time, company, and conversation, is clearly taxable income to her, reportable as “Other income” on Line 21 of her Form 1040. (Taken to its logical extreme, generous gentlemen ought to be issuing 1099s for dating over $600!)

Now, what about the value of dinner? Is it additional compensation for the date? Presumably, a generous gentleman wants to impress his date with more than just coffee at Starbucks. Internal Revenue Code Section 83 states that property transferred in connection with services is taxable at its fair market value. Fortunately, daters can pay the actual tax in cash – otherwise, they might have to bring doggie bags for the IRS. (What sounds like the right tax for dinner at a nice steakhouse, anyway? Three bites of filet and half of a baked potato?)

And what about the generous gentlemen? Are there any deductions available for them? Maybe, if they take their date to a business function. Otherwise, no dice – and the gifts aren’t “charitable contributions,” either, unless the date is a “registered nonprofit.”

At first glance, taxing daters might not seem like a “10” on the IRS’s priority list. But WhatsYourPrice.com boasts 50,000 members and says the average bid for a date is $138! That suggests there’s a fair amount of tax revenue worth chasing. Of course, there would be certain challenges collecting that revenue. It’s bad enough when gossipy co-workers and nosy family members poke their nose in your love life. Who needs an IRS auditor tagging along on a date?

In all seriousness, the internet really is changing how taxes work. Take sales taxes, for example – state governments would love to collect sales taxes from online retailers, and several have taken aim at Amazon.com. But online daters, you’re still safe – at least for now – and we’ll be sure to let you know if that changes!

Who knew taxes could be so entertaining! :) What do you guys think about this? Could you see yourself ever paying for a date? (Feel free to comment anonymously if you’d rather not put your name, haha…)  I’d probably try it just so I could blog about it and see what it was like if I weren’t married, but all in all I must say it’s pretty damn clever.  And with 100,000 members now (they just updated their blog) I’d say it’s a success!

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  1. Matt June 30, 2011 at 7:19 AM

    I think I’ve heard of this service before They have field reps on the corners and in the alleys downtown :)

  2. No Debt MBA June 30, 2011 at 7:53 AM

    I’m just wishing I’d thought of it as a business idea and could take a 10% cut. If the average member goes on three dates that would be around $2 million.

  3. jerichohill June 30, 2011 at 8:04 AM

    100K members? Most are inactive or dudes.
    I don’t see this dating site lasting

  4. cashflowmantra June 30, 2011 at 8:10 AM

    Being married means paying constantly in more ways than one. Interesting site concept.

  5. Shawn June 30, 2011 at 8:55 AM

    Sooooo if the date ends in “sexy time” does it now count as prostitution? ;)

    Pay for a dating service? Sure.
    Pay someone specifically for a date? Nope, that just screams “crazy”

  6. Melissa June 30, 2011 at 10:05 AM

    Do people actually have to issue some sort of form for all transactions over $600? Really? In Canada, as far as I know, we have none of that. If you’re an independent contractor, you could take a $20,000 date and it’s just up to you to report that income to the government come tax time. Interesting!

  7. Kevin June 30, 2011 at 10:41 AM

    Being a guy we end up paying how ever ya look at it. But what gets me is isn’t this LEGAL PROSTITUTION? I mean your paying for The unworthy or corrupt use of one’s talents for the sake of personal or financial gain.

    Maybe I’m just upset that I didn’t think of this idea and I’m not reaping in some cut of the (pay to date) profits.

    Time to get on the ole thinking cap and a 30rack of beer and get some idea’s to paper.

  8. Crystal June 30, 2011 at 11:05 AM

    Nope. Uh-uh. No way.

    First, if I ever did want to start dating for money, $100 for the evening and a filet mignon wouldn’t cut it (sorry, but I’d be a high class hooker if that was ever the line of work I pursue). Second, if you have to pay to get a date, you are not my type. Third, my husband would probably not look at this as my best income source idea ever… ;-)

  9. Harri @ TotallyMoney June 30, 2011 at 11:37 AM

    WHAT?! WOW. Echoing Crystal’s sentiments here. Absolutely not!

    Couldn’t imagine anything much more degrading than being paid to date. Oh wait, yes I can, paying someone to date you. Can’t believe it’s so popular!

  10. Kathy June 30, 2011 at 12:08 PM

    @Matt…roflmao! snort, snort!

    Just when I think I’ve heard it all, something like this come out of left field & slaps me upside the head.

    I’m NOT going to get on my moral soapbox here….just, suffice it to say that it’s nothing I would like to associate myself with.

  11. Jason@LiveRealNow June 30, 2011 at 1:05 PM

    It’s only prostitution if sex is included. Less than that, it’s an escort service, with just a hint of paid sex.

  12. J. Money June 30, 2011 at 1:19 PM

    What? No takers yet? I KNOW some of y’all would def. give this a shot – don’t hide ;) I’d even be willing to pay someone to try this out if i can find some extra funding! How about that for a guest post?? Or better yet – a Side Hustle! Haha…

    @Matt – Haha… they serve food there? :)
    @No Debt MBA – There’s a nich for everything! Maybe you can start a dating site for less-than-pretty people? :)
    @jerichohill – Maybe not, but they hit 100k in like 4 months. That’s insane.
    @cashflowmantra – Haha… I’m not touching that one.
    @Shawn – Interesting thought! I’d say no to prostitution though. Getting someone to dinner is one thing, but the festivities afterward are zero going into it. BUT, and I’m sure this is happening allll the time, I bet the guys would then offer to pay for the after-party ;) So it would be two transactions, the first legit, the second not so much. And odds are pretty high the 2nd is possible if they’re only into it for money. But who knows – people have met in stranger ways.
    @Melissa – Yeah, it sucks. But I mean you can kinda understand it. People are always trying to slip things by the gov’t and not pay their portion due, so the $600 at least sets some sort of bar. Usually money that much or higher means someone’s doing some hustlin’ ;)
    @Kevin – Hahaha yes to getting your thinking beers on! But prostitution? There’s no mention of sex good sir, just a date. Of course that can all lead to sex and further monetary transactions, but legally it should all check out in my opinion.
    @Crystal – Haha…. but what if you’re a workaholic and are tired of dealing w/ jokers? I can get the whole “time is precious” part, though I don’t know how safe it is really for everyone involved. I’d be freaked out if I was a lady, I can tell you that.
    @Harri @ TotallyMoney – Haha…. that’s the land of the free for ya :) we can all do whatever we want as long as it’s legal! I’m okay with two parties doing anything if it’s consentual on both sides.
    @Kathy – That’s fair :) It takes all types!
    @Jason@LiveRealNow – Yep, agreed.

  13. Crystal June 30, 2011 at 1:54 PM

    @J Money, to be serious, if my husband was abducted by aliens and I was in the market again, if I couldn’t meet someone through one of my hobbies, then I’d join eHarmony before ever getting paid to date. When money is so callously involved, I doubt a real connection can be made. And I don’t date frivolously – why waste time on something that isn’t a real connection?

  14. Jen @ Master the Art of Saving June 30, 2011 at 2:07 PM

    I know this sounds bad, but if I wasn’t married, I’d totally do this. There is no way in h*ll my honey would let me do this now. Going out on dates instead of going to work—how could I pass that up? Obviously I wouldn’t DO them or anything like that. Still, what a fun way to earn money.

  15. Crystal June 30, 2011 at 2:26 PM

    @Jen, only if the guys weren’t creepy, offensive, smelly, or the many other bad things that they could be, right?

  16. jesinalbuquerque June 30, 2011 at 2:27 PM

    This has been around for quite some time. In fact, it’s called the world’s oldest profession. “Escort services” making prostitution. Not that I have anything against it — I think prostitution should be legal. But I am amused by the elaborate attempts to camouflage what’s going on.

  17. Jen @ Master the Art of Saving June 30, 2011 at 2:51 PM

    @Crystal- I could deal w/ creepy, offensive and smelly (I’d just charge more, hehe) but psycho I’m not cool with. You wouldn’t really know until u were there though, I’m pretty good at holding my own but I’d still keep in public. Not gonna happen anyways, but I’m sure I could kick some decent @ss. :-)

  18. Jenny~Z June 30, 2011 at 3:05 PM

    I’d do it.. but I’m a girl so I’d (hopefully) be on the receiving end of the date! hahah.. this is very entertaining :D

  19. Crystal June 30, 2011 at 3:37 PM

    @Jen, LOL. I’m a wussy with a big mouth, so I could talk big and then lose fast…

  20. MAH June 30, 2011 at 3:46 PM

    Interesting concept. Sounds like dating site meets escort service to me. I am sure the stories that result from using or knowing someone who uses the site are even more interesting than the concept.

  21. Suba June 30, 2011 at 6:21 PM

    100k members? I wish I thought of an idea like this. Escort service with a politically correct name…

    But seriously it would scare the hell of out me. What exactly is that guy expecting for that $100? Why can’t he get a date without paying for it? I have watched enough Law & Order – SVU episodes to imagine all kind of worst situation and freak out :)

  22. Jenna, Adaptu Community Manager June 30, 2011 at 7:49 PM

    Don’t all match maker sites have to pay taxes, why would this be any different?

  23. J. Money June 30, 2011 at 10:31 PM

    @Crystal – Haha, will make a note of it ;)
    @Jen @ Master the Art of Saving – Yeah, no place here for Psychos. Or Sociopaths for that matter, that’s worse!
    @jesinalbuquerque – Haha, I’m still going to claim naivety and believe they’re just going on dates :) Maybe you should go undercover and then write about your findings? ;)
    @Jenny~Z – Haha, you sure would!
    @MAH – I know, right? I REALLY hope someone tells us they’ve tried it before so we can get the inside scoop… I’d be VERY interested in finding out!
    @Suba – Haha… well that’s easy – a HOT date. Any of us can get dates if we really wanted to, but a sexy one? Like, REALLY sexy one?? I don’t think we’re that good ;) So for $100 you get to share your date with a hottie. Who likes you for your money :)
    @Jenna, Adaptu Community Manager – It’s the women receiving the money that’s in question, not the site. If you make $600+ by going on dates you’re technically supposed to claim it. Well, if it all comes from one person I believe.

  24. Financial Samurai July 1, 2011 at 11:51 AM

    Love the idea and thanks for sharing!

    If I was an attractive unemployed women getting paid $200 a date and getting free food, I would be a full-time dater! lol

  25. J. Money July 1, 2011 at 12:45 PM

    haha… it’s a good ROI isn’t it? :)

  26. Joy December 8, 2015 at 7:36 AM

    Let me just tell you all something. Fun fact… Generous dates have paid up to$100- $400 to buy me dinner at Capital grill in dc. Just dinner.
    I also date on ” traditional ” websites. The quality of the men are much better on Wyp. And they get dates. They don’t get lost in the masses of “frogs” out there. They aren’t “losers” at all. They are intelligent, successful men. Who are dating beautiful girls. Are you?

    1. J. Money December 10, 2015 at 6:40 AM


      I’m no longer in the dating pool anymore, but I was fortunate to marry a beautiful woman :)