A Date With the IRS

The internet has transformed so much of how we live our lives. We find our news online, find books and music online, and find travel bargains online. The internet has even transformed how many of us find romance, with a dizzying range of sites for suitors of all interests. Match.com advertises that one out of five relationships now begins on an online dating site. EHarmony ads feature smiling couples, married after meeting online. And let’s not forget the raft of specialized dating sites like dateHarvardSquare.com (free for Harvard students and alumni), VeggieConnection.com (for those who won’t be ordering steak on their date), and WeWaited.com (for those who won’t be getting lucky on their date). What would Yente, the village matchmaker from Fiddler on the Roof, think of JDate.com for Jewish singles?
Now 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!