08/19/2010 12:22 pm ET | Updated May 25, 2011

Fifty First (J)Dates: The Perils of Video Chat

This story was graciously emailed to me by a Fifty First (J)Dates enthusiast. (You can contribute your own to!)

The parentheticals are yours-truly.

So I'm signing onto JDate to check out the latest messages in my Inbox when I get an IM from an Australian guy. (Girls are suckers for accents. The end. It shouldn't really matter that this creeporamalamadingdong is Australian, but like, you could look like a duck-billed platypus and have an Australian accent and I'd still mate with you.)

I check for the essentials: more than one good looking picture - check, height - (I know, im a little bit of a height snob) check, living in NY - check, normal description - check. So I figure I'll accept. (Being a height snob is acceptable, within reason. Granted, you're talking to a girl who solely wears sky-high shoes and has a balance problem, so I've just become accustomed to resembling a giraffe compared to my date. And giraffes are cute anyway.)

Early on he asks if we can speak on Skype instead - I agree and so we exchange Skype names. (Honey, this is a giant red flag. In my experience, half the time I'm being Skype-friended by a random man in Dubai who's told me that I'll win a million British pounds. Ever notice how those spam things aren't in USD? Like HELLO DEAD GIVEAWAY!)

He had just moved back to NYC after living in Australia for a while so even though I barely use it, I figure Skype must be his go-to way of talking to people. I sign on and see an incoming chat request and accept before I realize that it's a video request. (Skype can often be just voice, unless you're in a long-distance relationship a la Johnny Drama and try to make out across the screen.)

Ironically enough my first thought is, 'Does my hair look okay?' and my second is, 'Why the hell is he video chatting me??? I better not see anything gross..' (This is Chatroulette all over again. You're in for some wang!)

(I know, you're all thinking I should've ended this conversation the second I realized that this strange guy was video chatting me... But I have to admit, I was intrigued. And I have this naive philosophy that people on Jdate are just good people. And on top of that, I'm a sucker for Australian accents! Who isn't?) (In addition to swooning for duck-billed platypi with Australian accents, I often assume a nice accent means someone is smarter or more normal. Which is absurd. It really makes no sense, you could be talking about the morally inquisitive nature of bananas and if you're me you're sole arbiter of the Arab-Israeli Peace Process.)

And then, another surprise - I see my own image in the video reflection, but don't see his. I ask him why and he responds nonchalantly, "Oh, well my camera has been broken for a while." Why would he invite me to a video chat that only works one way? (At this point come onnnnn he definitely has his hands down his pantalones.)

Anyway, the first thing he tells me is that I'm very pretty.

(I know I'm pretty, thanks, I'm staring at myself in the video screen right now. And you know that on video chat you're not making eye contact anyway because you're staring at yourself and you're like oh crap my pores look awkwardly large at this angle let me also move the stuffed animals out of the camera range.

"NO MOM GO AWAY I'M BUSY VIDEO CHATTING." Parents on video chat is hilarious. They scream at the screen and don't understand what's going on. I spent an entire session in Argentina video-chatting with a potted plant because my mother didn't understand she had to look at the little square. I'm glad nothing wilted in my absence.)

Before I even get the chance to awkwardly thank him, he proceeds to tell me that he is a painter and asks me if I've ever been painted before. (What??) (Is this an homage to Titanic? This could potentially be romantic, you know, if you were Leonardo DiCaprio. Is it just me or is he starting to play the same slightly tortured but hot brooding psycho person in the last five films he's been in? Are we reinacting Titanic? Is there ice involved? NEVER LET GO JACK. OR IN THIS CASE, NEVER LET GO JONATHAN DAVID.)

I respond, definitely not.

He says that he would love to paint me, and sends me a link to his work. I hesitantly click the link and see an abstract landscape painting at the top, kind of impressed but still proceeding with caution.

And then I see it. The paintings of women.... from the waist up.... naked. (I'm not entirely sure why this is a surprise in any way, shape, or form. Maybe he's in his Skype Period, or participating in a series called "JDate, a View from the Knockers Up: The Wonder(bra) Years.")