As a single Orthodox Jewish male, my dating pool consists of all the single Orthodox Jewish women in the world, or .000001% of the human population. (A number which drops by a factor of ten with each year I age.) These grim statistics could really throw a guy. After all, where am I going to meet this .000001% of the human population? Should I introduce myself to 1,000,000 women at bars, one of whom statistically would turn out to be an eligible Orthodox Jewish woman? No, there is a better answer: – Cyberspace, where you don't have to buy anybody drinks. Online, there are a variety of Jewish chatrooms frequented by Orthodox women. But there are many halachic and moral potholes for the single Orthodox Jew looking for his mate in cyberspace, so I therefore offer the following guidance . . .

The Jewish man searching for his mate in cyberspace will quickly discover that there are many non-Jewish women seeking Jewish mates in cyberspace. This is particularly inevitable if you have an online profile mentioning the J-word. I am continually bombarded with E-mails and instant messages on America Online by non-Jewish women who want to bring me home to their families, some of which live thousands of miles away and engage in idol worship. The fact that these women are not Jewish is not always apparent at first; some of them know more about Jewish culture than a lot of Jews, or at least those Jews who haven't seen "Blazing Saddles." Why, you ask, do non-Jewish women think Jewish men will be good mates? I am not sure. Perhaps it is the plethora of wonderful male Jewish role models we have in society. Think about it – there's Woody Allen, Marv Albert, and United States Secretary of State Madeline Albright – and that's just the A's!

Once you have established that someone is Jewish, it's much easier to determine whether she is religiously observant. You simply ask the question "Are you frum?" If she is frum, you will get a response like "modern orthodox, and you?" or "I'm a nice yeshivish girl who hangs out in America Online chat rooms with people named Sexxxyyid, and you?" If the person is not religious, she will respond "Pittsburgh, and I don't date guys who can't spell!"

Cybersex is what happens when two people start exchanging involving sexual fantasies to each other online. Sorry, that's detention. But seriously, here is what a "normal" cybersex session might look like (you may not want your children to read this, unless they have already seen the Starr Report):
[Cybergal101] OK, so we're all alone, and I show you my entire software collection.
[Cybergeek] You sure know how to spin a guy's hard drive!
[Cybergal101] Before we go any further, do you have virus protection software?

This type of banter presents obvious halachic difficulties. It is simply improper to discuss sexual matters with a member of the opposite sex to whom you are not married. Therefore, I have developed something called "Shomer Negiah cybersex" to allow observant Jews to join in the excitement of cybersex without violating Jewish law.
The laws of " negiah" forbid any sexual touching between unmarried members of the opposite sex. True, all cybersex is technically shomer negiah, but in "shomer negiah cybersex", you don't even fantasize about touching the other person. Here's a sampling of my shomer negiah cybersex routine:
[Jew123] OK, so you're wearing an oversized sweater, a long dark skirt, black bulletproof stockings, and tennis shoes . . .
[Jew123] I try to undress you with my eyes . . .
[Jew123] But I can't because you're wearing too many clothes.
[Jew123] Then suddenly . . .
[Jew123] My eyes fall on your bare . . .
[Jew123] naked . . .
[Jew123] sexy . . .
[Jew123] wrists.
I have managed to seduce countless observant women online with these words, some of whom even suggested we do Hoshanos together.


Beyond determining whether your new online friend is Jewish and how religious she is, perhaps the hardest thing to figure out is whether indeed she is a she. Several years ago, I was living on Manhattan's Upper West Side and, as was my habit when I had a large paper due for law school the next morning, I spent all night socializing in one of America Online's Jewish chat rooms. Suddenly, I received a message from someone. We began to talk. She had every trait I have ever wanted in a woman. It was as though I had sat down and spent hours telling someone what I was looking for, and then suddenly, poof, she appeared. And that is precisely what happened. You see, I finally worked up my courage and asked if I could call her. "No," she typed, "I'll call you." So I gave her my number. Then "she" called. "She" was my male roommate on the other side of the three inch wall behind my computer monitor, who online became my ideal woman. I was very upset, because this was a breach of trust by a friend, a nasty joke, and violated quite a few halachas. Also, I felt somewhat emasculated. At this point I became very angry and violated a few more halachas myself when I lifted him up, through him out of our tenth floor window, and laughed as he fell screaming to his death. I am only kidding, of course. I was not laughing at the time.

America Online and most Internet chat services have a handy feature called "private rooms" where you can speak one on one with another person in a "room" where noone else can see your conversation, except Bill Gates.
I met a woman in an AOL chatroom recently, however, and was alerted to a halachic problem with these "private rooms." To illustrate what I am talking about, I will reprint the relevant conversation which occurred after I invited her into a private room:
[Frumchick101] I thought you said you were frum!
[Jew123] I am!
[Frumchick101] Well, don't you see a halachic problem with this?
[Jew123] Did someone forget to put a mezuza on the door?
[Frumchick101] No, dummy.
[Jew123] So what's the problem?
[Frumchick101] Yichud.
Yichud is the area of Jewish law forbidding a man and a woman who are not married to each other from being alone in a private space, such as the Oval Office.
To avoid yichud problems in cyberspace, give your private room a name which 15,000 other people have already thought of, so you can expect some weirdo to pop in at any time, making it something less than private.
Or just ask your roommate to join the fun.

Finally, any Jewish traveler in cyberspace should be equipped with the tools necessary to communicate Jewish concepts in a concise manner so as to prevent carpal tunnel syndrome. In the secular cyberspace universe, "emoticons" are used for this purpose. Emoticons are brilliant creations which convey complex, subtle emotions with simple keyboard characters. For example: : ) = happy
: ( = sad
: B = needs dental work

As Jews, we need our own set of emoticons to transmit the vast array of concepts inherent in Jewish culture. I have therefore created the following extremely useful emoticons:
(: ) = man happy to be wearing a yarmulka (ok, I will be a politically correct pluralist, it could also be a Reform Rabbi)
((: ) = man with two yarmulkas
): ) = man with yarmulka on upside down
{: ) = man with one of those yarmulkas that you find in the bin outside Reform and Conservative sanctuaries with the pointy thing on top
*: ) = Yeshiva High School student who thinks he is cool because he is wearing a small yarmulka
hanging over his ear
: ) = man with a backslash for a yarmulka
C:: ) = man with a DOS prompt for a yarmulka

(For some other bangitout emoticons click here) I hope that this guide has been helpful for Orthodox singles in cyberspace. And if it offended anyone, my old roommate wrote it.

Happy surfing.