The scary part about taking your sex-tech project to the mainstream is that on the long, hard journey from quirky to safe, you risk wrecking the very thing that made you special.

Then, when the Bowdlerized version doesn’t do well, the backlash affects everyone in the sex-tech space, not just the particular application or product. “See?” say the analysts and the venture capitalists and the advertisers. “That’s why we don’t back sex things.”

Then when there’s a new sex thing they cautiously express interest about, the developers bend over backwards to show how nonthreatening and comfortable it really is.

Ah, the cycle of romantic startups.

Two years ago, I gave “relationships-management software” Girlfriend X a cautious thumbs-up. Now I’m bummed I can’t do the same for its latest incarnation, or for the beta version of its sister site, Boyfriend X.

The genius of the original Girlfriend X and its companion PDA app (”GFX Wingman”) was that it indulged in so-impolitic-it-must-be-true irreverence. Marketed as a dating solution for men, it took all those things that women naturally do in our heads and turned it into a database-driven toolset for players — or those who wanted to play at playering.

For example, its Yield Generator module plotted how much money you spent against how much sex you got, presenting you with a nice cost-per-hookup graph. Other modules sent automated love notes to the right woman at the right time, tracked anniversaries and other milestones for ongoing arrangements, and suggested hundreds of (terrible) pickup lines whose very awfulness could serve to break the ice with new prospects.

After that column came out, Sex Drive readers inundated the developers with e-mail — at least half a dozen requests, says founder Rick Hoxie — for a similar application for women.

Because yeah, we’re good at keeping this stuff in our heads, but parallel dating — sleeping with more than one person on a regular basis, without those people knowing any details other than, “I’m seeing other people” — can get complex to keep up with if you do it for more than a month or two.

Unfortunately, Boyfriend X lacks the rueful humor of the early Girlfriend X, managing to be bland and insulting at the same time. (The first question in the Boyfriend X FAQ is “What if I’m not smart enough to get this all working?”) And Girlfriend X was neutered on its way from stand-alone software to web-based portal.

Hoxie says they wanted to get more serious and to make a sort of “one-stop shop” for relationship management, blending a niche contact manager with a content-driven site.

In other words, there’s no Put Out Calculator for Boyfriend X that compares how many bases you’ve let him touch to how much money he’s spent on you, then recommends what you could hold out for next.

The watered-down Girlfriend X is still about creating bad boys out of nice guys, in their minds if not in their actions. But then Boyfriend X warns women to stay away from bad boys and find nice guys.

It may be what the moneymen believe the masses want (without the taint of associating with porn), but it also turns off the very people who might have used the racier version.

No wonder the sex-positive movement despairs of the mainstream.

Girlfriend X and Boyfriend X do have their redeeming qualities. It is handy to have access to dozens of dating and networking sites from one page, and it’s great to be able to search all of the reviewed profiles at once regardless of their site of origin.

Both services encourage members to rate people’s online dating and social networking profiles (he’s short! she’s fat! he’s married! she’s psycho!) and to post positive testimonials for friends and dates. Both provide detailed tracking mechanisms where you can store details about each person and every interaction you’ve had.

The mashups Hoxie plans in the coming months are definitely cool. One compares a person’s interests with a local events calendar and the weather forecast, then generates a list of targeted date ideas. Another sifts through the headlines to keep you apprised of current affairs relating to your prospect’s interests, so you always have something to talk about.

If they manage to automate more of the data entry — perhaps an import function so you can bring profile information into your contact manager with a single click — then X will mark the spot indeed, and the convenience will more than make up for the loss of personality.

I guess I’ll have to track my own blow-job-to-oil-change ratio from now on.

See you in a fortnight,

Regina Lynn

Regina Lynn is the author of Sexier Sex: Lessons from the Brave New Sexual Frontier.

Wired.com