What Was Bill Gates and an Ann Winblad's Relationship?

When I first found out that Mr. and Mrs. Bill Gates would be divorcing after 27 years of marriage earlier this week, I thought immediately of Holly Golightly — the classic American gold-digger immortalized by Audrey Hepburn in the admittedly loose but arguably more famous film adaptation of Truman Capote’s 1958 novella, Breakfast at Tiffany’s. In the film, Holly maintains a constantly updated list of the richest men in America under 50, which always struck me as a particularly impressive feat in the pre-internet era. While Bill Gates would have exceeded Holly’s desired age range, I imagine she probably would’ve made an exception for a potential suitor of Gates’ fame and net worth, and I could picture her immediately setting to work figuring out how to scheme her way into his social circle, seeking more than just $50 for the powder room.

Like young, aspiring Holly Golightlys everywhere, my own immediate response to the Gates divorce was, “Bill Gates is single,” and then to Google his net worth. It’s a gold-digger reflex — genetic, probably. We know we aren’t going to be the new Mrs. Bill Gates, but we can’t help but at least consider the possibility. Even if we did have a shot, however, it turns out we’d still have to get through one final boss: Bill Gate’s ex-girlfriend, software engineer and venture capitalist Ann Winblad.

According to a recently resurfaced Time profile on Gates from 1997, Winblad was an ex Gates dated before his marriage to Melinda, though the exes maintained a close friendship. So close, in fact, that in addition to asking Winblad for her blessing to marry Melinda, Gates also maintained an “arrangement” with Winblad even after the 1994 marriage, in which the pair would spend an annual weekend together at Winblad’s beach cottage on the Outer Banks of North Carolina every spring.

This may sound steamy — and also like the plot of a Nicholas Sparks novel — but Gates has a way of making it sound a lot less like a sexy weekend getaway than summer camp for science nerds. According to the 1997 interview, the ex-lovers spent their weekends together riding dune buggies, hang-gliding and playing “putt-putt while discussing biotechnology.” Sometimes, Gates said, they would “marvel about how, as two young overachievers, we began a great adventure on the fringes of a little-known industry and it landed us at the center of an amazing universe.”

While Melinda was apparently aware of and cool with this little tradition, it remains unclear whether it continued after 1997, or, more importantly, whether the “arrangement” included sex. Did Gates get a hall pass to sleep with his ex every year? Have he and Winblad secretly still been in love all these years? In a Nicholas Sparks book they definitely would be.

Anyway, dating Bill Gates sounds super boring and also I don’t want to have to go through Ann Winblad, who seems like a very formidable gatekeeper (“Gates”-keeper?). Thus, I’m afraid I will be removing myself from the race to be the next bride of Microsoft in order to focus on my original goal of becoming Jeff Bezos’ next ex-wife. Best of luck to the rest of you, though.