Here's how it works: Schmidt is an angel investor in Giiv, a Web service for sending gifts via cell phone that recently raised $2.3 million. Schmidt invested his money through TomorrowVentures LLC, a venture capital fund of which Court Coursey is managing director. Court Coursey is a 36-year old entrepreneur, investor — and "dear friend" to Bohner, according to her website.

None of which is to say Schmidt is back with video producer Bohner; there's no telling when he committed the money (his investment was announced in July), whether he met Coursey through Bohner or vice versa, or whether it's all one big coincidence. But connecting the dots is certainly fun. Let us know if you have more clues.

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Our spies in 2006 told us Schmidt spent time on Fire Island, where Simon has a house, the year before; later in summer 2006 the New York Post reported a sighting of Schmidt leaving the restaurant Island Mermaid there with actor Stanley Tucci. By the end of 2007, the couple had broken up amid talk Schmidt was also seeing Kate Bohner, the business writer.

But now one tipster, a self-described friend of Bohner's, tells us that relationship is finished (commitment issues), while another says Schmidt visited Simon's place on Fire Island "a few times" last month. Meanwhile, the married CEO still hasn't divorced his wife. For all this cycling through old flames, one hopes Schmidt's vacations at least involve new restaurants.

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(Pic: Dave McClure)

Google doesn't have its own corporate jets — good thing, since that transportation perk is so déclassé these days. Instead, the company leases planes, including a set of jets jointly owned by Schmidt and Google cofounders Larry Page and Sergey Brin. Peter Kafka at MediaMemo notes that Google paid for $106,201 worth of travel to have Schmidt's "family and friends" accompany him on business trips.

Which made us think: What happened in Schmidt's life last year? Schmidt, who is married, has had a series of girlfriends on the side. (Good for him!) But he started getting serious with his most recent one, Kate Bohner, in late 2007. Bohner, who was briefly married to author Michael Lewis and is said to have inspired the character of sex-crazed Samantha on Sex and the City, lived in south Florida until she relocated to Los Angeles last fall. During the presidential campaign, she was spotted escorting Schmidt to at least one YouTube-sponsored debate.

I asked a Google spokesman if Bohner was one of Schmidt's passengers, but he declined to comment. So did Bohner fly free on the Google party plane? If so, good for Schmidt: Not every executive, in this perk-hostile times, gets to fly such friendly skies.

Bohner, a former journalist and TV personality who was once briefly married to author Michael Lewis, took up with the married Schmidt last year while she was living and working in south Florida. Since then, Schmidt "paid her an ungodly amount of money" to relocate her business, Kate Bohner Productions, to Los Angeles; she set up shop on Pacific Avenue in Venice, Calif. He's been spending the occasional weekend with her, flying down from the Bay Area on Thursday and leaving Saturday, staying at the Beverly Hills Hotel. (Schmidt saw her twice in October and at least once in November.)

But besides paying for the move and buying Bohner a new set of diamond earrings on every trip, Schmidt, whose net worth has been estimated at $6 billion, hasn't been forthcoming with cash. He attended a meeting at Bohner's firm to get pitched on funding a new $1 million documentary show. It sounds like he didn't bite, because Bohner's said to be losing her job.

Will Schmidt set Bohner up with a job at Google, as he did with a previous girlfriend, PR exec Marcy Simon? Bohner has told people she's already been working for Google — for free. She's been writing executive summaries about Google's push into the cell-phone market, work she estimates she could have billed at $250,000.

So why is Schmidt being so cheap? It's possible he's nervous about bad publicity that could come from leaving a money trail. He's said to have an arrangement with his wife Wendy, but she may not appreciate having the name of Schmidt's girlfriend make the headlines. So why doesn't he buddy up with some other media mogul and get them to fund Bohner's company on the sly? Ah, there's the rub: Schmidt has been so aggressively unlikeable in his dealings with other media CEOs that he doesn't have any chits to cash in.

It's not the fact that the married Schmidt sleeps around that bothers Schrage (and most of his underlings in Google PR); it's how Schmidt mixes business and pleasure. His recent mistress, Marcy Simon, was temporarily installed in Google's New York office to head up PR for Google's still-nonexistent Googlephone. Simon's replacement, TV journalist Kate Bohner, has squired Schmidt, very publicly, to at least one political debate cosponsored by Google's YouTube and CNN. If Schrage wanted to deal with bimbo eruptions, he could have stayed in politics.

It's not clear Schrage is the best choice for the Facebook job, objectively speaking. One person who's worked with him says he's a disaster as a manager, and not particularly strong in the PR part of his duties, preferring the more high-falutin' policy work.

But that could make him the perfect yes-man to Facebook CEO Mark Zuckerberg's plans for world amelioration. At the South by Southwest conference, Zuckerberg talked, tongue not at all in cheek, about how Facebook could bring peace to the Middle East by preventing Arab teenages from turning into terrorists. He seems to believe sincerely in this stuff. And if it gets him a job at Facebook, Schrage is just slick enough to put on the illustion that he does, too.

In her little-watched "Watercooler Diaries" series on YouTube, Bohner films herself in a bikini, swimming with dolphins and interviewing Florida locals. In an on-camera commentary, Bohner makes the following observation about the dolphins:

The boys stay together in their bachelor pads to go hunter-gathering and also ... to go sniffing out for more pods of girls. Rrnnnggh! Just like human boys!

Well, Google shareholders can rest easy. Simon figured out that despite the massive diamond ring he gave her, Schmidt wasn't serious about promises he made Simon about splitting with Wendy. (According to a Simon confidante, Schmidt claimed he was "legally separated" from his wife. Can anyone confirm that?) "When he's with Wendy, he's completely with her," says an insider. And when he's not with her, he's with someone like Kate Bohner. Impressive that he manages to have so much free time while ostensibly running Google.