Politics as usual? Not quite. The Bay State may be known for its liberalism, but that hasn’t kept old-style gender issues out of the race. O’Brien has tried to avoid the subject during this close campaign, focusing instead on her record as state treasurer. But Romney, the buff, telegenic hero who organized the 2002 Salt Lake City Olympics, has to navigate more carefully through these tricky shoals. He needs to win over women voters, whose support in the ’90s was crucial in electing Republican Gov. William Weld and re-electing Democratic Sens. Edward Kennedy and John Kerry. The problem: how to do so without appearing patronizing or playing into stereotypes.

Romney’s handlers are particularly sensitive to the difficulties. The candidate’s chief adviser is Michael Murphy, who was lead strategist for Rick Lazio during the Republican’s infamous in-her-face lectern encounter with Hillary Clinton during a debate in the New York Senate race two years ago. Undoubtedly with that in mind, Murphy’s charge has been careful to maintain an arms-length approach to his rival in this race.

The efforts to present Romney as stoic, demure and gallant, however, have had limited success. “Every woman–liberal, conservative, Republican, Libertarian, Democrat or Green–knows what it feels like to be run over by a man with Romney’s air of entitlement,” wrote Boston Globe columnist Eileen McNamara after Romney likened O’Brien to Massachusetts Acting Gov. Jane Swift in a morning radio interview.

Swift, a Republican, is widely regarded as a political lightweight. And Romney was not necessarily aiming his barb at Swift’s gender: he had also been trying to suggest that he–an outsider who has never held elected office–was better equipped to bring change than O’Brien and Swift, both career State House insiders. But for many women, including O’Brien, the inference seemed unavoidable. “I think it’s dangerously close to implying that all girls are alike,” O’Brien told reporters.

Not surprisingly, Romney denies any gender gap. “I have no problem connecting with women,” he told reporters after the Boston Club event. Nonetheless, a recent Boston Globe poll showed Romney, while even in the race, trailed with women voters by 18 points. As in his 1994 race against Kennedy–where women voted against Romney by a margin of nearly 2 to 1–the GOP candidate was supported by the majority of men.

Why has Romney emerged as such a lightning rod on the subject of women? Perhaps it’s because he muscled out Swift, who tearfully withdrew from the race in February to avoid a costly–and futile–Republican primary race against the successful venture capitalist. Perhaps it’s his being named one of the world’s 50 “most beautiful people” by People Magazine. Perhaps it’s the television ads that show him bare-chested in a swim suit–ads that prompted Democratic Party spokeswoman Sue Harvey to ask whether Romney were running for governor or prom king.

But perhaps Romney may just be reaping an unfortunate legacy. Perhaps it’s also because women have long been fighting against a glass ceiling in Massachusetts politics. The state is one of the few that has no women in Congress and traditionally has been home to a disproportionately low percentage of female state legislators.

O’Brien is the first woman to win her party’s gubernatorial nomination in the state. (Swift moved into the position because she was lieutenant governor when Gov. Paul Cellucci accepted the post of U.S. ambassador to Canada.) And O’Brien did it as the sole woman in a four-way race that included Bill Clinton’s former secretary of Labor, Robert Reich; State Senate president Tom Birmingham and former state representative and senator Warren Tolman. Ironically, Romney now finds the glass slipper on the other foot: he is the lone male facing off against four women: O’Brien, Libertarian candidate Carla Howell, Green Party candidate Jill Stein and independent candidate Barbara Johnson.

Inevitably, the Mars-Venus debate has obscured the substance of the contenders. Each has ivy on their resume: O’Brien did her undergraduate work–and captained the varsity women’s soccer team–at Yale. Romney took an M.B.A. and law degree at Harvard. Both come from political families: Romney is the son of former three-time Michigan governor (and onetime Republican presidential contender) George Romney. O’Brien’s father Edward is a member of the Massachusetts Governor’s Council, the board that approves the chief executive’s judicial nominations.

Both also have hairstyles that can endure gale-force winds. But the similarities end there. O’Brien, 42, is a career politician who has spent most of the last 16 years under the Golden Dome in the Massachusetts State House. Romney, 55, admits he doesn’t even know where to find the men’s room there. O’Brien looks for battles she can win; Romney speaks of vision and new leadership.

Each candidate has negative stereotypes to sidestep. While Massachusetts is a Democratic state, the GOP has held the governor’s office for 12 years. Many voters, including Democrats, have opted for Republican governors to counter a Democrat-dominated legislature that is largely run like an old boys’ club. It is important for O’Brien, who was a legislator for eight years and whose father is a Beacon Hill insider, not to be perceived as part of that club.

Romney, believed to have national aspirations, doesn’t want to be seen as part of the club of Republicans who left the job midterm to seek other employment–a course followed by the last two elected GOP governors. Most significantly, the two differ on their strategy to revive their state’s moribund economy. Massachusetts has racked up 20 consecutive months of job losses. Unemployment, while still below the national average, hit 5.2 percent here in August. The economic boom of the ’90s is now a sad mirage. O’Brien promises to focus on helping smaller, homegrown firms prosper; Romney wants to create a more inviting–read less regulated and onerous–climate for businesses considering relocating to the Bay State.

The two differ in style as well. Romney, the outsider, offers broad iconic bites of what he calls “vision.” O’Brien responds to questions with pragmatic, narrowly focused anecdotes mined from her years in government. With Romney slipping from his early front-runner status, his camp promised that their man would come out swinging in the remaining debates before the Nov. 5 election. Indeed, Romney did take a tougher line during a second debate this week. He looked O’Brien in the eye, attacked her record on taxes and revenues and even addressed her by name. O’Brien tried her best to counter, chiding him for breaking his promise not to run a nasty campaign. “Come, come, Shannon,” replied Romney, folding his arms and chuckling like an amused-but-stern parent. “There’s no place for whining in politics.” Did women approve of Romney loosening his velvet gloves? Both Republicans and Democrats claimed a debate victory–but commentators declared it a draw.