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Will & Grace Faces Friends In The Battle Of The One-Off Lady Loves

It's Will & Grace's clumsy one-night stand Diane versus Rachel's sangria-soaked sorority sister Melissa on Friends!

In the '00s, one Oscar winner and one Oscar nominee -- Mira Sorvino and Winona Ryder -- guest-starred as two past Must See TV hookups. The former appeared on Will & Grace as Diane, Leo's ex-girlfriend and, coincidentally, the only woman Will's ever slept with; the latter as Rachel's sorority sister Melissa, whom Rachel made out with after too much sangria at a luau. Superficially well adjusted, Diane's Vogue editor and Melissa's real estate agent turned party planner -- seriously Melissa, get new business cards -- aren't doing great by the end of their respective episodes. Hung up on the ones that got away, let's see who's going to "win" this battle by being more compellingly pitiful.

Who's been left to her own devices longer?

Diane's introduced in the second episode of Season 6, "Last Ex In Brooklyn," as one of Leo's exes invited to Grace and Leo's first postmarital dinner party. Over the course of the evening, however, we discover there are more interesting events in her history: she's also the girl Grace has always been jealous of since finding out Will slept with her -- something we first heard about in Season 3's "Lows In The Mid-Eighties." (In that episode, Diane's also briefly seen in a flashback, played by an actor who's definitely not Mira Sorvino.) Poor Diane has no idea she's been an underlying source of tension between Will and Grace for years.

It's a tight race, but Diane beats Melissa's story in "The One With Rachel's Big Kiss" by a few years: Will and Diane met in the mid-'80s, and Melissa and Rachel met a few years later.

Winner: Diane.

Who does the crazier thing when she's first introduced?

Whereas Melissa bumps into Rachel at Central Perk and is gone too soon -- with plans to reappear at a dinner somewhere around the episode's midpoint -- Diane gets the better introduction, because the episode's dinner party setting allows more breathing room. That said, it doesn't take long for each contender to make a lasting impression about what kind of person she is or isn't.

See, Melissa's wandered into Central Perk looking for cigarettes, the implausible brand of which is Newport Lights. Marlboro Lights or Camel Lights, sure, okay, I can see it. But Newport Lights? No way do I believe she smokes those. That aside, Central Perk doesn't even sell cigarettes. Not that it matters, since she sends Gunther on a mission to a nearby place to go get them for her. Or rather, abandons the conversation when he gives her directions and leaves him standing there awkwardly with a $20, whereupon he decides to run this errand for her.

Diane starts out well enough, showing up with a bottle of wine and bantering with Grace and Leo. But freely giving Grace her Hermès Birkin bag because she gets "a lot of free swag" working at Vogue and wants Grace to like her is just plain crazy.

Winner: Diane.

Whose resurfacing has more impact?

Rachel's news is broken in two parts -- once when Melissa exits Central Perk and Monica alludes to there being more to their relationship, to which Ross quips that "that's two of [his] wives" and Joey starts foaming at the mouth. And later when Rachel shares the fact of her Melissa hookup with Phoebe, who doesn't believe it because Green's "vanilla."

So while the Friends play it straight (no pun intended), the same can't be said for the ones gathered in Brooklyn. Or, more specifically, for Grace who, after Jack connects the dots and reveals how Will and Diane know each other, grabs her chest and starts shouting "oh my god" on a loop before storming out of the room.

Winner: Diane.

Who plays it cooler?

Other than drinking eight gallons of wine, Diane really keeps it together as everyone around her fights with one another -- until she doesn't. Same for Melissa, who pretends Rachel's made the whole thing up and goes about business as usual -- until she doesn't.

Winner: Tie.

Who has the sadder visual?

Once Diane cracks, she admits not only that Will is the superior lover -- sorry, Leo -- but that their night together is the only time she's ever had an orgasm. It was a night of passion so intense she didn't even care that her hair was burning on Will's hot plate!

That combustion doesn't hold a candle to Melissa's, though; the wonderfully spacey Ryder ably sells her alternately sad and creepy story. Confessing her love for Rachel outside the restaurant, she claims she can still hear the sound of their coconut bras banging up against one another as they kissed, and that she also pictures Rachel's face whenever she's with her fiancé Alan.

Winner: Melissa.

Who has the sadder cab ride home?

After Rachel kisses Melissa outside the restaurant to prove a point to Phoebe, causing Melissa to spill the beans that she's in love with Rachel, things are pretty awkward for Melissa, especially because there's no closure. (Not that we'd expect any, but still.)

Diane at least gets kind words from Jack and Karen out of it. And, as an added bonus, the gift of Karen's dog Chompers...whom she plans on renaming Will. Yikes.

It's a tough call. Diane's probably the more screwed up of the two, but in terms of sad, awkward cab rides, I think Melissa has the edge. At least Diane has a dog to snuggle!

Winner: Melissa.


Characters aside, Ryder gives the better performance. Sorvino's great, but she starts to wobble a bit when asked to emote in the third act. But their episodes are equally strong: Friends has a great subplot about Chandler getting a tux for his wedding, though I'd give Will & Grace the edge because the whole episode's built around Diane and it's one of the show's absolute best.

So while it's a close one -- both women really seem to have been affected by their drunken hookups -- Diane's the clear winner...or rather, the loser. Congratulations?

Winner: Diane.