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The Ultimate Will & Grace Ranking Of Grace Adler's Love Life

Grace dated some great guys and some total tools. It's high time we definitively, scientifically ranked them.

I think we can all agree that there is a little Grace Adler in each of us. We're all just flighty, redheaded twenty-somethings, living with our gay best friends in fabulous apartments in New York, trying to find love. But what does love look like when you're Grace Adler? Is it a greeting card writer who wanders into your studio when you're having a crappy Valentine's Day? Is it a crystal-toting hippie who treats you like a goddess and comforts you during menses? Or, somewhere out there, is there a charming Jewish doctor on a white horse waiting to rescue you? Grace Adler had many loves. Some were delightful, others were downright awful, and all deserve to be ranked from worst to best.

  1. Tom

    Tom Cassidy (Eric Stoltz), an old college friend of Grace's, asked her to decorate the hotel he had just bought with his wife. He earned a few points for being successful and owning a hotel, for giving Grace the job opportunity of a lifetime, and for being a fellow redhead. But he lost them all when he kissed her even though he was married. Pig.

  2. Nicholas

    Only slightly better than Tom was Nicholas (Jeremy Piven), another returning ex. He invited Grace out for a drink to ask her to join a threesome with his current girlfriend. Grace wanted to be adventurous, so she showed up for the fun, but backed out last minute because she's a good Jewish girl from Schenectady.

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    NBC Universal

    Though it made for one of the best scenes of the early seasons, this guy clearly was not Grace's forever match.

  3. Danny

    Danny (Tom Verica) was one of Grace's longest relationships: she broke off their engagement in the pilot episode, only to be reunited with him for one short week at the end of the first season. But as usual, meddlesome Will was right, and Danny was still a total toolbag. Grace may not win any awards for maturity, but she deserved better than this guy.

  4. Josh

    Hollywood would have us believe that the ideal partner is one who is completely in tune with our needs. Prince Charming is doting and passionate, a "yes" man whose love for the princess outshines any other joys or desires in his life. The affection cup runneth over in truly perfect relationships, and that's a good thing, right? Not so much. When Grace dated Josh (Corey Parker) -- a soft-spoken, New Age-y, forehead-kissing, walking compliment of a man -- she learned that such affection can, in fact, be smothering. But nice guys are hard to let down, and Grace struggled to break up with him. She was finally able to do so when she found out that Jack had sex with Josh. I'm sure Josh was just being nice.

  5. Nick

    Not to be confused with Threesome Nicholas, Nick (Edward Burns) was the first person Grace dated after her marriage fell apart. He was a greeting card writer and budding screenwriter who asked her to read his newest script and pass it along to Jack, who was working as an executive at a gay television network. Poor Nick deserves a spot on the middle of the list because he fell victim to Grace's growing self-centeredness; she couldn't bear to read the script for fear that it would be bad and she wouldn't want to date him anymore. Never mind his needs and dreams: this was all about Grace and her quest for love.

  6. Mark

    Mark (Ken Marino) was also caught up in the web of selfish Grace. Though Will & Grace was full to the brim with insult humor throughout its eight seasons, this may have been Grace's worst moment. Mark was a nice enough guy, but Grace broke up with him because he had six toes. Who does that? Whereas the dilemma with Nick could (in theory) have caused real problems -- how do you love and support someone if you think their life's work is crap? -- Grace's logic in breaking up with Mark was pure shallowness. She knew that, but that doesn't make it okay. Long live six-toed Mark.

  7. Ben

    Ben Doucette (Gregory Hines) was a client of Grace's who refused to pay her because he didn't like her work. When she hired Will to sue him, he offered Will a job at his swanky law firm, and eventually paid Grace what she was due.

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    NBC Universal

    Grace held a grudge against Ben for half of the second season, until she learned that the wealthy, entitled lawyer had a kind, vulnerable side. They maintained a casual, open relationship until they both realized that it was going nowhere. Ben was great for Grace because he challenged her, matched her intelligence and wit, and playfully indulged her neuroses without baiting her. Plus, he was a decent dancer. Had he not been such a playboy, they would have been a great match!

  8. Leo

    Some may be surprised to find Leo (Harry Connick Jr.) somewhere other than the #1 spot, considering he was the one who snagged the lovely Grace Adler in the end. But charm and Jewishness aside, Leo was not great for Grace. Sure, he was a smart, sweet, down-to-earth guy who volunteered for Doctors Without Borders. But he was also sneaky.

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    NBC Universal

    He lied about his real name. He had an affair. They got divorced. They hooked up on an airplane a year later, and Grace got pregnant. When she visited him to tell him about the pregnancy, she learned that he was engaged to another woman. Assuming this was less than nine months after their mile high meeting, it's safe to assume Leo was dating that woman when he had sex with Grace on the plane. Is that the kind of guy Grace should have ended up with? No! Prince Leo may be hot and suave, but deep down he's just another slithery Mr. Big.

  9. Nathan

    Nathan (Woody Harrelson), on the other hand, was Grace's Aidan -- the rugged diamond in the rough who got away. He was a sarcastic, combative slob with odd habits and simple tastes, but he loved Grace -- really, truly loved her.

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    NBC Universal

    When Karen got him a motorcycle for his birthday, overshadowing Grace's thoughtful gift of a signed, first-edition copy of Zen And The Art Of Motorcycle Maintenance, she admitted that all she had to compete with Karen's gift was her love. His happy dance in response to her declaration of love was sweet and romantic. Forget suave. Forget forehead kisses. Forget Prince Charming. Isn't life more rewarding with a partner who makes you laugh? Who surprises you with a trampoline and a note that reads "I would have sent flowers, but they're not as much fun to jump up and down on"? Face it: Nathan was the greatest for Grace, the yang to her yin, the goofball to her high-strung loon. If only she had been mature enough when he proposed to recognize that love doesn't always have to be a fairy tale, she could have saved herself a lot of heartache.

  10. Will

    Ultimately, Grace's true soulmate is not a lover at all. It's Will.

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    GifSoup

    You saw this coming. No explanation necessary.

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