Smart, Charming, Strong
We first meet Skylar at a Harvard Bar when Will totally decimates this guy named Clark in a battle of wits. Afterward, Will goes to hang with his friends until Skylar walks right up to him and says:
SKYLAR: You're an idiot. I've been sitting over there for forty-five minutes waiting for you to come and talk to me, but I'm tired now and I have to go home, and I couldn't sit there any more waiting for you.
So the first couple of things we know about her is that she's smart, charming… and not at all shy. And that all makes her a pretty good fit for Will.
Although her personality mixes well with Will's, Skylar comes from a very different social background. While Will comes from a rough neighborhood in Boston, Skylar describes her childhood as such:
SKYLAR: Growing up in England, you know, I went to a very nice school. You know, it was kind of progressive, organic, do-it-yourself, private school. Then Harvard. And then med-school.
She literally sums up her life when she says, "You know, if you think about it, at the end, my brain's going to be worth two hundred and fifty thousand dollars."
She knows this doesn't sound to great to Will, especially after she's heard him tell Clark how stupid it is to spend hundreds of thousands on an education.
But at the same time, she doesn't apologize for her money or her privilege because she's a strong person with a good sense of self.
Good With Intensity
So for much of this movie, we see Skylar as a smart, charming, and strong woman who has no trouble dealing with Will's personal hang-ups. But she gets put to the test once Will starts pushing her away. When Will calls her a phony rich snob, for example, Skylar answers,
SKYLAR: My father died when I was thirteen and I inherited this money. Nearly every day I wake up, and I wish that I could give it back, that I would give it back in a second if it meant I could have one more day with him, but I can't and that's my life and I deal with it.
This is pretty much a perfect answer from a perfect girlfriend, but it's still not enough for Will.
Like Sean Maguire, Skylar cares enough about Will to push him when she thinks it's necessary. And like Maguire, she also does a great job of giving Will lots of love without becoming an emotional doormat. She even tells Will straight-up at one point,
SKYLAR: You're afraid of me. You're afraid that I won't love you back. And you know what? I'm afraid too. F*** it. I want to give it a shot and at least I'm honest with you.
She knows that their relationship is coming to a now or never moment, so she gives Will an ultimatum by saying, "I love you. I wanna hear you say that you don't love me. Because if you say that, then I won't call you, and I won't be in your life..." Of course, Skylar is utterly devastated by Will's answer: "I don't love you."
But like any strong person, she moves on and heads for California. We don't know if she'll take Will back the next time he shows up on her doorstep, but we can be confident that she'll make good choices.
Oh yeah… one more thing about Skylar. She's also not afraid to get down and dirty with Will's buddies. In fact, she shocks them with the sheer raunch-factor of her dirty jokes.