You know Skylar Astin? Of Glee and Pitch Perfect and Spring Awakening, etc., etc., fame? Me too. Only I knew him as Skylar Lipstein and he finger-banged me on my extra-long, twin-size bed while watching Say Anything... in my freshman year dorm room at NYU. I’m 80% sure I was wearing Hard Tail leggings.
The first night we made out, I knew we were going to date. He's Jewish and sort of dorky. I'm Jewish and sort of dorky. We didn’t go out to dinner. He didn't take me to red carpet events. This was before good ‘ol Lipstein traded in for Astin, and I think the most expensive meal we had was at Chick-fil-A at a neighboring dorm.
He was an exceptional kisser. The kind of kisser that makes you question how good of a kisser you are. The kind that makes you think, “Did I really say GUY X was the best kiss I’ve ever had?”
I knew Skylar was at Tisch and I consciously tried to avoid learning much more about what he was doing there. “Male actor” didn’t scream sexy to me. Until it did. And when it did, it really, really did. Yes, he sang to me sometimes, and yes, I liked it despite my best efforts not to. I mean, dude can sing.
Our love affair was fast and furious, but we remained close friends, and when he started talking about some little show called Spring Awakening, I knew that fame was going to happen for him pretty quickly.
I’d meet him between Broadway rehearsals and ask him if he realized what was happening. He’d laugh, but I knew he knew.
I’d meet him outside the stage door and see teenage girls screaming for him—MY Skylar—asking for his autograph. He’d pull me into pictures sometimes and I’d pretend to think it was totally lame.
The last year of Spring Awakening, I went to his birthday and sat next to his mother. “Can you believe all this?” I asked her. She looked at me and said,“Absolutely.” I could, too.
Skylar called me one night to tell me he was moving to L.A. I didn’t tell him at the time, but I thought it was a huge mistake. He was a singer. He needed to be in New York. What was Hollywood going to do with a musical theater dork? He’s Sondheim, not Spielberg.
Then came Hamlet 2, and then came Pitch Perfect, and then I knew it was a done deal.
When Pitch Perfect came out, I felt like I watched my entire freshman year play out on the silver screen. Okay, I wasn’t in an a cappella group and we didn’t have a riff-off (although I would have been down for that), but he does chase a girl during her freshman year of college. They do have a fast and furious affair. And I had to watch him kiss someone in (I swear) the same way he kissed me.
I texted him as the credits ran to tell him how proud I was. I also told him how weird it was to watch him make out with Anna Kendrick in a freshman dorm room that looked shockingly similar to mine. We talked for a little after that. And then we emailed a few times. And then he started dating a beautiful (famous) woman and I never heard from him again.
Last night, I flipped to Conan and there he was. I wondered whether a stylist had dressed him. I remembered that he used to always complain about being hot, and I thought he must be sweating so badly under all those layers and under all those lights. I barely heard anything he said because all I could think about was how insane it was that I was watching someone I slept with on Conan fucking O’Brien.
At work today, I glanced over a coworker perusing a gossip site that had pictures of Skylar in Cavemen. My stomach curled a little. It curled in the same way your stomach curls when you see your ex across the street with another girl, but he doesn’t see you. Only, with five million hits to his name on Google, I get that feeling all the time.
So ONTD, How would you feel if your ex got famous?