How I Almost Met Jason Segel

Saturday morning as planned, I got up and made my way to my haircut appointment. My friend and hairdresser informed me that Jason Segel (How I Met Your Mother, Forgetting Sarah Marshall, Knocked Up, Freaks and Geeks, etc. etc.) was going to be in Chicago that night, doing a comedy show at Second City. She loves the guy, so of course she wanted to go. And I’m a fan of both him and trying to meet celebrities in general, so I was all about it as long as I could work it out with the hubs.

Turns out, the hubs was craving a “me day” for himself to get some work done on the basement, so Bridget duty was enough to convince him to let me run off to Chicago for the night.

I met my friends on the road a little before 8, and we drove the rest of the way to Chicago together. Earlier in the day, we had learned that Jason would be at an awards show in the evening, then doing a free improv set at 1 AM. Seats were not guaranteed for the comedy show since the paying customers for the sold out 11:00 show got first dibs. Our only option was to stand in line and hope for the best. We headed to Second City first to see if there was a line started yet. Since there wasn’t, we went on to Water Tower Place, where the award show was taking place.

After about an hour of no sightings there, we drove back to Second City. By that time, the line was at least 50 people long. Craaaaaaaaaaaaaap!!!!!

We waited for a couple hours while the 11:00 show was going on, all the while trying to keep ourselves amused and warm. I found it particularly funny when my friend would sing the “Let’s Go to the Mall” song from HIMYM, including the Canadian accent. At a little before 1:00, I noticed a really nice car pull up and some girls started rushing toward it. I commanded my friends to hurry to the car and try to get a glimpse while I held our spot in line. Jason actually rolled down his window, and a couple of girls got pictures and talked to him for a second.

One of the girls’ pictures, which she texted to a few people in line

My two friends got to the car in time to see the back of his head as the car turned the corner to go around the building. Our excitement was heightened, and we hoped even more that we could get inside to see the show.

Another half hour to an hour passed as the 11:00 show got out late, and we noticed only a dozen or so people file out. Definitely not promising. They were only able to let about 20 people from our line in, so we were out of luck. Since we couldn’t feel our toes, we went back to the car to warm up and wait for the improv set to be done. We had one more chance to see Jason when he left the venue.

A little after 2:00, we drove our car around the venue to see if we could see anything promising. We noticed the car Jason came in was parked at the side entrance! A bunch of girls (and a few guys) were already waiting in the lobby, and we were very thankful to have a warm place to stand this time. After the improv set let out, though, security made us wait outside. The three of us got a spot right next to the car, and the crowd formed a walkway from the door to the car. The driver came out and moved the car. We all started running (seriously...I haven’t run after a car in years...kind felt like a lunatic) back to the front of the building, and we secured a spot by the car door once again.

It was another hour and a half before anything else happened. The staff was all telling us that Jason had left and that the driver was inside drinking whiskey. ‘Cause that’s really safe to do right before you drive. It was just not all adding up although we were starting to give up hope. We gave ourselves a cutoff time of 4 AM. (Yes, we’re crazy. We know this.) By that time, the crowd had thinned out, and there were probably less than 20 fans there. All of our eyes were fixed on the front entrance, but my friend awesomely noticed a group of people, which turned out to be Jason Segel and his entourage, coming out a nondescript side door and darting toward the car.

It was all very quick but also very exciting and eye-opening. Although we did not get into the show like we had originally planned, it was good we at least got a glimpse.

I didn’t end up getting home and in bed until 6:30 AM. I know I won’t be able to do these crazy, spontaneous things for much longer as Bridget gets older, but I’m glad my husband doesn’t mind that I do them every once in awhile, even though he thinks I’m insane. I really wish I lived in Chicago, though. It’d be so much easier!