Let's go to Chicago

Logically, anyone who hears the statement "let's go to Chicago" thinks of the following things in this order:
1) Decide a date
2) Book a flight
3) Book a hotel
4) Wait until the day arrives!

But when my boyfriend Jimmy and I say that....it just turns into a debacle. Let me share.

Friday around 11AM I sent Jimmy a text message saying that we should plan a trip to Chicago so I can use my Southwest airlines free flight I earned before it expires and use some hotel points I have for a fun/semi-free trip to a fun city. He agrees and says that the weekend of May 15-17 works for him. So I start looking at flights and tell him when to book a flight via text saying "7PM Friday depart from KC and 8PM Sunday from Chicago". Through multiple text messages following that, I'm half paying attention to what he's saying and half focusing on work. Apparently he actually booked the flight. I actually hadn't even taken the time to look to see if I could use my free voucher at those times--oops.

So the evening comes and we have something at church at 6:30- he comes and picks me up and says "I can't believe I just booked a flight to Chicago today, so weird". And me- not realizing or remembering he actually booked it say "Oh, you actually booked it?". Yeah, if you can guess...that is where he kind of got angry. So I call my mom while we're driving to church to try to book it for me because JC is freaking out that it will all be booked. So he pulls up his confirmation itinerary on the phone.....and we realize he booked a flight for 8AM Sunday morning. So essentially we'd be in Chicago for about 36 hours if we did that. That was when we looked at each other and said, "Yes, we are both complete idiots".

We arrive at church and get on the computers there trying to book it before our class starts, that doesn't work because I realize that I can't use my reward for the time we wanted to come home that Sunday. Jimmy gets a little irritated and I'm just laughing really hard because we have to give up for now and sit through class. I seriously laugh probably once every 15 min during the 3 hour time we were in class thinking about it. He gives me a bad glare every time I laugh.

By the time we got home I was so tired I just passed out in bed and forgot about our problem: Jimmy currently had a flight to Chicago (wrong times) but I didn't. I wake up the next morning in time to just throw some clothes on a book the flight. So in between me trying to get ready and book a flight and find a time that I can use my reward (blackout's are stupid), Jimmy trying to get ready and change his flights......at 8AM I think I have booked a flight for myself the same as his and am scurrying to get ready because we have to be back at church at 8:30. So right as I'm getting ready to step away from the computer and get ready as fast as I can, I double check one more time to make sure we have the same flights. And guess what? We don't. Mine is at 6:40 on Sunday night and his is at 6:05 on Sunday night. I yell "Are you freaking kidding me??! JC you have to fix this. I have to get ready." He goes to the computer to try to see what happened. Turns out I booked my "return" flight from Chicago actually from KC. I'm really smart, if you can't tell. No wonder I am so good at finance, my attention to detail is impeccable (obviously sarcasm).

As you guessed, I crack up and laugh hysterically while I'm trying to get ready because I think it's funny. Jimmy does not. Oh well. So I fix it really fast (thank god for Southwest airlines no change fee policy) and we head off to church...inevitably late.

Then right as we get in the car Jimmy goes "Did you even book the hotel?". My smile indicates that of course did not happen........how in the world did I ever travel for a career? Hopefully our actual trip there will not be as bad as the episode of planning it.