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Adventures in Travel #1 - First Flight


I figured while we are all kind of stuck at home, I’d tell you a few silly stories about my first travel adventures.

The first time I flew, I was in my thirties. I had never gone anywhere by myself. Jer and I agreed that I needed to find someone else traveling to the same conference, that way they could guide me through the process. Yeah, that didn’t happen. My sister gave me her frequent flier miles, with a layover in Chicago O’Hare. As I prepared, she realized the airline had forgot to book my connecting flight. There weren’t many options left. I ended up flying a red-eye flight right after the daylight savings time had happen. Jer gave me direction on what to do, how to be safe, who to tip and how much. My sister loaned me a lot of professional business wear. With way too much luggage and totally overdressed in my pencil skirt, I boarded my first airplane. I only had a thirty-minute layover in Chicago. Thankfully my sister had told me the airport was huge. Unfortunately, I didn’t understand how huge until I was running through the full halls in my heels, skirt, and dragging a ton of luggage behind me. Sweating under my business suit, I made it just in time to board the next flight. Arriving around six am, I hunted for the baggage claim. Feeling relieved, I spied my suitcases coming my way but they were heavy and I struggled to pull them off the conveyor. A big African American man dress in his airport uniform offered to help. I worried about how much money I had to tip and politely declined. He watched me struggle before moving in front of me and pulling my luggage off the conveyor belt. Exasperated he ask, “Where do you want to go?” I needed to get a bus ticket. He walked me to the counter, carrying my load and left before I could say thank you. I successfully got my ticket but now wrestled my many bags to the door. I was just trying to get the door open to cross the street, when the same kind and rather frustrated man walked over to me and picked my things up again. “Where do you want to go?” I wasn’t exactly sure, “To the bus, across the street?” He swiftly moved while I worked to keep up with him in my stupid pencil skirt and heels. After dropping off my load, he left before I could offer him a tip. By this time, I hadn’t slept all night, needed a shower, and felt emotionally exhausted. The conference was being held at a really nice hotel, iconic in the area. I had know idea, I just thought that I needed to stay in the hotel they mentioned in the conference. The busboy helped me to the room. I dropped it everything right at the entrance, blocking his way. In the end I forgot to tip him. Awkward.

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