Proactive TL;DR: I'll definitely be seeing her again.
My expectations and whining evaporated into thin air several minutes into it since I was caught of guard by her surprisingly bubbly and dulcet voice. She kept apologizing about being late which I found cute and told her I'm the one who's usually running late. Suffice to say, she looked much better in person as I would tell her so later on. The more she spoke, the more attractive I found her since she hit all the chords I like including being sarcastic/funny.
It seems that I tend to hit it off well with Midwest girls on the first date for some odd reason. She's a flight attendant with a bunch of hilarious travel stories. I wasn't bored and found all of it very fascinating. I initiated a little bit of touching as we walked to the park.
Suffice to say, it was one of the best dates I've been on this year. The jokes were light, she was smiling a lot and laughing at my wisecracks/blunt observations, and the best part was I didn't overthink a single thing because fuck it. As soon as we got to the park touching sporadically progressed. By the time we got to the grassy area near where a free concert was happening and sat down, sexual tension was high we touched a bit more. I saw her look down at my lips and got the signal I was looking for but it didn't happen until much later when we were sitting by a pond/fountain area since she didn't feel comfortable making out around so many people after I touched and smelled her hair.It was light and a tease but I finally stopped overthinking so damn much and went with the flow.
We held hands the most of the way back to the subway while we navigated out of the park with me occasionally me holding her umbrella with my free hand around her shoulder. I kissed her on the cheek before her stop. When we got off on her stop since I had to transfer trains, we parted with a bit of a long hug and another fleeting, light kiss then agreed it was fun. I wanted more but that will have to wait until date number 2. It was a Monday evening well spent being that I was able to be my honest myself.