Background: Im 22 years old and single. I've had a girlfriend a few years back but since then ive failed numerous times with different women. Im going to law school in a few weeks and ive committed to the 100set open challenge so I thought sharing this with you guys is a good start.

I was recently on vacation with my family, and the whole thing happened on the plane back home:

It was 8am and my family and I were boarding a plane back home from a wonderful vacation. I was supposed to sit next to my younger brother who is barely 10 on the plane but my mother decided to switch seats with me so she could sit and watch over him.

It wasnt the first time I had a complete stranger sit next to me on a plane but all previous experiences were bitter so I was not looking forward to it.

I get to my seat and store my luggage overhead. I look down and I see a very beautiful girl with hazel hair occupying the seat next to me. She looks at me and i give her a smile and she smiles back. I sit next to her, and got settled in which is just me trying to calm down before I open.

-Im sorry if the next paragraph is hard to read but I have a hard time trying to write down conversation without using plenty of quotation marks-

I said hi and I asked her what she was doing during her stay. She was visiting family and was heading back for work the same day. "How about you? what were you doing?" I replied that I was on vacation with my family and that there are some really beautiful snorkeling spots here. We introduced ourselves and started talking about work, our families, and etc. She told me she was 29 and i said "really? your 29? I thought you were 23 or something because you look amazing" She laughed and tried to guess my age but i guess my beard made me look older because she thought i was older. We continued talking about different topics and I even got some kino going on because I cheered her up when she was dreading going back to work on the same day.

We enjoyed each other's company but sadly I didnt get to ask her for her number so i could ask her out because i really dont know why. Maybe I was afraid? Was it the age difference? Looking back, i shouldve asked for her number and i shouldve complimented her eyes because she was great and had beautiful hazel eyes which i really liked.

The plane touched down. She looked at me before turning away to stand and grab her things. I impatiently wait for my family to start disembarking but they said to just wait and be the last ones off. She looks at me again, smiles and says "goodbye OP, it was nice meeting you"

Any advice guys on where I went wrong and how to improve on the whole conversation thing because I realized after i ask the common things, you can run out of things to talk about with girls. Luckily, she was picking up the slack this time, but what about with other women? Should i just take disinterest as a personal failure to be more interesting or as her just not being interested?

Its 1am and im going to bed. :p thanks for taking your time to read this post.