I’ve very new to pick-up. 26, just got out of a 5 year relationship a few months ago. Never been particularly good with women, but sometimes things have just fallen into my lap. I'm confident at work and well put together but I have severe approach or transition anxiety even when I get several obvious IOIs.

I have a story from yesterday that I’m not sure how to dissect and learn from. I was traveling to Michigan for work and had a layover in Wisconsin. I was hanging out in the terminal reading a business magazine. I kept on catching this cute girl glancing at me and smiling. She was on my flight and ended up having the seat next to me, although there were plenty of open seats on the plane and ended up sitting across the aisle, while I said “I don’t want you to sit next to me either” with a smirk on my face. We chatted for the 30 minute flight, and was teasing her quite a bit, including her studying to be a pilot but being a little claustrophobic and afraid of heights. We had a few good laughs and she kept on turning to me to engage me in conversation.

She was only going to be in town for that night, it was a spontaneous trip she had booked the night before and theoretically planned to meet up with a friend or two in town but had no idea what to do since she’s never been here before. She also mentioned she was planning a trip to NYC (where I live) in December and was asking for my advice. Once off the plane we were both headed to the baggage claim and rental car area. At that point I choked and just said it was great talking to her and we parted ways even though I saw her again for a second at the rental car booth. Once I left I was kicking myself (per usual) about not even asking for her number.

I headed to my hotel to check in and just as I was wrapping up, the girl comes in behind me. I casually joke about her following me and stalking me (I had mentioned I was going to stay at that hotel and she never said she was planning on staying there too). She digs it, jokingly replying “You’ve only noticed me stalking you for the last hour or two.” I move to leave then ask her for her number, suggest me do something tonight, or if not when she visits New York. I have to get to the office I’m working out of so I say bye and take off.

I give it a couple hours then text her “I’m glad you didn’t follow me to work too. ” and about 45 minutes later she responds “… or are you?!” It’s busy at the place I’m working at and it takes me a while to text back that I got some suggestions about places to check out in town, and asked if she had any plans yet. I end up grabbing a drink with some of my colleagues but don’t get any response. I give her a call at around 8 and don’t leave a message. No response. I’m not exactly sure what happened.

Thoughts? Thanks!