24 year old male here.

Growing up I was a very shy, obese kid, with low self esteem. In the last two years I've done a lot to change that. Had a lot of realizations about life when I started watching the same RP YouTubers we all watch. I'm very well groomed, great shape, and I'm about to finish my Masters in Finance (already have a fantastic job lined up!)

In the past year I've had several girls show a lot of interest in me but I was very insecure about the fact that I was 23 and never dated or kissed a girl and I didn't really give them a chance. Recently, I met a girl in passing in the graduate school lounge. She somehow found me on Instagram and added me.

One thing led to another, we went on a date together where we had dinner and explored downtown and I had a lot of fun. Ended up having my first kiss with her that night.

She asked me to go to her place to have dinner and drinks on Friday, and judging by the situation I think it's obvious there's a chance sex could be a part of the picture. If one thing leads to another, should I tell her this is my first time? Should I just try to be confident about it and play it off? How would you approach this.