A possible Happily Ever After Story?
I am in need of some advice - thank you ahead of time for reading this :-) Let me give you a brief description (will try to be short). When I was in my late teens/early twenties, I met this girl and immediately fell head over heals. We saw each other for a couple of years just like a normal dating couple BUT neither of us could muster the courage to take the plunge and really tell each other how we felt so the physical component went missing. I loved her so much that at that time I would rather spend time with her instead of risking rejection and not see her anymore. Time passed and we didn't speak for about 8 years, all the while dating others. I got married at 26 (divorced at 30, 33 now) and as bad as this sounds, she flashed through my mind the day of my wedding. I guess I always considered her my "Allie" (The Notebook). Her best friend also told me that I hurt her because she was so in love with me when we were so young. However, many years have passed and I fully realize things can change.
In my early to mid twenties, I became very ill and made what would now be called a bucket list. I promised myself that if I got the opportunity again and our paths crossed, I would go for it. We have recently reconnected and I took her out to a piano bar (even played for her and the rest of the people in the bar) and ended up at her place for the evening. Both of us had waaaay to much to wine and pretty much fell asleep shortly after laying down on the couch back at her place. Having to work in the morning, I quietly woke her up with a kiss on her forehead and whispered that I had to go. We've texted/talked a few times since but not made any concrete plans. Our conversations have been "light" in nature (we both like to kid each other and laugh).
Thankfully, due to time, maturity and confidence, I will not fail to express my feelings this time; however, my ideas have been somewhat limited so far. I'm thinking of taking her to one of the tallest buildings in the city, bringing a bottle of wine, going to the rooftop which has great views and talk for a while. She likes to hear me play and the building has a banquet room off of the roof (which is usually empty) with a full grand piano. I learned the song "Vanilla Twilight" with her in mind. I would dedicate and play the song for/to her and then reveal everything to her. If she doesn't reciprocate, it sure would be an uncomfortable ride back to her place though!! But I feel like no matter the outcome I will feel better about myself and can at least rest knowing I gave it my best shot.
Is this a good idea? How should I handle the ride home should she not feel the same way? I welcome any advice and please don't be shy about sharing any criticisms. Thanks again for taking the time to read and hopefully respond.
