He contacted me a couple months ago and we planned the night: he took her to dinner and then to a local music festival. He then brought her to the observatory, where I gave them a tour and showed them the Moon & Jupiter through the telescopes before leaving them alone for a while. They even saw a giant meteor, which was super cool!
I hope that she enjoyed it - I couldn't really tell when I went back in (they told me it was okay to come back in, don't worry!). She didn't look overly enthusiastic, but perhaps she either knew it was coming, or she's shy and doesn't display those emotions in front of people. I felt weird when I was saying stuff like "Ohh! She said 'yes'!! How exciting!! Congratulations!!!" and they were very calm about it!
In any case, it is so much fun being a part of someone's big night - being able to do something special for them to make it memorable just feels awesome. I have done it once before for a friend of mine (and the girl had a much more excited reaction!).
Hmm...perhaps I have found myself a new career!