HOW WE MET
So, both Christine and I were dating both socially and online, specifically on OkCupid. On a Thursday evening in late February 2014, I was briefly checking my account and noticed that she had visited my profile. I was attending an event the next day so I invited her to join me. I never did actually look at her profile. She agreed to attend and sent her number. We sent a total of two messages to each other before meeting the next day. The first date started pretty tame at a Meetup and dinner at Heavy Seas Alehouse and then evolved (devolved?) into karaoke and drag queens at The Hippo, a (now closed) local gay bar. I asked her on a second date that evening for the next day and have been together since.
By October of 2015, I knew I wanted to ask Christine to marry me, just had to work out some logistics. We were going to Hawaii for our anniversary in February so I thought that was the perfect time. My grandmother had a small diamond that has been in our family since mid-1700's so I knew I needed to act fast to ask her parents so I would have time to get the ring made.
In November, under the actual guise of taking a proctored exam, I went to her parent's house and asked for their permission. They had a few questions and then happily offered their blessing. I wanted to get Christine's best friend (and now, as she likes to call her, "Best Woman") to help pick the ring and eventually settled on a style that would require me to find a matching diamond to our family diamond. I had the ring ordered in December and picked it up in January. Meanwhile, I had to rope in the resort and restaurant staff in Hawaii to make sure our anniversary dinner went as planned.
There were a few rocky moments in January and February because Christine watches The Bachelor AND it was engagement season. I accidentally went a little far trying to cover up the proposal saying "You don't have to worry about getting one of those (ring) this season!" Christine had a long day, and this statement resulted in tears. I was able to smooth it over and calm her down--though I was reminded how much I hate The Bachelor.
MARRY ME, CHRISTINE?
HOW HE ASKED?
The vacation went splendidly and on the 4th night, on our 2 year anniversary, we went to dinner as planned. I had a custom Harry Potter Sorting Hat ring box made so I had to put in a little gift bag and carry it so she wouldn't get suspicious. I was extremely nervous and tried hard not to act out of character. The weather was a little cloudy and rainy, the way it gets in Hawaii, so it was hard to see the sunset. The resort photographer I had arranged to be there was taking photos of other guests. Once we ordered our food, and right at the predicted sunset time, I suggest that we get some pictures taken as well.
I had managed to get the ring box in my hand, and was able to propose while the photographer was taking pictures. Christine started crying so hard that she didn't answer immediately, which was a little nerve-wracking. She eventually said "Yes!" making the staff and some other guests cry right along with her. Feeling the weight lift off my shoulders, I was starving while Christine, experiencing a lot of shock, congratulations from guests, and the realization that because of the time zone differences, she couldn't call anyone couldn't eat a bite! Once I finished eating, we wrapped up her food and went back to the resort where she was able to relax by watching the episode of The Walking Dead we had missed and then immediately buying our wedding domain name, because... priorities.