SecondTimesTheCharm

In my own case, after just 4 months of dating, I surprised my DW by driving her to my "favorite bakery" (at least that is where I said we were going). Instead, where I really took her was to a jewelery mart (with multiple vendors) and, together, we designed what was her perfect engagement ring.

A couple days later, without her knowing the ring was yet ready, I picked it up and dropped in on her at her office (where I had been just once before) and on bended knee in front of her boss and co-workers, I proposed to her.

It was pretty soon to get engaged but I felt pretty sure about her and, plus, I was going to be going on a 4 week international trip with her the following month and had a little bit of a guilty conscience. I had already met her parents a few times and didn't think it was right to go on such a trip without being engaged, although she was a 30 year old independent woman who lived on her own since she was 21 years old and had previously been in other serious relationships. Just old fashioned thinking on my part, perhaps, but I loved her and wanted to do the right thing in my own mind even if nobody else was demanding any such thing from me.

It was a 7 month long engagement, just enough to get everything done, and a beautiful wedding with about 250 guests, and just a one week honeymoon that paled in comparison to that post-engagement 4 week trip we took, but it was a fun honeymoon in a tropical locale.

Looking back, while it would have been nice to totally surprise her and propose out of nowhere while on some romantic getaway or in some really unique place, she has always been thankful that I included her in picking out the ring. Obviously, she couldn't have been a part of that if I proposed to her any other way. She had been engaged once before and hated the ring (although never mentioned it).