Kellie and Jason

Proposal Ideas Portland, Maine

How They Asked

While in Maine on vacation Jason had an elaborate plan to take me skydiving. Unfortunately, it was canceled due to inclement weather. He quickly came up with a plan B to propose after dinner in our hotel room, however, he wanted to ask for my dad’s blessing. My dad lives in Nashville, so Jason wanted to call (my dad didn’t answer).

He left a voicemail (while I was getting ready for dinner) saying, “everything is ok but I just wanted to ask you something that cannot say in front of Kellie.” My dad finally calls Jason back, but it’s too late because I am finished getting ready. Suddenly, I get a phone call from my dad asking if everything was all right since he had listened to Jason’s voicemail.

Luckily, it didn’t register in my mind what was happening, because Jason had me convinced he would never propose on a vacation. Jason was 0-2 at this point and just decided to wing it after dinner. We arrived back to our hotel room, with a view of the city lights glistening over the harbor.

He started to talk seriously about how things may have not been going as planned on our trip, he makes his way towards me, and I lean in (him making him think it’s for a kiss)—I stop him and say, “you missed a spot shaving!” He gets flustered answer says, “screw it!” (Went to the bathroom to fix his face) came back, got down on a knee and asked me to marry him. I replied with a yes, of course, and we spent the rest of the week in Maine celebrating with his family.

Marriage Proposal Ideas in Portland, Maine