Stephanie & Matthew: Our Story

In mid-2007, I decided to move back to the Boston area for a variety of reasons, but ironically none of which was Stephanie. (Remember, she and I had basically lost touch.) Then all of sudden, completely out of the blue, she called me one night. She actually remembered my parents' phone number which is how she tracked me down in New York. We talked for over an hour and it was as if no time had passed. We still had the connection we had back in high school. We shared stories of our previous relationships and realized our similar our situations had been. But she and I were clearly happier now, and I couldn't help but thinking - hoping - that this could lead to something really great.

We continued to talk on the phone on a more frequent basis and began hanging out on the weekends back in the Boston area. I went to see a show she was performing at in Boston, which was absolutely amazing! And she even joined my family for Thanksgiving dinner, which was unexpected but awesome at the same time!

The Saturday after Thanksgiving, she made a bold move. She said that once I move back to Boston, we should go on a date. The girl I was crazy about was now asking me out on a date! I replied, “Why wait until then?” and instead suggested we go out the following weekend. The funny thing is that she had never before actually asked someone out (lucky me!). So on December 1st, I took her to Sorellina in Boston and had an amazing first date.

New Years was coming soon, and neither of us had any plans. So Stephanie came to visit me in NYC for five nights (yes, five) over New Years. I was moving out of New York the following weekend, and I knew there were parts of NYC I certainly was going to miss. But what better way to spend New Years than with the girl you have been crazy about for over a decade? We were both a bit nervous that spending so much time together at once could send our relationship in the wrong direction, but it was definitely worth the risk. Those were six magical days and five magical nights. Sixteen years later, I had broken out of the Friends Zone!

On January 23, 2008, I moved to Boston. Now I was in the same city as my family, my two best guy friends, and my girlfriend. Stephanie and I both worked in Boston so naturally we quickly spent a lot of time going out in the city trying out new restaurants, wine tastings, college alumni events, etc. We continued to connect on so many levels just like we did back in the day. Another added bonus was that she connected extremely well with my best college friend Mark and his fiancée Kara who both live in Boston. Since then, the four of us have had numerous double dates which have been awesome.

While we had only been dating about five months, we have known each other for 15+ years, and there wasn’t a shadow of a doubt that I wanted to be with her forever. So Saturday, May 10th I planned a picnic for the two of us out on Castle Island. As an inclement weather backup plan, I cut out a sun and clouds out of posterboard and hung them in the condo for an “indoor picnic”. But luckily the weather cooperated. A bit overcast, but improving. So we went to Castle Island. After the picnic was mostly set up, I casually handed her a can of peanuts which she then opened, only to find (in place of the peanuts) a ring box, and of course the ring inside the box. Her eyes began to swell and I got on one knee and asked her to marry me. Lucky for me she said yes! The sun began to break through the clouds and we proceeded to have a wonderful picnic overlooking the water.