I am reaching a point where the ‘kids’ I photographed over the years in school are now adults and are getting married. I am so excited for Marie and Tommy; they got engaged right before Christmas. The next day, we started planning their engagement session. We held off hoping for some snow, and today was the day. These sessions are extra special when I have seen them grow up and start their next chapters. Even better when we can get nature to give us the setting we hoped for.

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I was honored to take photos of a unique proposal a few weeks back. I was asked to hold on to share for a bit so everyone could find out before the pictures went up. Matt had set up a photo session with the Southwick Zoo that, unknown to her, turned into a marriage proposal. We took some photos with the deer and fed and walked among them. Then without Allison knowing, her family and friends were brought in for the big moment. It was a perfect evening that ended with a “yes.”

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Before we go too far, Colleen said yes. I have known Patrick since he was a kid, part of a great family in town that I was lucky to get to know and become friends with through baseball. So when he wrote to me a few weeks back to ask me if I photographed proposals, I was excited and felt old at the same time. He filled me in on the plan. We were going to meet at Merrimac College, where he met his future bride while they both attended. They met in Deegan Hall, now have a six-month-old puppy – named Deegan, who would be the excuse for the photo session. A perfect day, a quiet campus. We walked around for a bit, working our way to the planned spot where he would ask the question. It all went perfectly. Our session with Deegan turned into an engagement session, and I got to hear the story of how they met while touring their campus and their recent past. Here is to a long future. Thank you for having me document this part of your story.

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28 years ago today, a good friend and I decided we might be better off dating. 25 years ago today, I gave that girlfriend a ring, proposed, and decided we would be better off as married. Today as a surprise, she has a new ring with the same stone, because I decided I was broke 25 years ago and decided it was time for an upgrade. Here’s to at least another 25 years celebrating this day of great decisions.

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These unused tickets are from a taping of the Late Show with Letterman 25 years ago today, Monday, February 19, 1996. Tonight’s guests X-File’s Star Gillian Anderson, Opera Singer Cecilia Bartoli and famous for being famous (?) Kathy Lee Gifford. I was supposed to be in the audience with my then-girlfriend, now-wife Barbara.

I am not sure she even knows parts or the whole story. I assume she reads the blog, so she might now. I found these tickets while cleaning out some old things a few weeks back. In 2021 cancel culture Letterman is not having a good week, but he was the man back then – at least to me. I was a fan since I was a teen and Late Night Days. This was the new show on CBS days. It took up to 6 months to get tickets to the show. You had to write to them – pen, paper, and stamp – for tickets. They were free, but you were given the date, and it was not changeable.

Barbara and I had been twice in previous years. We watched his show nearly every night together. At one of the shows we attended in 1995 – the one with Kevin Spacey (another thing aged badly) and Crash Test Dummies – Mmm Mmm Mmm Mmm, it occurred to me, I want to get engaged at the show. It seemed like an easy thing to do. I will just write to them and explain how it would work. How can they say no? Even back then, I kind of just did things. It would be great for his show, right? I am doing Letterman a favor really. At the very least, we could do it before the show.

I was not asking to be a guest. I mean, if he wanted to bring me on stage, I would be happy to do so, again whatever is good for the show. Having been there a couple of times, I knew how it worked. Dave comes out, talks to the crowd, casual, joking, etc. It would be a perfect time to ask her to marry me. Dave comes out, picks on me in the crowd, back and forth, banter, we play off each other, all planned – “What brings you here, young man?” “Well, Dave, thanks for asking… ” boom down on a knee and engaged! Roll credits, Dave comes to the wedding, maybe officiates? We could work around his time off. I wrote all this in the letter, very detailed, bullet points, etc. hardly any work on their part.

Now, as I said takes about 4-6 months to get the tickets. I had just started the process to try to buy a business, and I was finishing school. If I request at the end of January, that will put us in April-June. This could work out, it all could be worked around, plan a trip to NYC in the spring, and we had done it before, so it made sense would not seem suspicious. Wrote letter and mailed it. Ten days later, TEN…. I get a letter back with two tickets for February 19 – mere days away. I am not ready, and this was not the plan, the spring trip was mentioned in the letter on page two. And there is NO mention on my plan. Not even a “got it Tim”, just a form letter some intern probably typed out.

All these thoughts – the tickets are numbered, will they know it is me? How? Would we have to rehearse, but she is with me. I could send her to the M&M store. Will I get the script to learn? Why would we go in February? She is going to say it’s cold to wait in line in NYC. I got school, three jobs, she had work, it’s a Monday. I don’t have a ring yet! That was a big part, no ring. Needless to say, we did not go. I could not even tell her. It would have given away I was going to ask her to marry me. So that was it, not getting engaged at Lettermen. Hid the tickets and did not talk about it for 25 years. I watched the show that night. She sat beside me, the whole time wondering if they were looking for the couple with tickets 229 and 230. I doubt it, but we will never know. Though they just tossed me the tickets as fast as they tossed my letter and well-thought-out plan, I am sure.

We got engaged that summer. That’s a whole other story that will be celebrating the 25th anniversary in a few months too.

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