Alyssa and Connor

Alyssa Di and Connor's Engagement in Spring House Hotel, Block Island, RI

How We Met

We live in a world where a tall, dark and handsome young man once locked eyes with a bright, beautiful blonde woman across a crowded stadium at a Whaler’s game. 30 years later they’re still married with two kids. That’s how Connor’s parents met, but it’s not how we met! We owe it all to a dating app that has endured a very turbulent reputation over the past six years: Tinder.

Here’s the thing, I was very picky on Tinder. I tried it in the past with zero luck, so any time I received a message that was anything less than mature and serious, I was uninterested. That was about to change, however, as my mind and perspective were vastly opened after reading the book “Love in 90 Days” by Diana Kirschner. Actually, I’m not sure I even finished the book because I met Connor before I had the chance! Now, before you jump to conclusions about the depths of my desperation (I would be thinking the same thing), I should let you in on the fact that I value spirituality very highly and had recently been on a self-development journey to learn more about myself, healthy relationships, intuition, and manifestation. So, when a friend gave me this book I figured why not?

The inspiration I took from Kirschner was to be open to opportunities. Her idea was that success is found in abundance; so why not date three people at the same time?

I thought Connor was super cute. His photos drew me in – he had a great smile and apparently a love for the outdoors and being active. I was excited to see that he had messaged me, when, whomp-whomp, he said: “that smile tho” with a heart-eyes emoji. He couldn’t have said, “Hi, my name is Connor. I think you have a beautiful smile”?? Well, the old-fashioned me would have sighed in defeat, but I only had one date lined up at the time – not my desirable three!

First impressions continue to amaze me, as when I arrived at Burton’s Grill in South Windsor, CT, a pleasant, and life-changing surprise was ahead of me. I was there first, faced with the decision of waiting an ungodly amount of time for a table to open up or to snag one of the last few open seats at the bar. Oddly, Connor didn’t make reservations at our chosen location but instead made “back-up” reservations at another restaurant down the street. I’m still confused by his thought process on that.

Some time passed while I deliberated whether or not to order a drink without him. The bar area became crowded, with people standing all around me and Connor’s seat the only one left open. Why was he late do you ask? Well, perhaps that’s a comic story that I should let him tell, but let’s just say that it involved him having to turn around in his commute, shower again, and change his pants.

Anyways, when he did arrive – it’s wasn’t that late, I just like to exaggerate it for effect – divine timing stepped in, as I turned around to search the crowd for his arrival, and there he was. His eyes met mine and he asked an old man standing between us to let him by, gesturing towards me and saying “I think that’s my seat.”

We never ordered drinks after all, which meant I increasingly became nervous, rambling on about myself and asking him questions about himself that often took him off-guard (or so he says). We talked about our lives growing up, going to school, our careers, our families, and our interests. We found that we both went to small high schools, were family-oriented and interested in spirituality and self-development. When I noticed that he had barely touched his short rib dinner, I was slightly appalled realizing that I was about to polish off my risotto – out of courtesy to the guy’s manhood are you supposed to refrain from out-eating him on the first date?!

By the end of the evening, Connor invited me over to his house. If I’m honest, I could tell that I liked him a lot but it wasn’t the promising ending I had hoped for. I’m all about modesty, respect, and for God’s sakes meeting a damn gentleman! Of course, Connor has since assured me that he only had “pure and kind” intentions with his offer (haha!)… Anyways, I said no, citing “maybe another time” – I barely knew him – and he walked me to my car.

Later that evening, he texted me to say that he had a nice time, liked that I was “down to earth,” and would like to plan to see me again.

After our second date, I was smitten!

How He Asked

I turned 27 about three weeks before Connor proposed to me on Block Island. On the morning of my birthday, Connor very excitedly handed me one wrapped package after another. He got me a book I’d been looking forward to reading, a Harry Potter edition Clue board, and a gift card to get a manicure and a pedicure.

In passing, I had mentioned to Connor that if he ever planned to pop the question, I would appreciate it if he could at least make sure my fingernails looked presentable before the whole world started looking at my hand so closely! So, when he said that I could use this gift card before we went on our upcoming day trip to Block Island, I instantly became suspicious!

Sure, I had spent some time expressing that I would like Connor to plan a date for us at some point, but when he bought the ferry tickets, reserved the moped, and booked a dinner reservation (at a surprise location nonetheless), it was a little above and beyond! He fretted over the weather, designed an itinerary for the day, and spent 30 minutes deciding which belt and shoe combo to wear to dinner.

In short, I suspected he had something planned!

It was such a fun day. I clung to his waist as we sped past the beaches and greenery of the island. We stopped at the north and south lighthouses, the Mohegan Cliffs, the beach, the Nature Preserve, the ice cream shop… As the day went on, the weather got more and more cloudy and windy. I was wearing jeans and two jackets on September 8th! It started to rain for at least an hour before we had to change our clothes for dinner, so Connor took me to the Spring House Hotel ahead of time to escape the elements while we waited.

The entire wait was mostly silent. Maybe I was paying too close attention, but Connor seemed to be feeling quite nervous! I told him I would take my time getting ready (in all honesty, I needed it as the weather had quite had the field day on my hair and makeup) so by the time I walked out of the bathroom, he was waiting for me! He stood up from the lobby bench, wearing a blue button-up shirt and khaki pants. He was holding his sweatshirt, which obviously didn’t go with his outfit, awfully close by his waist.

“I found the perfect spot on the porch to take some pictures!” he said.

Connor had gotten me a Canon digital camera for my birthday the year before. Along with my polaroid camera, I love using it to capture treasured moments and getting creative with them (hence why I have this video – I filmed the whole day EXCEPT the most vital moment!!! Luckily Connor hired Jessica to take photos!).

Anyways, it was raining and I didn’t want to go outside to take photos! But he was already halfway out the front door, so I followed with both cameras in hand. Though there was a wedding going on the hotel and the lawn was dotted with guests earlier in the day, it was now deserted except for three stragglers lingering at the end of the bar in the corner. We headed in their direction, as Connor was explaining that there was a great view of the ocean from that part of the porch.

When we reached the corner, I whispered to Connor to ask those lingering people to take a photo, quick, because it was freezing! I tried to hand off my cameras to him but he didn’t budge. In fact, was he starting to just rub my back?

“Are you going to ask them?” I said, my patience thining and desire for the warm indoors growing.

“Let’s just put the cameras down for a minute,” he said, guiding me to a nearby chair to deposit them.

“Okay…” I said, hesitant and now suspicious again.

He brought me back to our corner, facing me outwards towards the ocean, and stood against my left side with his arm around me. The next words he said, well, I’m not really sure of anymore, but I’ll recount them as best I can!

“How do you feel about spending forever with me?” he asked.

I didn’t know how to respond because part of me was waiting for more to be said, but he was beaming at me, so I probed him further: “What?”

Connor dropped to one knee and I brought my hands to my face. Probably the worst instinctual reaction ever, as I pretty much missed most of the proposal thanks to me covering my own eyes. When I collected myself enough to look at him again, he asked, “Will you marry me?” His face looked like he was about to burst with excitement, nerves, adrenaline, and – I hope (haha!) – love! I said yes, nodded rapidly, and my hands went back up to my face as I let out a few cries of emotion. Next thing I knew, the ring was being wedged onto my finger. Two things about that: one, I never even saw the ring in the box and two, I say “wedged” because it was too small and I had to jam it over my knuckle.

Connor rose to his feet, hugged and kissed me and I became aware of a clicking noise coming from the photographer lingering to our left. A couple standing by was clapping and handed me a mini bottle of champagne with two plastic cups. At that moment, the proposal was over and I looked around me, shivering from the cold, almost wondering what do to/what might happen next. The photographer asked me to show off my new bling – wait, what?! Is this ring real!? Oh my god. There’s a big old ring on my finger. I’m engaged!! I’m engaged?!

Wedding Proposal Ideas in Spring House Hotel, Block Island, RI

So many thoughts and emotions consumed me, mostly centering around realizing what had just happened. Connor started to tell me about his plans to make this moment special as we popped the mini champagne and toasted for the camera. As it turns out, the photographer had recruited the couple to wait with her on the porch so she would look less conspicuous out there by herself – they were the people I noticed lingering there earlier.

We went inside to get a few more photos, call our parents and grandparents, and gush over our excitement before being seated for dinner, where we proceeded to talk about Connor’s plans leading up to that moment (he had the ring taped inside his underwear all day!), our pending wedding and our future! My parents already knew as Connor shared with them after dinner one night (I had already left to attend a meditation class) what he was planning.

Stay tuned, a wedding is planned for August 3, 2019!

Our Video

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Special Thanks

Beeden Design (Jessica)
Photographer