I figured making the thumbnail photo of this post me getting engaged would get a ton of clicks, so here we are leveraging my relationship for internet viewership. Probably the main reason why I got on the knee, clicks.

Jokes aside, I did get engaged this past weekend to my dream girl and it was the second-best day of my life.

I mean, I was at Super Bowl 49 in 2015 with Dad for the Patriots vs Seahawks 20 rows up in the endzone that Malcolm Butler made the game-winning interception on the goal line.

Does not get much better than that.

But my engagement was a very close second. It was one of the most anticipated events of my life and it lived up to the hype.

I will say, I put a lot of work into the planning process because I really wanted to surprise her. Because she challenged me that I would not be able to do so. But I did, and here’s how…

But before I talk about planning the proposal and how I got there, I need to address my cheesy corporate takeaway since this is a LinkedIn post after all.

If you truly love something, GIVE IT YOUR ALL.

Put in the time. Put in the investment. You will be very pleased with the outcome. Even if the final product isn’t exactly what you imagined, you can be satisfied with the effort you gave.

That’s exactly, what I did here. Gave the effort.

I loved the planning of the event because I loved the person it was for. There was passion tied to it.

So, I’ll throw it back to….

August 13, 2022. I met Johanna at my favorite bar on Earth. Cisco Brewery on Nantucket. No place like it.

Now let’s fast forward 4 years to 2026 NFL Playoffs when Drake Maye was making a deep playoff run with my Patriots and it made me super emotional and want to experience the peak of “love”.

January 17. Surprise jeweler appointment in Boston. She asked in the Uber if we were doing “any shopping for her that day” since I said we were hitting all my stores. Little did she know. We celebrated the first look at rings at our favorite steakhouse, then somehow ended up in full football pads at Dick's Sporting Goods. Naturally.

Jump to May 1. Met a jeweler on Charles St alone while she was out. Fell for two diamond options, almost signed right there, but wanted to see more.

May 12. Met a different jeweler in New York right before a work meeting. This legend, Avi, helped my three brothers-in-laws buy rings for my sisters and it felt like family. Fell in love with it, paid the deposit on the spot. We were doing this.

June 3. Her sister Willa posted a photo of a small private beach in Orleans. I knew instantly that was the spot. I DM'd Willa about it that same day. She agreed.

June 5. I spent the day calling about 65 restaurants on the Cape trying to book a private surprise party. Every single one was booked for a Saturday in August. Pivoted to her grandmother's house instead.

June 7. I snuck over to meet Willa and her mom before a birthday dinner, under the cover of a "quick stop." We aligned on August 1st as the date to plan around.

June 10. Picked up the ring in New York. Had Willa meet me there that morning, which was a cute moment. Played golf at Winged Foot the same day (3rd best day of my life). Then the ring flew over to Nantucket.

June 17. Drove to my sister's Boston apartment to stash the ring in her safe while Johanna was at a Red Sox game. She checked my location and asked if I was seeing my baby niece. Told her I was dropping off picture frames from our grandmother. Clean escape, ring secured.

June 23. Secret dinner with her mom to ask for her blessing. Two-hour interrogation, passed with flying colors. Had her mom turn off her location and used a bar photo with my brother in-law as the decoy.

Early July. Locked the full plan: My family would be hiding on our boat in Provincetown, a sprinter van to shuttle everyone over, my mom "in Europe" but actually taking the ferry over from Nantucket, her mom and sister camping out nearby, a fake 6pm dinner reservation with a friend to get her dressed and in the car at the right time, a picnic company and photographer booked for the beach, and a raw bar and cake lined up at the house for after the beach.

Ok, well, all sounds good, right? Time to go execute.

Pressure is on.

July 23. Dry run. Drove to the site alone at 7:30am, filmed the layout for the photographer, practiced getting on the knee.

Practice makes perfect. We are almost in the clear.

July 25 to 26. She suggested the Cape trip “herself”, unprompted, which meant the plan was working. Spent a chunk of Sunday in traffic finalizing the fake dinner details on the phone.

July 27. Picked the ring back up from my sister's house after dropping off random things like a Mahjong set.

July 28. Briefed her grandmother on the phone.

July 31. Drove down to the Cape for the night.

August 1. Spent 4 hours on the beach reading a fantasy football magazine getting in the right mindset for the proposal (there’s a ton of value for QBs late in the 11th round this year).

Around 5:02pm. I was in victory formation.

At 5:03 I had a fiancée.

At 5:16 We were spraying bottles of champagne all over the beach.

It’s now 5:52 and our family surprised the heck out of her at her grandmother’s house.

It’s past midnight and we’re destroying a dance floor in PTown.

August 2. I had the time of my life celebrating and pumped with my execution. I was Tom Brady in the 4th quarter navigating a crowded pocket for 6 months and it paid off.

I had a future bride on my hands.

Although pretty sure I am going to be the bridezilla when it comes to wedding planning. I had too much fun with this.

GIVE IT YOUR ALL FOLKS!!! Don’t half-ass it if you love it.

See you next week. I am going to start writing these more again.

BTW click my ads for gas money.

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