Secrets of the Engagement

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Hayes engagement

When my 27-year-old son Hayes called a couple of months ago to confide that he was in the market for a diamond ring, I wasn’t surprised. He and his brother Vince seem to go to a wedding every couple of weeks. Their demographic has begun the march to the altar, and Hayes and Maria have been together since junior year of college.

Nor was I shocked when he shared his budget for the purchase since it had already been explained to me that the “rule of thumb” for an engagement ring is three months of the groom’s gross salary.

These millennials have definitely done some work on the rules of thumb, I can tell you. For example, take the bachelor party. Old rule of thumb: lost night in a strip club. New rule of thumb: Four-day weekend in Colorado or New Orleans.

Or the documentation. Old rule of thumb: professional photographer. New rule of thumb: engagement shoot, shower shoot, boudoir shoot, Save-the-Date photo magnet, and on the day itself a paparazzi brigade, including hired guns and camera-savvy guests, plus optional photo booth and flying video drone. All posted on the wedding website.

My son Vince, who is a bit of cynic, has observed that his entire generation lives on the scale set by reality television and Disney princess movies. Every Jack and Jill (or should I say Chase and Caitlyn) has their own publicity machine, with Instagram feeds, Facebook posts, Snapchat stories and Twitter scandals. Once upon a time, you only had followers if you were Jesus. You took a picture of yourself if you had a photo class in college. Now a day without a selfie is a day you dropped your phone in the toilet. Weddings are envisioned along lines established by The Bachelor, The Bachelorette, Say Yes to the Dress, and Bridezillas.

Hayes has always been a bit of a stealth bomber. He seems like a quiet, buttoned-down guy, but he’ll surprise you. There was the day he quit varsity football and joined … the golf team. The day he told me he had received a nomination from Rick Santorum to the U.S. Naval Academy. The day he called me from his fancy new job in New York City and asked me, in a small voice, to please come get him.

Which is to say that despite everything I knew about millennial betrothals, and some inside knowledge I have about his party-planning ancestry, he really blew my mind with this one.

He told me he planned to pop the question on an upcoming vacation to California; I suggested he do it at home before the trip. You could plan something clever, I explained, like in one of your favorite restaurants.

What do you mean?

Oh, like have the waiter hide the ring in the dessert or something. Maybe Google “extreme proposals.”

A week later, he called again, to see if his sister Jane and I could come up to Boston on a Saturday in a couple of weeks to be part of his extreme proposal — a scavenger hunt which would involve friends and relatives from all over the country.

Damn, I can’t, I said, because I had a houseguest coming that weekend and I thought it would be rude to cancel.

And then I got sadder and sadder, especially after I was enlisted to proofread the Word file with all the adorable clues. But then the houseguest told me she might not be able to make it. Don’t even try! I said, and immediately started counting my frequent flyer points.

Maria woke up that morning and reached for her phone to see what time it was. It seemed to be stuck on the nightstand. When she turned on the light, she saw it was duct-taped down with a note attached. “Today, March 5, 2016, is going to be one of those days we think about, celebrate, and cherish for the rest of our lives… and at the end of it I’m going to ask you a life-altering question.” It directed her to get dressed and do her makeup but not her hair. This perplexed Maria, since Hayes certainly knew she would not like to be seen anywhere with hair au naturel, so she tried to sneak it in anyway. But she was interrupted by one of her best friends, Lauren, who showed up with breakfast, a stretch limo, a custom playlist and the second clue. Which led them to a salon for manicures and blowout.

There, three guys she went to high school with in New York were waiting, with another clue. And the day continued like that. Each clue took her to another sentimental location — their favorite club, the first place they kissed in Boston, the Harvard building where she was doing her orthodontics training, the law library where they studied together – and at each place, some unexpected person waiting with the next clue. Including a pair of college friends who had flown in from California.

Hayes was nowhere to be seen, of course, since he was zooming around the city, going back and forth to the airport and the train station to pick up up out-of-towners, give them their clues and drop them in their target positions.

By the time the limo pulled up in front of the dental school building where Maria’s mother, Jane and I were hiding, there were eleven people riding along.

Maria is from Ecuador; her family moved to the States when she was in sixth grade, and there are still a few English colloquialisms her mom, Maria Rosa, is not familiar with. For example, Maria Rosa told us, when Hayes told her he was planning a scavenger hunt for the engagement, she had to look it up in the dictionary. There she got the impression that Maria would be searching through the garbage for her ring.

So, as she confided to us as we lurked in the dental lobby, she was quite relieved. She also said she was sure that Maria had had no clue of what was going to happen since just the night before she’d called to say how much she missed her mom. When would they ever see each other? She talked about a (fake) spa party she’d been invited to the next day.

After the fourteen of us had a late lunch in another historic location, the limo dropped all of us back at the apartment and took Maria alone to a final site. Here it is:

Hayes and Maria engagement

This is a picturesque colonial street in Boston that Hayes found recommended on a wedding info site, and the picture was taken by a surveillance photographer hidden behind a car.

The newly engaged couple returned to join the friends and relatives gathered at the apartment, which had been stocked with champagne and decorated with a giant mobile featuring over 200 photographs of Hayes and Maria from the seven years of their relationship. (The roommate gets credit for this one.) Later, we all went to dinner at an Italian restaurant on Newbery Street. This was where I learned about the app Venmo, the millennial way of splitting a check.

In the morning I proudly cooked brunch for everyone, baby boomer style.

Hayes never met my father, who was part of a group of friends who loved to plan elaborate practical jokes and other schemes – I remember a Mission Impossible party from my childhood where invitations were issued on cassette tapes (“this is your mission if you choose to accept it…”) and a chartered bus took guests from a meeting point to a secret location. Hayes’s own dad, who died when he was six, contributed the hopeless romantic gene. Both of them were on my mind, and of course my mom, who was Hayes’s biggest fan until her death in 2008. And his little brother, Vince, the aforementioned cynic, who would ultimately be the best man but was not with us for the engagement extravaganza.

When reached by phone, he dourly pointed it out that his overachiever brother had screwed it up for everyone else. “Fuck Hayes,” he said. (I think that is how millennial bros say I love you.)

Rumor has it the wedding will be a year from September — which gives us eighteen months for nuptial pre-game, millennial style.

Have an entertaining proposal story to share? Tell us your story and win a gift certificate to Pazo! We’re giving one to Hayes and Maria, too. Send submissions to [email protected]

University of Baltimore professor Marion Winik is the author of First Comes LoveThe Glen Rock Book of the Dead, and other books. Visit to sign up for a monthly email with links to new installments of this column, other essays and book reviews.


Marion Winik
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  1. Hi had a nice holler, especially here: Every Jack and Jill (or should I say Chase and Caitlyn).” So sweet, especially the picture treat at the end:)

  2. Marion, this could be my favorite post of yours yet. I started chuckling at “Chase and Caitlyn” and I ended the read laughing harder. Thanks for this mid-week treat!

  3. Oh, this is the most wonderful story – I felt that I was with all of you ( wish I had been)!! My son Matt is a good friend of Maria’s – they met at Georgetown. Maria is a brilliant,breathtaking passionate, dazzling, gorgeous young woman. Matt has told us what an incredible person Hayes is as well. (And when I meet him, I’m sure I’ll have many glorious adjectives to describe him as well)Your family is certainly lucky and Maria is so very lucky to be blessed with such an incredible mother in law! You’re always going to have beautiful teeth!!Wishing you all love, good health, happiness and peace.

  4. This article… as well written and engaging as it is… gave me a panic attack! I am so out of touch! So “old rule of thumb!”. Thank you for sharing. I feel like you’ve (once again) opened my eyes to the world that is constantly changing. Congratulations to Hayes and Maria! We luv ya Vince!

  5. Viva Hayes and Maria! I’m staggered by this level of coordination and intricate timing! And love the baby boomer style brunch. Love to all ??

  6. Any mention of Hyman and Jane always brings back fond memories. I’ll have to ask Aud about the Mission Impossible party and will share this blog post with her. Love the whole story!


    • Great to hear from you!! Hope Aud enjoys. I was hoping some of my parents’ old friends would see this!

  7. Having read (and reread several times) all of your books, I’m now looking at the sweet picture of the 3 of you from 1998’s “The Lunchbox Chronicles”-I have tears of happiness for you all! Mazel tov!

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