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Top Five Best Promposals

Owen Steven's promposal to Deirdre DiMauro

Owen Steven's promposal to Deirdre DiMauro

Owen Steven's promposal to Deirdre DiMauro

Owen Steven's promposal to Deirdre DiMauro

Top Five Best Promposals

Find out what some of the most creative DHS promposals are this spring!

April and May are very busy months for sophomores, juniors, and seniors here at Darien High School. These two months (and maybe more if you are super eager) are filled with dress fittings, hair appointments, spray tans, shoe shopping, nail appointments, and promposals. Some girls even get their prom dresses in February and finding a date starts as early as January. I have known girls to order more than 10 dresses in hopes to find “the perfect one”. To some people, prom is the best night of their life and for others, it is simply an event “they have to go to”.

To most students at DHS promposing is a nerve-wracking activity and can cause some major anxiety for those who don’t know their dates as well as others. It can also be looked at from a very exciting perspective that the majority of students look forward to planning them. This spring DHS has had some of the best promposals yet, ranging from pouring gallons of milk to showing up to Rowayton Market via a tube. Continue reading to find out about the best five promposals so far in the weeks leading up to May 18th.

One of the funniest promposals that happened this spring was between seniors Owen Stevens and Deirdre DiMauro. Stevens was the one promposing to DiMauro at a mutual friends’ house. While DiMauro was in the backyard tanning by the pool, Stevens hid in the woods behind the pool with a deer mask on ready to pounce. Stevens and two other friends who were dressed in camouflage outfits turned up the creepy music, ran out of the woods, and jumped into the pool all while Stevens had the deer mask on. DiMauro quickly caught on to the act and knew Stevens was prompsoing. Stevens held up a sign and it read “Hey Deer (druh) I Heard You Are HUNTING For A Prom Date…I’m GAME (please don’t shoot)”. Who could say no to Stevens’ genius and punny promposal?

“It was a very funny and a very Stevens-like thing to do. His creativity never ceases to amaze me,” DiMauro said.

DHS’ next best promposal was senior Drew Evanchick’s rafting experience in Rowayton, Norwalk. Drew Evanchick promposed to senior Hannah Riegel on a tubing raft in the Long Island Sound, paddling with a kayak oar to Rowayton Market where Riegel and her friends were enjoying lunch on the outside deck. It is safe to say the Riegel was very surprised and was impressed with Evanchick’s promposal on the water.

“I give Evanchick a lot of credit for paddling out in the Long Island Sound. That was a very risky, but sweet way to prompose,” senior Shane Ford said.

Following Evanchick’s wet promposal, pouring gallons of milk on your date was another risky way to prompose. Senior Carly Rutledge was taken by her friends blindfolded to Pear Tree Point Beach where her  prospective date senior Bobby Keeney was waiting. Keeney was in front of Rutledge with a bouquet of flowers and a sign that read “We go together like Milk & Cookies… PROM?”. While Keeney was promposing, Rutledge’s friends – who drove her to the beach – stood behind Rutledge on the flatbed of a truck and poured gallons of milk on her. Students at DHS were surprised that Rutledge said yes to Keeney, thinking she didn’t like getting gallons of milk dumped on her head, but I guess Rutledge really loves milk!

“I was shocked that Rutledge said yes to Keeney! I would not have been in the best mood after getting gallons of milk poured on my body,Junior ” senior Kerry Blatney said.

This next promposal doesn’t involve any wetness, but it does involve a four-legged friend.

I was shocked that Rutledge said yes to Keeney! I would not have been in the best mood after getting gallons of milk poured on my body ”

— Kerry Blatney


Junior George Thompson surprised sophomore Caroline Phillips with an iguana and a poster saying “Caroline, I-Gunaa take you to PROM”. Phillips said yes and as an added bonus got a new pet! Many students weren’t surprised that George went to the pet shop for his promposal.

“It is typical George to show up with an exotic animal for his promposal. I don’t expect anything less,” senior Marlene Dumas said.

The last promposal that made the top five was senior Samantha Berry’s promposal to senior Chris Vernal on May 4th. Because May 4th is Star Wars Day (May the fourth be with you) Berry dressed up as a stormtrooper and surprised Vernal with a sign that read, “Why join the DARK SIDE when you can join my side at PROM? Don’t make me go SOLO…”. Personally, this was my favorite promposal because the Star Wars movies are great and May 4th is a day to celebrate.

DHS students are clever and full of jokes when it comes to promposing to their dates. Take some of this year’s best promposals for some inspiration for next year!


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