Real Weddings: Penny and George

Penny Evangelakos, a public relations account manager, and George Alafogiannis, a carpenter, met as teenagers and started dating in 2009. While they always intended to spend the rest of their lives together, they were in no rush to get married. After 14 years, they finally tied the knot in an intimate destination wedding in the rolling hills of the Sicilian countryside. Here’s how it all came together.

Penny: George and I met when we were teenagers. We both grew up in East York, and I was friends with his brother. By the time we started dating, in 2009, we’d already known each other for years. But we weren’t formally introduced until this one night when I was 18 and George was 21. I’d gone out to a club with my girlfriends, and George happened to be there with some of our mutual friends.

George: Once we were introduced, we talked for a long time. I wish I remembered what we talked about, but it was so long ago and we’d had a lot to drink. At one point, I went to step outside for a second and asked Penny to hold my drink. She looked right at me and said, “Not without a kiss.” So I kissed her.

Penny: I’ll chalk that up to liquid courage. Later that night, my friend drove a few of us home, including George. When he got out of the car, he asked me for my number. I was really flattered. I’d always found him attractive.

George: In the week or so before our first official date, we saw each other a few times at larger gatherings. Many of our first moments together were spent hanging out with friends at the park or in the parking lot of a nearby Tim Hortons.

Penny: Our first real date was very casual and sweet. We walked to Dieppe Park, where we ate ice cream on the bleachers and talked. After that, we went to Blockbuster and rented a movie. To this day, neither of us can remember what the movie was.

George: Shortly after our first date, we took a weekend trip with our best friends to Montreal. That was when we both realized that we were developing strong feelings for each other. I felt a magnetic pull toward her, and our friends teased us about how openly affectionate we were. I knew from those early days that I wanted to marry Penny, but there was never any rush. We’ve been so fortunate to be there for each other through major milestones, like graduating from high school, heading off to college, graduating from college and moving into adulthood.

Penny: We spent so much time growing together. I always knew I wanted to be with George forever, but marriage wasn’t initially a make-or-break for me. I was never a girl who fantasized about a big wedding or anything. I vividly remember, though, the moment when I realized I actually did want to get married. We were in Greece in the fall of 2019, staying at this beautiful rental home in Milos. Honestly, the whole time, I kept thinking that he was going to propose, and when he didn’t, I was bummed! I thought to myself, Oh, shit, I guess I really do want to get married.

George: The plan was always to propose to Penny in New York. We’d been there together many times, so it felt right. I finally popped the question on February 21, 2020. There’s this restaurant we love on the nicest little street in the West Village. I made dinner reservations there and proposed afterward, while we were walking home.

Penny: I think it must have been about 1 a.m. We were walking past all these beautiful brownstones, and then he got on one knee, in the middle of the street, and asked me to marry him.

George: No one else was around. It felt like New York paused just for us. I’ll never forget it. We’d been together for 10 and a half years, but that didn’t make me any less nervous. Luckily, she said yes.

George: At that point, we were both still living separately in our parents’ homes. So we started looking for a place together and signed our first lease for March 1. Just as we got our furniture in, everything shut down because of Covid. So we didn’t start planning the wedding until ten months after we got engaged. We knew for sure that we wanted to get married in Europe, and trying to plan a wedding abroad during a pandemic seemed quite stressful. But, in the end, it was nice to take things slowly.

Penny: Aside from the uncertainties inherent to planning a destination wedding during a pandemic, the process ended up being fairly chill. I knew I wanted to find a venue with beautiful architecture so that the setting could be the main “decor” element. I came across our venue on Pinterest and instantly fell in love. It’s a beautifully restored 19th-century masseria, or large farmhouse estate, in southeastern Sicily, called Dimora delle Balze. It’s nestled in between Noto and Siracusa. At first, George really wanted to find a location in Greece, since our families are both from there. We looked at a lot of stunning wedding venues, but I couldn’t get Dimora out of my head. That was the venue for me. In the end, we booked it for three nights so our immediate family and friends would be able to spend some time there.

George: One of the main reasons we chose Dimora was its picturesque location. The estate is surrounded by rolling hills, vineyards and olive groves, with breathtaking panoramic views of the Sicilian countryside. There’s also a pool and a large projector screen for movies. I won’t lie, Penny did most of the wedding planning. I live by the “happy wife, happy life” maxim, so I let her do her thing. I did want to help choose the band, though. We wanted live music that drew inspiration from southern Italy and the Mediterranean. In the end, we had a Sicilian folk band called Domo Emigrantes play through our ceremony, cocktail hour and dinner. They had an accordion, a violin, a tambourine and a guitar, and as a special treat for us, they brought a bouzouki to tie in a bit of Greek tradition. To this day, everyone tells us how great they were.

Penny: I had a clear vision for my dress: timeless and elegant but with a contemporary edge. I went with long sleeves, delicate lace and a plunging neckline for extra wow factor. I didn’t need to try on a bunch of dresses before I found the one. Andrea, from White Toronto in Yorkville, messaged me one day to say they’d gotten a Berta trunk show in and there was a dress she wanted me to see. The moment I put it on, neither of us spoke. We just knew.

George: The wedding day was one for the books. It was an intimate wedding, with just our 33 closest friends and family. The ceremony didn’t start until 4 p.m., so we all had breakfast together in the garden. I spent the rest of the morning by the pool while Penny was getting ready.

Penny: I went back and forth between getting ready and hanging out on the terrace of our suite. It was peaceful and perfect, but I was extremely nervous about the vows. I’m not openly vulnerable very often. I literally sat in the bathtub finishing them right up until I had to walk down the aisle.

George: That was honestly the most beautiful moment of my life. The band walked just in front of her, which is a Greek tradition. It was nice to have a piece of our culture tied in.

Penny: As soon as the band parted and I saw George, all my jitters immediately went away. The ceremony was easily the most meaningful part of the day. It took place under these gorgeous trees near the entrance of the venue. After that, we moved to the giardino d’inverna, a garden surrounded by ancient stone walls with a charming atmosphere. The space was lit up by single-strand lights draped across the courtyard. That’s where we had the reception, dinner and dancing.

George: The look and feel of the day was inspired by the venue and the rural Sicilian setting. We incorporated elements of the venue’s traditional stone build, lush gardens and panoramic views while also infusing modern and vintage touches.

Penny: The colour palette was inspired by the natural beauty of the countryside, with earthy clay tones and soft rose pastels. We kept accents, like our florals and tablescape, minimal. We did a mixture of clay- and rose-coloured flowers with candles that cascaded down one long table. Several of our friends gave touching toasts. It was magical to have the most important people in our lives gathered around, laughing, drinking and celebrating. After dinner, everyone was ready to party.

George: We kicked off the night with a first dance to “Beyond” by Leon Bridges. Then the DJ started playing and didn’t stop until the early hours of the morning. After the wedding, we went to the Amalfi Coast for about a week. We stayed at the Miramalfi Hotel and spent our days by the sea on the private cliffside dock. At night, we’d walk into town for dinner and drinks. We spent a lot of the time reminiscing about the wedding.

Penny: For the last leg of our honeymoon, we went to Rome. We spent about two weeks at this great short-term rental, Gio Roma, right by the Colosseum. We didn’t plan anything; we just wandered the streets all day and night.

George: I’ll never forget the honeymoon. It was amazing to celebrate with everyone, but it was romantic to spend time alone.

Penny: I remember every moment of the wedding and honeymoon vividly. There’s not one thing I’d change.

George: Now that we’re a married couple, we can continue to admire how much progress we’ve each made since we were teenagers. We’ve been there for each other since the beginning, so I have no trouble trusting that we’ll be there for each other through anything that may lie ahead.

Cheat Sheet

Date: October 5, 2022
Venue: Dimora delle Balze in Sicily, Italy
Bride’s wedding dress: Berta, with shoes by Amina Muaddi
Groom’s tux: Custom tuxedo from Suit Supply and shoes from Harry Rosen
Wedding guests: 33
Photographer: Giuseppe Marano
Hair and makeup: Brittany Sinclair
Wedding planner: Julia & Evita
Flowers: Intrecci di fiori d’arte
Music: Sicilian folk band Domo Emigrantes for the ceremony, cocktail and seated dinner, and a DJ afterward
Caterer: In-house by the kitchen team at Dimora delle Balze
Stationery: Paula Lee Calligraphy