Boston Date Night Series: Dinner at Seasons 52 in Chestnut Hill Square

For date night this week, we wanted to do something simple. It was a busy week and I was still recovering from a lingering cold – a nice dinner felt like the best plan. However, we still wanted to keep things exciting, so Darren found a place we hadn’t been before, but had good reviews on. Upon the recommendation of his dad, we headed over to Seasons 52 in Chestnut Hill Square for some fresh eats from their winter ’18 seasonal menu!

Before our 7:00 PM reservation, we decided to wander around The Shops at Chestnut Hill. As a Simon Mall, the stores are definitely higher end. There is everything from Madewell and J.Crew to Coach and Michael Kors. The anchor store is Bloomingdale’s, and it was fun walking through the evening gown section just for laughs. We captured a quick snap of my outfit for the night right before heading over to dinner. Details below!

Sweater: Madewell // Bodysuit: Aerie // Skirt: Wild Fable at Target // Boots: Vince Camuto // Purse: Kate Spade SATURDAY

When we entered the restaurant, the lobby was packed! It was a Saturday after all, so everyone was enjoying a night out. We gave our name and stood in the front corridor to wait. Just a few minutes after we arrived, one of the hostesses walked by leading a another party to their table and did a double take at Darren. When she came back through, she stopped and said, “Hey, do you work at Emmanuel?” As it turns out, she is a Biology student in one of the labs Darren preps at work. After making the connection, she was kind enough to bump our names up to the top of the waiting list and lead us to our table immediately. Bianca – if you’re reading this, thank you so much! You made our night!

The service at Seasons 52 overall was great! Our waitress was SO nice (more on this later) and all of our food was ready super quick despite the restaurant being so busy. This place really knows how to treat their guests!

After browsing their incredible menu, Darren and I settled on the Garlic Pesto Chicken Flatbread to start. The pesto was tangy and yummy, and the plate was perfect to share. For our main course, Darren went for Southern-Style Shrimp and Grits with chorizo, bacon, stone ground cheddar grits. I had the Wood-Grilled Pork Tenderloin with spiced cauliflower, sweet potato mash, shallot-herb jus. It was cooked to perfection (I like it medium well) and so delicious!

Last comes my favorite part: the dessert! At Seasons 52, the waitstaff brings a tray of incredible options, all served in shot glasses. Our selection that night was Belgain Chocolate S’More, Key Lime Pie, Mocha Macchiato, Pecan Pie, Poached Pear Cheesecake, and Raspberry Chocolate Chip Cannoli. Darren grabbed the Key Lime Pie with pecan crust and toasted meringue. I opted for the Raspberry Chocolate Chip Cannoli with ricotta and mascarpone, chocolate chips, raspberry sauce, and a cinnamon cannoli shell. It was fabulous, but I honestly wanted to try them all!

Before I sign off on this post, I have to give a shout out to our waitress, Juliet. She was incredibly kind the entire night, providing great suggestions from the menu and making sure we had everything we wanted. She also noticed that I had my Nikon with me and was taking photos, so she asked about what we do. When I told her I was a blogger, she had me write down my website on her notepad and she offered to take some fun shots of both Darren and I picking out our desserts (see below). As a painter/photographer studying and teaching in the local area, she was really excited to see us bringing a real camera out and about, as most people just use their phones. I really appreciated her contributing these great photos to this post. Thank you, Juliet!