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Grilled Cheese Tomato Sandwich

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Grilled Cheese Tomato Sandwich. The only way to eat a grilled cheese in my opinion. And with wine of course. “You know you have made it in life when you have a refrigerator full of cheese” – Kristin Lilly 

This is going to be a tough post to write. But I need to, it’s time.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

It was December, I want to say the year was 1997 or 1998. We were driving down her dad’s mile long driveway in her white Mazda Miata with the top down like we always did. We were of course bundled up in jeans, sweaters and ugg boots. Winter in Southern California was never cold, but to Californians anything close to 60 is freezing. And since we were silly enough to dive with the car’s top down, we bundled up and had the heat on. I know, we were silly. The house was decorated beautifully for the holidays. Professionals were hired by her dad to decorate that would put any department store to shame. I loved going to her dad’s house at the holidays because of the decorations. He spared no expense, he went all out.

We parked her Miata in front of one of his three garages ( yes three, the place was massive)  under a giant wreath and walked in through the back mud room doors. We were stopped in our tracks when we saw how many gift baskets were piled up on the table and chairs in the adjacent laundry room Kristin with her giant blue eyes wide open turned to me and said “Ohhhhhh. Gift baskets for my dad. You know what this means right?”  I shook my head not having a clue what she was going to say next. ” This means cheese. I LOVE cheese. And you know you have made it in life when you have a refrigerator full of cheese” She then added ” Let’s make grilled cheese tomato sandwiches, I’m starving” Yum.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

She walked through to the kitchen and over to the massive Sub-Zero side by sides and opened the fridge. I kid you not, she dropped to her knees. The fridge was FULL of cheese. Every kind of cheese you can think of. She grabbed up a bunch and hugged it. Giggling she exclaimed “I’ve made it. I have finally made it. I have all the cheese in the world”  We gathered up supplies to make grilled cheese tomato sandwiches with some crusty sourdough bread, ripe tomatoes and a variety of cheese. She introduced me to gruyere, havarti, and fontina cheeses. She showed me a huge variety of blue cheese that she loved and I didn’t care for at all. We then looked around to see where her dad was, he was in his office across the yard by the pool. The most amazing pool ever. A black bottom free form pool with two hot tubs and a bunch of free form rocks and palm trees.

It was designed after one of the seven sacred pools of Hawaii and her dad’s office was the poolhouse. We walked in and said hi, told him we were making sandwiches and asked if he wanted one. He said he was busy working so we ran back to the main house and immediately snuck over to his hidden wine closets. He had the coolest house ever. There were two wine closets near the front entrance of the house and if you didn’t know that they were there you wouldn’t have ever guessed. They were secret closets that just looked like walls with alcoves for large vases he had as decorations. If you looked closely you could see a seam by one corner and a gentle push would reveal the hidden room. It was awesome.  We stole out a couple bottles of chardonnay and a bottle of Dom Perignon to take back to our house later to share with the cute boys that lived next door. We were fancy like that.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

I started in on slicing tomatoes while she got out a cookie sheet. She told me that the best grilled cheese tomato sandwiches are started on a griddle pointing to the giant Wolf range in her dad’s massive kitchen, and then finished in the oven. Wolf ovens of course.  I made a mental note to one day own Wolf appliances.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

She sliced up a bunch of different cheeses to make us a cheese plate to nibble on while making the sandwiches and she poured a couple glasses of chardonnay. Chardonnay isn’t my favorite, but it was hers. She said that the best way to eat a grilled cheese tomato sandwich was with a crisp, cold glass of chard. I obeyed. She was the closest thing to being a big sister to me so I paid close attention to the wisdoms of life she was always passing down to me. Tucking them away for future reference.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

LOTS of butter, she told me. That is the key to making the bread extra crisp. This isn’t health food, you know. Its bread full of melty cheese, might as well add on lots of butter. Especially since we were going to be drinking chardonnay and or champagne with the sandwiches.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

Perfect grilled cheese tomato sandwiches.  We ate our sandwiches and sipped our wine all while she told me about how much she just truly loves cheese. All of a sudden we heard a ton of noise and in came running her 5 year old half brother, Parker. I LOVED Parker. He was a messy, loud, funny little boy. I would babysit him on occasion. He had nicknamed me “Moo” for whatever reason and when he saw me he came running over yelling “MOOOOO!!!” and gave me a huge hug. He then hugged Kristin and ran off to his room. We hung out for a little while longer, took one of the gift baskets from the laundry room, filled it with a ton of the cheeses from the fridge, put our bottles of wine and very expensive champagne in a bag and took off in the Miata to head back to our little house. She had the biggest smile when she loaded up our fridge with all the cheese we pilfered from her dad.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

It was a cool little beach house that we shared. My bedroom was in the front house and the back studio was her bedroom, which was really a giant room with a giant closet. No kitchen or full bathroom.  The main house had the kitchen and bathroom with the shower. We used the spare room as storage and extra closet space. We had found clothes racks that you would find at a department store and used those as extra storage. There was a covered patio that doubled as our laundry room and where her dogs slept on an old leather sofa. The front room was pretty small but we could see the cute boys that lived next door and whenever they saw we were around they would come over to visit.   When I turned 21 Kristin wanted to take me out for a proper and classy birthday. Not a get drink, get wasted and puke birthday. She was dating the head bartender of a bar in town, O’Malleys, that is or was famous for its guest bartender on St. Patrick’s Day. The basketball player Michael Jordan would guest bartend that night. Not sure if he still does, but he used to. After we got all dolled up and ready to hit the town. Kristin had made dinner reservations at another place for sushi and drinks. My first legal drink was a raspberry cosmopolitan. It was so good. After dinner we headed over to O’malleys where Eric, her bartender boyfriend, poured me a Manhattan. I was all about classy martini drinks that night. It was such a fun birthday. We ate, drank, laughed lots, danced with cute guys, and I never got sick. I wasn’t even hung over. It was fantastic.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

A few years later I finished  my X-ray tech degree at Santa Barbara City College and had gotten accepted into Ultrasound school at the University of Colorado Hospital. It was 2003. It had been a little while since I had spoken to Kristin. We spoke often but with her moving back east to Boston to be closer to her brothers and me moving to Colorado some time had passed between chats. As in several weeks rather than every day. I was walking through Kohls when I got a phone call from her. I was telling her how I was buying items to furnish my apartment. I was getting dishes, glasses and utensils for my small apartment kitchen, a few items for the rest of the place. I remember her clearly “Ahhh my little sis. All grown up, shopping like a responsible adult. I am so proud of you”.  We talked about how we missed each other and how I wanted to come visit her in Boston. I had never been and her brothers were a blast to hang out with. We ended the conversation with tentative plans for me to visit over my spring break.

December 2003. I was in Vail driving with my (now ex) boyfriend to his house when I got a call. It was my mom. She asked me if I was alone. “Why? I asked” “I would rather tell you this news when you were with someone” I told her I wasn’t alone. Then I had this feeling that her news was really bad ” Who died?” I asked. I could tell my mom had been crying. “I am so sorry. Its Kristin. I opened the paper this morning and I was staring at her obituary”.  The rest of that day was a blur. I remember being in shock. Denial. Anger. More shock. And complete and utter sadness.


I called her dad. He told me she took her own life.  Overdose on pain and sleeping pills. He had been trying to locate me to tell me. My best friend in the whole entire world suffered from depression and even I didn’t know it she hid it so well. But her demons got the best of her and she took her own life. She was only 34.


She was the happiest person I knew. At least I thought. Her dad told me that in early high school she had several suicide attempts. This was before I knew her. She grew up in upstate New York. Ithaca to be exact. Her parents divorced when she was in her early teens, her dad moving out to California, mom stayed in New York. Kristin went to Penn State on a full ride for swimming then came out to California to train on the swim team I was on so she could be trained by our coach for the Olympic trials. She was an amazing swimmer. I wanted to be as good as she was. Kristin was 6′ tall, long blonde hair and super tan. You would have never guessed she wasn’t a native Californian. People always thought were were sisters since I was 2 inches shorter but same long blonde hair and had that Southern California beach girl look as well.  Kristin ran the kids swimming program. Kids LOVED her. She was so bubbly and happy. When she moved back to Boston she went to work at a local pool and started the kids swim program. She brought it from no kids to 300. She was truly happy there. Or so I thought. She was filling a void that nothing could ever truly fill.

Today is the anniversary of her death and not a day goes by that it doesn’t hurt that she is gone. When I got married I wished she could have been there. When I had my first daughter I wished she had been there to know I named her after her. My first daughter’s middle name is Lilly, Kristin’s last name.    I wanted so badly to call her the day I got cheese in the mail from Kerrygold to tell her that I made it, that I get paid in cheese to do my work. I know how proud she would have been. I can hear her now “Shanna!!  In her high pitched silly voice she would make. “I am so prooouudddd of you!!”

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

Kristin loved sunflowers. She said they were happy flowers. Whenever we would go to the farmers market she would always buy fresh sunflowers to put in vase on our table in the house. I painted a giant picture of sunflowers that she had hung in our bathroom. When I moved out she kept the painting and I always wonder what became of that painting. To this day I can’t look at sunflowers without thinking about her. And I can’t ever eat a grilled cheese tomato sandwich without thinking of that day at her dad’s house when we saw all that glorious cheese and she taught me the true meaning of cheese. At least her meaning. And I can’t have a grilled cheese tomato sandwich without a glass of chardonnay. It really does make the sandwich that much better. I also now own Wolf appliances. Still working on figuring out how to afford and find space for the side by side sub zeros, but I know Kristin would be so happy for me that I finally have my giant Wolf range top and double ovens. And I know she would hope that my fridge was always full of cheese. Which I do have a cheese drawer that is always full.

Grilled Cheese Tomato Sandwich www.pineappleandococonut.com

In memory of Kristin Elizabeth Lilly. 1969-2003.  Kristin, I miss you.


Yield: 1-10

Grilled Cheese and Tomato Sandwich

Grilled Cheese and Tomato Sandwich

Grilled then baked makes the bread on these sandwiches perfectly crispy. Several kinds of cheese and fresh tomatoes are used and be sure to serve with a cold glass of chardonnay.


  • Thick sliced bread such as sourdough or ciabatta
  • Cheese - 3 to 4 different kinds, sliced thin. Good melting cheeses such as Havarti, cheddar, gruyere, fontina, jack, swiss.
  • Tomatoes, sliced
  • Butter, softened


  • Preheat griddle and preheat oven to 400 Deg. F. Generously spread butter on one side of two slices of bread. Layer a few slices of cheese on one slice of the bread, top with tomato slices, then more cheese. Top with the other slice of buttered bread. Repeat with remaining slices of bread, cheese and tomato for how many sandwiches you are making. Place on griddle and grill until the butter is starting to melt and bread is a little golden, about 2 minutes. Repeat on other side. Place sandwiches on a cookie sheet and place in oven until the cheese is super melty and the bread is golden brown, about 4 minutes, watching carefully so they don't burn. Remove from oven, slice and serve hot.
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    Suicide is so devastating. It is a public health crisis. And not everyone gets the help they need when they are suicidal. My friend Kristin had been seeking help, getting regular counseling, taking meds. But unfortunately she was beyond help. And no one knew it. If you know someone who is depressed and or suicidal be there for them. They do need the help. Even if it’s only for a little while. Not all suicides can be prevented, but many can. There are many ways to help a friend or family member in need. There are many centers for suicide prevention and counselors and therapists that can help. The Suicide Prevention Lifeline could just be that one step to saving someone’s life. Their national number is 1-800-273-8255. I only wish I could call it to bring back Kristin to life.

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