Grilled Pineapple and Chicken Quesadillas

These Grilled Pineapple and Chicken Quesadillas are easy and delicious!

In the past three weeks we’ve scared away three babysitters. I’m starting to question if my parenting skills are really that bad or if my two-year-old Wes is just the sweetest devil you’ll ever know.

Babysitter #1: I texted her and told her we were on her way home from our date and asked if the boys were asleep (we took baby Gracie with us). She said she “Um…no. I actually had to call my mom because it got that bad.”  Great. She said in her Southern drawl that Wes had ripped off all of his clothes and was “nek-ked” yelling at her and running around the house refusing to do anything she said.

Although embarrassing, it wasn’t all that surprising to me. Wes often finds his clothes restricting and tries to get naked whenever we aren’t looking. And I can’t say it would be the first naked defiant tantrum that he’s thrown. He’s two and good at it. I chalked up the situation to the inexperience of a 16-year-old to handle a grouchy two-year-old and moved on.

Babysitter #2: I was really nervous about leaving my baby for the first time but we were headed to a work event for my husband and bringing a baby just wasn’t appropriate.

The babysitter was a 25-year-old who is a full-time nanny for a family with 3 children so I figured she could handle it. After many discussions about whether she was comfortable watching my three boys and a 5-month old she said “Oh yeah, I can handle it.”

After being gone for one hour I got a text from her saying, “I can’t handle this. I called my mom to come hold the baby.” I guess baby Gracie wouldn’t stop crying and missed her mama. So I headed home thinking, “Am I supposed to pay her and her mom?”

Babysitter #3: Itstarted off well. I didn’t dare leave Gracie after the last fiasco so we took her with us with some friends to the movies. She’s really good and never makes a peep as long I’m holding her.

Halfway through the movie the babysitter calls. “Um…Wes locked me in his bedroom and I can’t get out.”

We switched the door handle on his bedroom so that the lock is on the outside and she had tried to get him in his room to read a book and he locked her and the other boys in there. Smart and mischievous are a bad combination.

So that’s it. I’ve decided to never leave the house again. Ever.

These Grilled Pineapple and Chicken Quesadillas are easy and delicious!
 These Grilled Pineapple and Chicken Quesadillas were definitely my kid’s favorite dish from “Get Your Grill On” week. Sweet pineapple with cheese and chicken in a buttery tortilla really is a great combination.
Grilled pineapple is one of our favorite healthy desserts. The natural sugars start to caramelize and it turns into a delicious treat.

Layer your tortilla with chicken and slices of pineapple. Top it with additional BBQ sauce. You could add jalapenos here for some added kick but our BBQ sauce was pretty spicy so it didn’t need anything.

Grilled Pineapple and Chicken Quesadillas
  • 8 whole flour tortillas
  • butter
  • 2 cups grilled pineapple , sliced
  • 3 skinless , boneless chicken breasts pounded thin or butterflied
  • salt and pepper , to taste
  • 3 cups shredded Monterey Jack cheese
  • 3 tablespoons spicy barbecue sauce
  • (optional) cilantro and jalapenos
  1. To grill pineapple: Cut wedges, stick on skewers, and grill over low heat either on a grill, grill pan, or even a skillet. Cut into slices.
  2. Sprinkle chicken with salt and pepper and Cajun spice if you want some heat. Spray grill with cooking spray and grill on both sides until done, brushing with barbecue sauce after it's finished. Set aside and slice into very thin slices.
  3. Warm pan over medium heat and put butter in the pan enough to coat. Slightly warm and toast tortillas on both sides, then remove from griddle and set aside.
  4. To assemble, sprinkle four browned tortillas with grated Monterey Jack and arrange chicken slices and pineapple slices evenly over the surface. If desired, add sliced jalapenos and cilantro here. Drizzle extra barbecue sauce over the top. Add second browned tortilla on top of each one. (You'll have four complete quesadillas at this point.)
  5. Add quesadillas back to skillet to warm, until cheese is melted. Cut each quesadilla into six wedges. Serve with sour cream, pico de gallo, and lime wedges.
Recipe Notes
Source: The Pioneer Woman


Speak Your Mind



  1. As both a babysitter that was terrorized, and someone who took her turn torturing babysitters, I think it comes with the territory that kids will act out when Mom and Dad aren’t there! Do you have any friends with kids who are old enough to watch yours? Maybe a couple of teens that your kids know? It always worked best when I knew the children I was watching, as I knew what to expect and they knew me.
    However, reading your stories def had me smiling… I kinda miss those days!

  2. As someone who babysat for years, I hope you can find someone who has no fear and just emphasis the chaos. I always found if I decided we were going to have fun and tried to just play with them and not “be in charge”, it works a bit better. Though, I did once have two boys hide for me in a house for an hour and half. It was awful.

  3. Sorry about the babysitters! I never leave anymore and I only have little guy. Your quesaddilas lokked delish, I make something similar with mozzarella and green peppers.

  4. The woes of babysitting. I used to babysit a boy who loved to strip down and chase his little sister around the house. He refused to listen until I picked up the phone and threatened to call his parents. Worked every time!

    The grilled pineapple looks fab! I would have never thought to try that.

  5. Buwahahahaha. You reminded me why I never leave the house alone. And why “date night” is a thing of the past. With two kids and a baby, I’ve come to terms with the fact that it will be several years before going out without at least one of them in tow is pretty much out of the question. This post was too funny.
    Oh – and the quesadillas sound yummy. I think grilled pineapple is good on ANYTHING!

  6. Hahaha this made my night. I just have a six month old and I have only left her with my MIL and my mom. And apparently she just screams the whole time. So this made me feel a little better that I’m not the only one! But at least leaving her with experienced moms helps a little, they seem to handle it a little better and are used to babies crying.

  7. I’m lucky to have family to babysit, otherwise I’m not sure we would go anywhere! Funny story! Love the quesadillas. I like pineapple in savory dishes.

  8. LOL Thankfully, my kids have never stripped down naked to have tantrums. Oh no, they stay fully clothed for them. LOL My kids are 8, 6 and 4.

  9. I loved your post! My son also finds his clothes restrictive and is always asking for permission to be able to take off his shirt, at least. Keep trying with the sitters. You will find your Mary Poppins.

  10. Things will get easier. I remember those days and now my kids are 18 and 19. It happens to everyone. Hang in there!
    The food looks great! I am going to have to throw a pineapple on the grill now! yum!

  11. Those sound so good, I cannot wait to try them!! I think I would add green pepper and onion to make a truley Hawaiian experience;) Good luck with the babysitter issue. I would do a babysitting swap when we lived in Denver so that might be another option.

  12. Hahaha, what a smart little guy locking her in his bedroom!

  13. Oh my gosh, this just made me laugh. Good luck in finding someone that can with stand it. You need your away time to! 🙂

  14. I love your blog for the fabulous, tasty recipes, but especially for your awesome anecdotes at the beginning! Good luck with silly boy, Wes! I bet he’s so fun…when he’s not nekked and yelling 🙂

  15. These were delicious! I threw these together prior to a 6pm softball game. Took a shortcut and bought the expensive pre-grilled chicken pieces, canned pineapple. I grilled the pineapple and left the grill on. Threw the quesadillas together and then put them on the grill for a couple of minutes a side. Wonderful. Enjoyed by the whole family. Thanks for another great one!

  16. Too funny! Kids are so mischievous, but I think that is a good thing! My siblings and I were horrible to our babysitters when we were kids, and I am sure that our kids will be babysitter terrors too! Oh, and you can never go wrong with grilled fruit!

  17. This made me laugh and brought back memories of babysitter nightmares. Admittedly, my kids are difficult. One time, years ago, I hired two sitters for my three daughters, ages 6 months, 2, and 5. After two hours we returned home to find they (babysitters and kids) had played dress-ups with my clothes. All of my clothes were off the hangers and strewn across the entire house. Furniture had been rearranged (some in the upside down position). It was a disaster. I paid them both (not sure why) and they said, ‘Thanks, be sure to call us again!’ Ummm, no. The other really bad time was when I pulled into my very long driveway and could see and smell smoke pouring out of the house. I ran inside to find that the sitter had cooked a corn dog in the microwave for 7 minutes instead of 70 seconds and nearly caught the house on fire. We quit going out. Now we have six kids and one is finally old enough that we can put all the littles to bed and leave the older one in charge and go out for a really late dinner…

  18. this made me laugh so hard— i have a 2 year old who makes a pretty good one as well— i keep telling my husband we need to turn the locks around, but now that your son has done that, i guess i should be glad we haven’t done it! who needs doors anyways?? let’s just take them off! (except for my closet door so i can still sneak my chocolate)

  19. I made this for dinner last night, and it is now one of my all time favorite dishes!!! I loved it AND my husband loved it. My 4 year old wouldn’t try it all together, but ate a lot of the chicken and pineapple separately. Thanks for sharing this recipe!!!!

  20. Oh my goodness! I couldn’t stop laughIng! I have 7 kids, the last two are very close, two little “surprises”!!!! Your son sounds like no. 6 was a few months ago and what no. 7 aspires to be!!!! LOL

  21. Tried ’em. Loved ’em. And the hubs REALLY loved them! So easy- I used a chipotle barbecue sauce. Thanks! They were delish!

  22. Dk6qqG I really enjoy the article.Much thanks again. Much obliged.

  23. After being a nanny for almost 5 years this post definitely cracked me up. I love kids, but man, they really can be little devils haha. Also, this ques looks AMAZING! I could easily eat 3.