Preheat oven to 400 degrees and bring a pot of water to a boil on the stove.
Spread the broccoli florets on a baking sheet and top them with the bacon pieces. Roast the broccoli and bacon for 15 minutes. While the broccoli roasts, cook the tortellini according to package directions. Drain and cool the pasta to room temperature.
After 15 minutes, stir the broccoli around on the baking sheet to coat it in the bacon fat and continue roasting it for 5 to 10 minutes or until the broccoli is lightly caramelized and fork tender. Set the broccoli and bacon aside to cool.
To make the dressing, combine the olive oil, lemon juice, salt, and pepper in a small bowl.
Rub the garlic all over the inside of the serving bowl. This will work on any type of bowl - wood, plastic, or glass. Place the broccoli, bacon, pasta, tomatoes in the bowl and gently toss them together. Add the dressing and toss it all again before serving.
Notes
I think this salad is best the day it's made and served at room temperature. You can stick it in the fridge for a little bit to slightly chill it, but if it gets too cold the dressing will dry out and the tomatoes will have a different (not so great) texture. If you want to serve it cold I recommend keeping the components separate until you are ready to serve it. Also, keep the tomatoes at room temperature and add them once you're ready to serve.